JP3195361B2 - ビシクロ環系アミノ誘導体およびそれを含有するpgd2拮抗剤 - Google Patents
ビシクロ環系アミノ誘導体およびそれを含有するpgd2拮抗剤Info
- Publication number
- JP3195361B2 JP3195361B2 JP50372497A JP50372497A JP3195361B2 JP 3195361 B2 JP3195361 B2 JP 3195361B2 JP 50372497 A JP50372497 A JP 50372497A JP 50372497 A JP50372497 A JP 50372497A JP 3195361 B2 JP3195361 B2 JP 3195361B2
- Authority
- JP
- Japan
- Prior art keywords
- chcl3
- 300mhz
- cdcl3
- meoh
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000005557 antagonist Substances 0.000 title claims abstract description 19
- BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 0.000 title claims abstract description 4
- 102100029100 Hematopoietic prostaglandin D synthase Human genes 0.000 title claims abstract 3
- 101000988802 Homo sapiens Hematopoietic prostaglandin D synthase Proteins 0.000 title claims abstract 3
- BHMBVRSPMRCCGG-UHFFFAOYSA-N prostaglandine D2 Natural products CCCCCC(O)C=CC1C(CC=CCCCC(O)=O)C(O)CC1=O BHMBVRSPMRCCGG-UHFFFAOYSA-N 0.000 title claims abstract 3
- 150000001412 amines Chemical class 0.000 title description 4
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- 150000003839 salts Chemical class 0.000 claims abstract description 33
- 239000003814 drug Substances 0.000 claims abstract description 13
- -1 thiophenediyl Chemical group 0.000 claims description 162
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 14
- 150000002431 hydrogen Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000004043 oxo group Chemical group O=* 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 7
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 229940124597 therapeutic agent Drugs 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 206010028735 Nasal congestion Diseases 0.000 claims description 4
- 125000000676 alkoxyimino group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 4
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
- 125000005905 mesyloxy group Chemical group 0.000 claims description 4
- 125000004957 naphthylene group Chemical group 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 229940079593 drug Drugs 0.000 abstract description 6
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- 208000024998 atopic conjunctivitis Diseases 0.000 abstract description 3
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- 208000024780 Urticaria Diseases 0.000 abstract 1
- 208000027418 Wounds and injury Diseases 0.000 abstract 1
- 230000020411 cell activation Effects 0.000 abstract 1
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- 208000035475 disorder Diseases 0.000 abstract 1
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1184
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 742
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 697
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 80
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 238000009739 binding Methods 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 230000027455 binding Effects 0.000 description 9
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- 150000001735 carboxylic acids Chemical class 0.000 description 8
- 102220240796 rs553605556 Human genes 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 210000004623 platelet-rich plasma Anatomy 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 102000005962 receptors Human genes 0.000 description 7
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- 150000003460 sulfonic acids Chemical class 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
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- 239000000725 suspension Substances 0.000 description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 5
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 108010058846 Ovalbumin Proteins 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
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- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
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- 150000002170 ethers Chemical class 0.000 description 3
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- YURNCBVQZBJDAJ-UHFFFAOYSA-N heptenoic acid group Chemical class C(C=CCCCC)(=O)O YURNCBVQZBJDAJ-UHFFFAOYSA-N 0.000 description 3
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- ZBNLHDTZKLXXJV-RGCAIDKMSA-N (z)-7-[(1s,2r,3r,4r)-3-[(4-phenylbenzoyl)amino]-2-bicyclo[2.2.1]heptanyl]hept-5-enoic acid Chemical compound N([C@@H]1[C@]2([H])CC[C@@](C2)([C@H]1C\C=C/CCCC(O)=O)[H])C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 ZBNLHDTZKLXXJV-RGCAIDKMSA-N 0.000 description 2
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- FKJARBPQBIATJT-UHFFFAOYSA-N n-benzyl-n-phenylaniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC=CC=1)C1=CC=CC=C1 FKJARBPQBIATJT-UHFFFAOYSA-N 0.000 description 1
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- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000011574 phosphorus Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
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- 239000003755 preservative agent Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- YIBNHAJFJUQSRA-YNNPMVKQSA-N prostaglandin H2 Chemical compound C1[C@@H]2OO[C@H]1[C@H](/C=C/[C@@H](O)CCCCC)[C@H]2C\C=C/CCCC(O)=O YIBNHAJFJUQSRA-YNNPMVKQSA-N 0.000 description 1
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- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
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- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000007929 subcutaneous injection Substances 0.000 description 1
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- 229960002317 succinimide Drugs 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
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- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
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- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/52—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C233/63—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
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- C07C233/74—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
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- C07C233/82—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/84—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of a saturated carbon skeleton containing rings
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/18—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides
- C07C235/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
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- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/36—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C235/54—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
【発明の詳細な説明】 技術分野 本発明は、ビシクロ環系アミノ誘導体およびそれらを
含有するプロスタグランジンD2(以下、PGD2という)拮
抗剤に関する。
含有するプロスタグランジンD2(以下、PGD2という)拮
抗剤に関する。
背景技術 本発明に関わるビシクロ環系アミノ誘導体の一部のも
のはトロンボキサンA2(TXA2)拮抗剤として有用である
ことが知られている(特公平5−79060号明細書)。し
かしながら、特公平5−79060号に記載された化合物に
ついては、いずれもTXA2拮抗剤としての有用性が開示さ
れているにすぎず、本発明で明らかにされたPGD2拮抗剤
としての用途については、何ら示唆されていない。
のはトロンボキサンA2(TXA2)拮抗剤として有用である
ことが知られている(特公平5−79060号明細書)。し
かしながら、特公平5−79060号に記載された化合物に
ついては、いずれもTXA2拮抗剤としての有用性が開示さ
れているにすぎず、本発明で明らかにされたPGD2拮抗剤
としての用途については、何ら示唆されていない。
即ち、TXA2は、その作用として血小板凝集作用、血栓
形成作用等があることが知られているが、TXA2拮抗剤
は、TXA2に拮抗することで、抗血栓剤、心筋梗塞、喘息
の治療剤として有用であると考えられている。
形成作用等があることが知られているが、TXA2拮抗剤
は、TXA2に拮抗することで、抗血栓剤、心筋梗塞、喘息
の治療剤として有用であると考えられている。
一方、本発明のPGD2拮抗剤は、PGD2の生産過多に起因
する症状の改善、さらに詳しくは、肥満細胞機能不全が
関与する疾患、例えば全身性肥満細胞症及び全身性肥満
細胞活性化障害の治療剤、さらには抗気管収縮剤、抗喘
息剤、抗アレルギー性鼻炎剤、抗アレルギー性結膜炎
剤、抗蕁麻疹剤、虚血再灌流傷害治療薬、抗炎症剤とし
て有用である。
する症状の改善、さらに詳しくは、肥満細胞機能不全が
関与する疾患、例えば全身性肥満細胞症及び全身性肥満
細胞活性化障害の治療剤、さらには抗気管収縮剤、抗喘
息剤、抗アレルギー性鼻炎剤、抗アレルギー性結膜炎
剤、抗蕁麻疹剤、虚血再灌流傷害治療薬、抗炎症剤とし
て有用である。
上記から明らかなように、TXA2拮抗剤とPGD2拮抗剤
は、その作用点、機序が異なると共に、適応も異なり、
全く異なる性質のものであることから、ある化合物がこ
れらの作用を同時に有するということは、まったく予測
し得ないことであった。
は、その作用点、機序が異なると共に、適応も異なり、
全く異なる性質のものであることから、ある化合物がこ
れらの作用を同時に有するということは、まったく予測
し得ないことであった。
PGD2は肥満細胞から産生遊離される最も主要なプロス
タノイドであり、免疫学的あるいは非免疫学的刺激によ
り活性化されたシクロオキシゲナーゼ(cyclooxygenas
e)により、アラキドン酸(arachidonic acid)からPGG
2、PGH2を経て産生される。PGD2は種々の強力な生理
的、病的な作用を有し、例えば、強い気管収縮を起こし
気管支喘息の病態を形づくる。さらに全身性アレルギー
状態においては末梢血管を拡張しアナフィラキシーショ
ックの原因となる、などである。とりわけPGD2をアレル
ギー性鼻炎の鼻閉症状の発現の原因物質の一つであると
する考えが注目を集めている。そのため、鼻閉症状の軽
減を目的とする薬物としてPGD2の生合成阻害剤、あるい
は受容体拮抗剤の開発が考えられている。しかし、PGD2
の生合成阻害剤は他の生体内でのプロスタグランジン類
の合成に大きな影響を及ぼす可能性があることから、PG
D2受容体に特異的な、PGD2受容体拮抗剤(遮断薬)の開
発が望まれている。
タノイドであり、免疫学的あるいは非免疫学的刺激によ
り活性化されたシクロオキシゲナーゼ(cyclooxygenas
e)により、アラキドン酸(arachidonic acid)からPGG
2、PGH2を経て産生される。PGD2は種々の強力な生理
的、病的な作用を有し、例えば、強い気管収縮を起こし
気管支喘息の病態を形づくる。さらに全身性アレルギー
状態においては末梢血管を拡張しアナフィラキシーショ
ックの原因となる、などである。とりわけPGD2をアレル
ギー性鼻炎の鼻閉症状の発現の原因物質の一つであると
する考えが注目を集めている。そのため、鼻閉症状の軽
減を目的とする薬物としてPGD2の生合成阻害剤、あるい
は受容体拮抗剤の開発が考えられている。しかし、PGD2
の生合成阻害剤は他の生体内でのプロスタグランジン類
の合成に大きな影響を及ぼす可能性があることから、PG
D2受容体に特異的な、PGD2受容体拮抗剤(遮断薬)の開
発が望まれている。
発明の開示 本発明者らは、PGD2受容体に特異的なPGD2受容体拮抗
剤(遮断薬)を開発するために鋭意、研究した結果、下
記一般式(I)で示される化合物またはその塩がPGD2受
容体拮抗剤として強力な作用を有し、かつ化学的、生化
学的に安定な化合物であることを見い出し、本発明を完
成するに至った。
剤(遮断薬)を開発するために鋭意、研究した結果、下
記一般式(I)で示される化合物またはその塩がPGD2受
容体拮抗剤として強力な作用を有し、かつ化学的、生化
学的に安定な化合物であることを見い出し、本発明を完
成するに至った。
即ち、本発明は、式(I)で示される化合物もしくは
その塩またはそれらの水和物を有効成分として含有する
PGD2拮抗剤を提供するものである。: を表わし、 Aはヘテロ原子もしくはフェニレンを介在していてもよ
く、オキソ基を有していてもよく、および/または不飽
和結合を有していてもよいアルキレン; Bは水素、アルキル、アラルキルまたはアシル; RはCOOR1、CH2OR2またはCON(R3)R4; R1は水素またはアルキル; R2は水素またはアルキル; R3およびR4はそれぞれ独立して水素、アルキル、ヒドロ
キシまたはアルキルスルホニル; X1は単結合、フェニレン、ナフチレン、チオフェンジイ
ル、インドールジイルまたはオキサゾールジイル; X2は単結合、−N=N−、−N=CH−、−CH=N−、−
CH=N−N−、−CH=N−O−、−C=NNHCSNH−、−
C=NNHCONH−、−CH=CH−、−CH(OH)−、−C(C
l)=C(Cl)−、−(CH2)n−、エチニレン、−N
(R5)−、−N(R51)CO−、−N(R52)SO2−、−N
(R53)CON(R54)−、−CON(R55)−、−SO2N(R56)
−、−O−、−S−、−SO−、−SO2−、−CO−、オキ
サジアゾールジイル、チアジアゾールジイルまたはテト
ラゾールジイル; X3はアルキル、アルケニル、アルキニル、アリール、ア
ラルキル、ヘテロ環、シクロアルキル、シクロアルケニ
ル、チアゾリニリデンメチル、チアゾリジニリデンメチ
ル、−CH=NR6または−N=C(R7)R8; R5、R51、R52、R53、R54、R55およびR56は水素または
アルキル; R6は水素、アルキル、ヒドロキシ、アルコキシ、カル
バモイルオキシ、チオカルバモイルオキシ、ウレイドま
たはチオウレイド; R7およびR8はそれぞれ独立してアルキル、アルコキシ
またはアリール; nは1または2; Zは−SO2−または−CO−; mは0または1; これらの定義において、置換基が環状のものはニト
ロ、アルコキシ、スルファモイル、置換もしくは非置換
アミノ、アシル、アシルオキシ、ヒドロキシ、ハロゲ
ン、アルキル、アルキニル、カルボキシ、アルコキシカ
ルボニル、アラルコキシカルボニル、アリールオキシカ
ルボニル、メシルオキシ、シアノ、アルケニルオキシ、
ヒドロキシアルキル、トリフルオロメチル、アルキルチ
オ、−N=PPh3、オキソ、チオキソ、ヒドロキシイミ
ノ、アルコキシイミノ、フェニルおよびアルキレンジオ
キシから選ばれる1〜3個の基で置換されていてもよ
い) 発明を実施するための最良の形態 上記のPGD2拮抗剤となり得る化合物を更に具体的に示
せば、式(I)で示される化合物において、 を表わし、mが0であり、ZがSO2のとき、X1およびX1
がともに単結合であり、X3がアルキル、フェニル、ナフ
チル、スチリル、キノリルまたはチエニルを表わし、こ
れらの置換基のうち、環状のものがニトロ、アルコキ
シ、置換もしくは非置換アミノ、ハロゲン、アルキルお
よびヒドロキシアルキルから選ばれる1〜3個の基で置
換されていてもよい化合物もしくはその塩またはそれら
の水和物が挙げられる。
その塩またはそれらの水和物を有効成分として含有する
PGD2拮抗剤を提供するものである。: を表わし、 Aはヘテロ原子もしくはフェニレンを介在していてもよ
く、オキソ基を有していてもよく、および/または不飽
和結合を有していてもよいアルキレン; Bは水素、アルキル、アラルキルまたはアシル; RはCOOR1、CH2OR2またはCON(R3)R4; R1は水素またはアルキル; R2は水素またはアルキル; R3およびR4はそれぞれ独立して水素、アルキル、ヒドロ
キシまたはアルキルスルホニル; X1は単結合、フェニレン、ナフチレン、チオフェンジイ
ル、インドールジイルまたはオキサゾールジイル; X2は単結合、−N=N−、−N=CH−、−CH=N−、−
CH=N−N−、−CH=N−O−、−C=NNHCSNH−、−
C=NNHCONH−、−CH=CH−、−CH(OH)−、−C(C
l)=C(Cl)−、−(CH2)n−、エチニレン、−N
(R5)−、−N(R51)CO−、−N(R52)SO2−、−N
(R53)CON(R54)−、−CON(R55)−、−SO2N(R56)
−、−O−、−S−、−SO−、−SO2−、−CO−、オキ
サジアゾールジイル、チアジアゾールジイルまたはテト
ラゾールジイル; X3はアルキル、アルケニル、アルキニル、アリール、ア
ラルキル、ヘテロ環、シクロアルキル、シクロアルケニ
ル、チアゾリニリデンメチル、チアゾリジニリデンメチ
ル、−CH=NR6または−N=C(R7)R8; R5、R51、R52、R53、R54、R55およびR56は水素または
アルキル; R6は水素、アルキル、ヒドロキシ、アルコキシ、カル
バモイルオキシ、チオカルバモイルオキシ、ウレイドま
たはチオウレイド; R7およびR8はそれぞれ独立してアルキル、アルコキシ
またはアリール; nは1または2; Zは−SO2−または−CO−; mは0または1; これらの定義において、置換基が環状のものはニト
ロ、アルコキシ、スルファモイル、置換もしくは非置換
アミノ、アシル、アシルオキシ、ヒドロキシ、ハロゲ
ン、アルキル、アルキニル、カルボキシ、アルコキシカ
ルボニル、アラルコキシカルボニル、アリールオキシカ
ルボニル、メシルオキシ、シアノ、アルケニルオキシ、
ヒドロキシアルキル、トリフルオロメチル、アルキルチ
オ、−N=PPh3、オキソ、チオキソ、ヒドロキシイミ
ノ、アルコキシイミノ、フェニルおよびアルキレンジオ
キシから選ばれる1〜3個の基で置換されていてもよ
い) 発明を実施するための最良の形態 上記のPGD2拮抗剤となり得る化合物を更に具体的に示
せば、式(I)で示される化合物において、 を表わし、mが0であり、ZがSO2のとき、X1およびX1
がともに単結合であり、X3がアルキル、フェニル、ナフ
チル、スチリル、キノリルまたはチエニルを表わし、こ
れらの置換基のうち、環状のものがニトロ、アルコキ
シ、置換もしくは非置換アミノ、ハロゲン、アルキルお
よびヒドロキシアルキルから選ばれる1〜3個の基で置
換されていてもよい化合物もしくはその塩またはそれら
の水和物が挙げられる。
同様に、式(I)で示される化合物において、 を表わし、mが1のとき、X1およびX2がともに単結合で
あり、X3がハロゲンで置換されていてもよいフェニルで
ある化合物もしくはその塩またはそれらの水和物が挙げ
られる。
あり、X3がハロゲンで置換されていてもよいフェニルで
ある化合物もしくはその塩またはそれらの水和物が挙げ
られる。
同様に、式(I)で示される化合物において、 を表わし、mが1のとき、X1がフェニル、X2が−CH2−
または−N=N−であり、X3がフェニルである化合物も
しくはその塩またはそれらの水和物が挙げられる。
または−N=N−であり、X3がフェニルである化合物も
しくはその塩またはそれらの水和物が挙げられる。
同様に、式(I)で示される化合物は、式(I a): (式中、A、B、R、X1、X2およびX3が前記と同意義で
ある。
ある。
ただし、(1)X1およびX2が単結合であり、X3が置換
もしくは非置換フェニルまたはナフチル、および(2)
Aが5−ヘプテニレン、RがCOOR1(R1は水素またはメ
チル)、X1が1、4−フェニレン、X2が単結合、X3がフ
ェニルである場合を除く)で示される化合物もしくはそ
の塩またはそれらの水和物として例示される。
もしくは非置換フェニルまたはナフチル、および(2)
Aが5−ヘプテニレン、RがCOOR1(R1は水素またはメ
チル)、X1が1、4−フェニレン、X2が単結合、X3がフ
ェニルである場合を除く)で示される化合物もしくはそ
の塩またはそれらの水和物として例示される。
同様に、式(I)で示される化合物は、式(I b): を表わし、A、B、R、X1、X2およびX3が前記と同意義
である。ただし、X1およびX2が単結合であり、X3がフェ
ニルである場合およびX1が単結合でX2が−O−であると
き、X3がベンジルである場合を除く)で示される化合物
もしくはその塩またはそれらの水和物として例示され
る。
である。ただし、X1およびX2が単結合であり、X3がフェ
ニルである場合およびX1が単結合でX2が−O−であると
き、X3がベンジルである場合を除く)で示される化合物
もしくはその塩またはそれらの水和物として例示され
る。
更に具体的には、式(I a)で示される化合物におい
て、X1およびX2が単結合であり、X3がイソオキサゾリ
ル、チアジアゾリル、イソチアゾリル、モルホリル、イ
ンドリル、ベンゾフリル、ジベンゾフリル、ジベンゾジ
オキシニル、ベンゾチエニル、ジベンゾチエニル、カル
バゾリル、キサンテニル、フェナントリジニル、ジベン
ゾオキサピニル、ジベンゾチエピニル、シンノリル、ク
ロメニル、ベンゾイミダゾリルまたはヒドロベンゾチエ
ピニルである化合物もしくはその塩またはそれらの水和
物が挙げられる。
て、X1およびX2が単結合であり、X3がイソオキサゾリ
ル、チアジアゾリル、イソチアゾリル、モルホリル、イ
ンドリル、ベンゾフリル、ジベンゾフリル、ジベンゾジ
オキシニル、ベンゾチエニル、ジベンゾチエニル、カル
バゾリル、キサンテニル、フェナントリジニル、ジベン
ゾオキサピニル、ジベンゾチエピニル、シンノリル、ク
ロメニル、ベンゾイミダゾリルまたはヒドロベンゾチエ
ピニルである化合物もしくはその塩またはそれらの水和
物が挙げられる。
同様に、式(I a)で示される化合物において、X1が
単結合、X2がフェニレン、X3がアルケニル、アルキニ
ル、−CH=NR6または−N=C(R7)R8を表わす化合物
もしくはその塩またはそれらの水和物が挙げられる。
単結合、X2がフェニレン、X3がアルケニル、アルキニ
ル、−CH=NR6または−N=C(R7)R8を表わす化合物
もしくはその塩またはそれらの水和物が挙げられる。
同様に、式(I a)で示される化合物において、RがC
OOR1、X1がフェニレンまたはチオフェンジイル、X2が単
結合、−N=N−、−CH=CH−、−CONH−、−NHCO−ま
たはエチニレンおよびX3がフェニル、チアゾリニリデン
メチル、チアゾリジニリデンメチルまたはチエニルを表
わす化合物もしくはその塩またはそれらの水和物が挙げ
られる。
OOR1、X1がフェニレンまたはチオフェンジイル、X2が単
結合、−N=N−、−CH=CH−、−CONH−、−NHCO−ま
たはエチニレンおよびX3がフェニル、チアゾリニリデン
メチル、チアゾリジニリデンメチルまたはチエニルを表
わす化合物もしくはその塩またはそれらの水和物が挙げ
られる。
更に具体的には、式(I b)で示される化合物におい
て、 を表わす化合物もしくはその塩またはそれらの水和物が
挙げられる。さらに好ましい態様としては、式(I b)
で示される化合物において、RがCOOR1(R1は前記と同
意義である)で示される化合物もしくはその塩またはそ
れらの水和物が挙げられる。
て、 を表わす化合物もしくはその塩またはそれらの水和物が
挙げられる。さらに好ましい態様としては、式(I b)
で示される化合物において、RがCOOR1(R1は前記と同
意義である)で示される化合物もしくはその塩またはそ
れらの水和物が挙げられる。
同様に、式(I b)で示される化合物において、X1が
フェニレンまたはチオフェンジイル、X2が単結合、−N
=N−、−CH=CH−、エチニレン、−O−、−S−、−
CO−、−CON(R55)−(R55は前記と同意義である)、
−N(R51)CO−(R51は前記と同意義である)およびX3
がフェニルである化合物もしくはその塩またはそれらの
水和物が挙げられる。
フェニレンまたはチオフェンジイル、X2が単結合、−N
=N−、−CH=CH−、エチニレン、−O−、−S−、−
CO−、−CON(R55)−(R55は前記と同意義である)、
−N(R51)CO−(R51は前記と同意義である)およびX3
がフェニルである化合物もしくはその塩またはそれらの
水和物が挙げられる。
更に、具体的には、式(I b)で示される化合物にお
いて、 を表わす化合物もしくはその塩またはそれらの水和物が
挙げられる。さらに好ましい態様としては、Bが水素、
X1およびX2がともに単結合であり、X3がチエニル、チア
ゾリル、チアジアゾリル、イソチアゾリル、ピロリル、
ピリジル、ベンゾフリル、ベンゾイミダゾリル、ベンゾ
チエニル、ジベンゾフリル、ジベンゾチエニル、キノリ
ルまたはインドリルである化合物またはその塩が挙げら
れる。同様に、X1がフェニレン、チオフェンジイル、イ
ンドールジイルまたはオキサゾールジイル、X2が単結
合、−N=CN−、−CH=N−、エチニル、−S−または
−O−、およびX3がアリールまたはヘテロ環である化合
物もしくはその塩またはそれらの水和物が挙げられる。
いて、 を表わす化合物もしくはその塩またはそれらの水和物が
挙げられる。さらに好ましい態様としては、Bが水素、
X1およびX2がともに単結合であり、X3がチエニル、チア
ゾリル、チアジアゾリル、イソチアゾリル、ピロリル、
ピリジル、ベンゾフリル、ベンゾイミダゾリル、ベンゾ
チエニル、ジベンゾフリル、ジベンゾチエニル、キノリ
ルまたはインドリルである化合物またはその塩が挙げら
れる。同様に、X1がフェニレン、チオフェンジイル、イ
ンドールジイルまたはオキサゾールジイル、X2が単結
合、−N=CN−、−CH=N−、エチニル、−S−または
−O−、およびX3がアリールまたはヘテロ環である化合
物もしくはその塩またはそれらの水和物が挙げられる。
尚、上記一般式(I a)および(I b)で示される化合
物は本発明者らにより合成された新規化合物である。
物は本発明者らにより合成された新規化合物である。
本明細書において用いる各種語句の定義は、以下の通
りである。
りである。
「アルキレン」とは、C1〜C9は直鎖状又は分枝状のア
ルキレンを意味し、例えば、メチレン、メチルメチレ
ン、ジメチルメチレン、メチルエチルメチレン、エチレ
ン、トリメチレン、テトラメチレン、ペンタメチレン、
ヘキサメチレン、ヘプタメチレン、オクタメチレンまた
はナノメチレン等が挙げられる。上記アルキレンは、ヘ
テロ原子(酸素原子、硫黄原子または窒素原子等)もし
くはフェニレン(例えば、1,4−フェニレン、1,3−フェ
ニレン、1,2−フェニレン等)を介在していてもよく、
オキソ基を有してもよく、および/または二重結合また
は三重結合を鎖上に1個又はそれ以上、任意の位置に含
んでいてもよい。例えば、−(CH2)2−O−CH2−、−
(CH2)2−O−(CH2)2−、−(CH2)2−O−(C
H2)3−、−(CH2)2−O−(CH2)4−、−(CH2)
2−O−(CH2)5−、−(CH2)2−O−(CH2)
6−、−(CH2)2−S−(CH2)2−、−(CH2)3−
S−(CH2)2−、−CH2−S−CH2−、−CH2−S−(CH
2)4−、−CH2−N(CH3)−CH2−、−CH2−NH−(C
H2)2−、−(CH2)2−N(CH2CH3)−(CH2)3−、
−(CH2)2−1,4−フェニレン−CH2−、−(CH2)2−
O−1,3−フェニレン−CH2−、−(CH2)2−O−1,2−
フェニレン−CH2−、−(CH2)2−O−1,4−フェニレ
ン−CH2−、−CH=CH−S−CH2−1,4−フェニレン−CH2
−、−CH=CH−S−1,3−フェニレン−(CH2)2−、2
−オキソプロピレン、3−オキソペンチレン、5−オキ
ソヘキシレン、ビニレン、1−プロペニレン、2−プロ
ペニレン、1−ブテニレン、2−ブテニレン、3−ブテ
ニレン、1,2−ブタジエニレン、1,3−ブタジエニレン、
1−ペンテニレン、2−ペンテニレン、3−ペンテニレ
ン、4−ペンテニレン、1,2−ペンタジエニレン、1,3−
ペンタジエニレン、1,4−ペンタジエニレン、2,3−ペン
タジエニレン、1,4−ペンタジエニレン、1−ヘキセニ
レン、2−ヘキセニレン、3−ヘキセニレン、4−ヘキ
セニレン、5−ヘキセニレン、1,2−ヘキサジエニレ
ン、1,3−ヘキサジエニレン、1,4−ヘキサジエニレン、
1,5−ヘキサジエニレン、2,3−ヘキサジエニレン、2,4
−ヘキサジエニレン、2,5−ヘキサジエニレン、3,4−ヘ
キサジエニレン、3,5−ヘキサジエニレン、4,5−ヘキサ
ジエニレン、1,1−ジメチル−4−ヘキセニレン、1−
ヘプテニレン、2−ヘプテニレン、3−ヘプテニレン、
4−ヘプテニレン、5−ヘプテニレン、2,2−ジメチル
−5−ヘプテニレン、6−ヘプテニレン、1,2−ヘプタ
ジエニレン、1,3−ヘプタジエニレン、1,4−ヘプタジエ
ニレン、1,5−ヘプタジエニレン、1,6−ヘプタジエニレ
ン、2,3−ヘプタジエニレン、2,4−ヘプタジエニレン、
2,5−ヘプタジエニレン、2,6−ヘプタジエニレン、3,4
−ヘプタジエニレン、3,5−ヘプタジエニレン、3,6−ヘ
プタジエニレン、4,5−ヘプタジエニレン、4,6−ヘプタ
ジエニレン又は5,6−ヘプタジエニレン、1−プロピニ
レン、3−ブチニレン、2−ペンチニレン、5−ヘキシ
ニレン、6−ヘプチニレン、−(CH2)−CH=CH−O−
(CH2)2−、−CH2−S−(CH2)3−、−CH2−シス−
CH=CH−1,2−フェニレン−CH2−、−CH=CH−1,4−フ
ェニレン−(CH2)2−、−4−オキソ−4,5−ヘキセニ
レン−等が挙げられる。
ルキレンを意味し、例えば、メチレン、メチルメチレ
ン、ジメチルメチレン、メチルエチルメチレン、エチレ
ン、トリメチレン、テトラメチレン、ペンタメチレン、
ヘキサメチレン、ヘプタメチレン、オクタメチレンまた
はナノメチレン等が挙げられる。上記アルキレンは、ヘ
テロ原子(酸素原子、硫黄原子または窒素原子等)もし
くはフェニレン(例えば、1,4−フェニレン、1,3−フェ
ニレン、1,2−フェニレン等)を介在していてもよく、
オキソ基を有してもよく、および/または二重結合また
は三重結合を鎖上に1個又はそれ以上、任意の位置に含
んでいてもよい。例えば、−(CH2)2−O−CH2−、−
(CH2)2−O−(CH2)2−、−(CH2)2−O−(C
H2)3−、−(CH2)2−O−(CH2)4−、−(CH2)
2−O−(CH2)5−、−(CH2)2−O−(CH2)
6−、−(CH2)2−S−(CH2)2−、−(CH2)3−
S−(CH2)2−、−CH2−S−CH2−、−CH2−S−(CH
2)4−、−CH2−N(CH3)−CH2−、−CH2−NH−(C
H2)2−、−(CH2)2−N(CH2CH3)−(CH2)3−、
−(CH2)2−1,4−フェニレン−CH2−、−(CH2)2−
O−1,3−フェニレン−CH2−、−(CH2)2−O−1,2−
フェニレン−CH2−、−(CH2)2−O−1,4−フェニレ
ン−CH2−、−CH=CH−S−CH2−1,4−フェニレン−CH2
−、−CH=CH−S−1,3−フェニレン−(CH2)2−、2
−オキソプロピレン、3−オキソペンチレン、5−オキ
ソヘキシレン、ビニレン、1−プロペニレン、2−プロ
ペニレン、1−ブテニレン、2−ブテニレン、3−ブテ
ニレン、1,2−ブタジエニレン、1,3−ブタジエニレン、
1−ペンテニレン、2−ペンテニレン、3−ペンテニレ
ン、4−ペンテニレン、1,2−ペンタジエニレン、1,3−
ペンタジエニレン、1,4−ペンタジエニレン、2,3−ペン
タジエニレン、1,4−ペンタジエニレン、1−ヘキセニ
レン、2−ヘキセニレン、3−ヘキセニレン、4−ヘキ
セニレン、5−ヘキセニレン、1,2−ヘキサジエニレ
ン、1,3−ヘキサジエニレン、1,4−ヘキサジエニレン、
1,5−ヘキサジエニレン、2,3−ヘキサジエニレン、2,4
−ヘキサジエニレン、2,5−ヘキサジエニレン、3,4−ヘ
キサジエニレン、3,5−ヘキサジエニレン、4,5−ヘキサ
ジエニレン、1,1−ジメチル−4−ヘキセニレン、1−
ヘプテニレン、2−ヘプテニレン、3−ヘプテニレン、
4−ヘプテニレン、5−ヘプテニレン、2,2−ジメチル
−5−ヘプテニレン、6−ヘプテニレン、1,2−ヘプタ
ジエニレン、1,3−ヘプタジエニレン、1,4−ヘプタジエ
ニレン、1,5−ヘプタジエニレン、1,6−ヘプタジエニレ
ン、2,3−ヘプタジエニレン、2,4−ヘプタジエニレン、
2,5−ヘプタジエニレン、2,6−ヘプタジエニレン、3,4
−ヘプタジエニレン、3,5−ヘプタジエニレン、3,6−ヘ
プタジエニレン、4,5−ヘプタジエニレン、4,6−ヘプタ
ジエニレン又は5,6−ヘプタジエニレン、1−プロピニ
レン、3−ブチニレン、2−ペンチニレン、5−ヘキシ
ニレン、6−ヘプチニレン、−(CH2)−CH=CH−O−
(CH2)2−、−CH2−S−(CH2)3−、−CH2−シス−
CH=CH−1,2−フェニレン−CH2−、−CH=CH−1,4−フ
ェニレン−(CH2)2−、−4−オキソ−4,5−ヘキセニ
レン−等が挙げられる。
「アルキル」とは、C1〜C20の直鎖状又は分枝状のア
ルキルを意味し、例えば、メチル、エチル、n−プロピ
ル、i−プロピル、n−ブチル、i−ブチル、s−ブチ
ル、t−ブチル、n−ペンチル、i−ペンチル、ネオペ
ンチル、t−ペンチル、ヘキシル、ヘプチル、オクチ
ル、ノニル、デシル、ウンデシル、ドデシル、トリデシ
ル、テトラデシル、ペンタデシル、ヘキサデシル、ヘプ
タデシル、オクタデシル、ノナデシル、イコシル等が挙
げられる。
ルキルを意味し、例えば、メチル、エチル、n−プロピ
ル、i−プロピル、n−ブチル、i−ブチル、s−ブチ
ル、t−ブチル、n−ペンチル、i−ペンチル、ネオペ
ンチル、t−ペンチル、ヘキシル、ヘプチル、オクチ
ル、ノニル、デシル、ウンデシル、ドデシル、トリデシ
ル、テトラデシル、ペンタデシル、ヘキサデシル、ヘプ
タデシル、オクタデシル、ノナデシル、イコシル等が挙
げられる。
「アリール」とは、C6〜C14の単環または縮合環を意
味し、フェニル、ナフチル(例えば、1−ナフチル、2
−ナフチル)、アンスリル(例えば、1−アンスリル、
2−アンスリル、9−アンスリル)、フェナンスリル
(例えば、2−フェナンスリル、3−フェナンスリル、
9−フェナンスリル)、フルオレニル(例えば、2−フ
ルオレニル)等が挙げられる。特に、フェニルが好まし
い。
味し、フェニル、ナフチル(例えば、1−ナフチル、2
−ナフチル)、アンスリル(例えば、1−アンスリル、
2−アンスリル、9−アンスリル)、フェナンスリル
(例えば、2−フェナンスリル、3−フェナンスリル、
9−フェナンスリル)、フルオレニル(例えば、2−フ
ルオレニル)等が挙げられる。特に、フェニルが好まし
い。
「アラルキル」とは、前記アルキル基に前記アリール
基が置換したもので、これらは置換可能な全ての位置で
結合しうる。例えば、ベンジル、フェネチル、フェニル
プロピル(例えば、3−フェニルプロピル)、ナフチル
メチル(例えば、α−ナフチルメチル)、アンスリルメ
チル(例えば、9−アンスリルメチル)、フェナンスリ
ルメチル(例えば、3−フェナンスリルメチル)等が挙
げられる。
基が置換したもので、これらは置換可能な全ての位置で
結合しうる。例えば、ベンジル、フェネチル、フェニル
プロピル(例えば、3−フェニルプロピル)、ナフチル
メチル(例えば、α−ナフチルメチル)、アンスリルメ
チル(例えば、9−アンスリルメチル)、フェナンスリ
ルメチル(例えば、3−フェナンスリルメチル)等が挙
げられる。
「アシル」とは、脂肪族カルボン酸由来のC1〜C9のア
シルを意味し、例えば、ホルミル、アセチル、プロピオ
ニル、ブチリル、バレリル等が挙げられる。
シルを意味し、例えば、ホルミル、アセチル、プロピオ
ニル、ブチリル、バレリル等が挙げられる。
「アルキルスルホニル」とは、スルホニルに上記アル
キルが置換したもので、例えば、メチルスルホニル、エ
チルスルホニル、プロピルスルホニル等が挙げられる。
キルが置換したもので、例えば、メチルスルホニル、エ
チルスルホニル、プロピルスルホニル等が挙げられる。
「アルケニル」とは、上記アルキルに1個又はそれ以
上の二重結合を有する直鎖または分岐状のC2〜C20アル
ケニルを意味し、例えば、ビニル、1−プロペニル、2
−プロペニル、1−ブテニル、2−ブテニル、3−ブテ
ニル、1,2−ブタジエニル、1−ペンテニル、1,2−ペン
タジエニル、2−ヘキセニル、1,2−ヘキサジエニル、
3−ヘプテニル、1,5−ヘプタジエニル等が挙げられ
る。
上の二重結合を有する直鎖または分岐状のC2〜C20アル
ケニルを意味し、例えば、ビニル、1−プロペニル、2
−プロペニル、1−ブテニル、2−ブテニル、3−ブテ
ニル、1,2−ブタジエニル、1−ペンテニル、1,2−ペン
タジエニル、2−ヘキセニル、1,2−ヘキサジエニル、
3−ヘプテニル、1,5−ヘプタジエニル等が挙げられ
る。
「アルキニル」とは、上記アルキルに1個又はそれ以
上の三重結合を有する直鎖または分岐状のC2〜C20アル
キニルを意味し、例えば、エチニル、1−プロピニル、
2−プロピニル、1−ブチニル、2−ブチニル、3−ブ
チニル等が挙げられる。
上の三重結合を有する直鎖または分岐状のC2〜C20アル
キニルを意味し、例えば、エチニル、1−プロピニル、
2−プロピニル、1−ブチニル、2−ブチニル、3−ブ
チニル等が挙げられる。
「ヘテロ環」とは、任意に選ばれる、酸素原子、硫黄
原子および/または窒素原子を環内に1個以上含み、か
つ炭素環もしくは他のヘテロ環と縮合していてもよい5
〜7員の環を意味し、これらは置換可能な任意の位置で
結合しうる。例えば、ピロリル(例えば、1−ピロリ
ル、3−ピロリル)、インドリル(例えば、2−インド
リル、3−インドリル、6−インドリル)、カルバゾリ
ル(例えば、2−カルバゾリル、3−カルバゾリル)、
イミダゾリル(例えば、1−イミダゾリル、4−イミダ
ゾリル)、ピラゾリル(例えば、1−ピラゾリル、3−
ピラゾリル)、ベンゾイミダゾリル(例えば、2−ベン
ゾイミダゾリル、5−ベンゾイミダゾリル)、インダゾ
リル(例えば、3−インダゾリル)、インドリジニル
(例えば、6−インドリジニル)、ピリジル(例えば、
2−ピリジル、3−ピリジル、4−ピリジル)、キノリ
ル(例えば、8−キノリル)、イソキノリル(例えば、
3−イソキノリル)、アクリジル(例えば、1−アクリ
ジル)、フェナンスリジニル(例えば、2−フェナンス
リジニル、3−フェナンスルジニル)、ピリダジニル
(例えば、3−ピリダジニル)、ピリミジニル(例え
ば、4−ピリミジニル)、ピラジニル(例えば、2−ピ
ラジニル)、シンノリニル(例えば、3−シンノリニ
ル)、フタラジニル(例えば、5−フタラジニル)、キ
ナゾリニル(例えば、2−キナゾリニル)、イソオキサ
ゾリル(例えば、3−イソオキサゾリル、4−イソオキ
サゾリル)、ベンゾイソオキサゾリル(例えば、1,2−
ベンゾイソオキサゾール−4−イル、2,1−ベンゾイソ
オキサゾール−3−イル)、オキサゾリル(例えば、2
−オキサゾリル、4−オキサゾリル、5−オキサゾリ
ル)、ベンゾオキサゾリル(例えば、2−ベンゾオキサ
ゾリル)、ベンゾオキサジアゾリル(例えば、4−ベン
ゾオキサジアゾリル)、イソチアゾリル(例えば、3−
イソチアゾリル、4−イソチアゾリル)、ベンゾイソチ
アゾリル(例えば、1,2−ベンゾイソチアゾール−3−
イル、2,1−ベンゾイソチアゾール−5−イル)、チア
ゾリル(例えば、2−チアゾリル)、ベンゾチアゾリル
(例えば、2−ベンゾチアゾリル)、チアジアゾリル
(例えば、1,2,3−チアジアゾール−4−イル)、オキ
サジアゾリル(例えば、1,3,4−オキサジアゾール−2
−イル)、ジヒドロオキサジアゾリル(例えば、4,5−
ジヒドロ−1,2,4−オキサジアゾール−3−イル)、フ
リル(例えば、2−フリル、3−フリル)、ベンゾフリ
ル(例えば、3−ベンゾフリル)、イソベンゾフリル
(例えば、1−イソベンゾフリル)、チエニル(例え
ば、2−チエニル、3−チエニル)、ベンゾチエニル
(例えば、1−ベンゾチオフェン−2−イル、2−ベン
ゾチオフェン−1−イル)、テトラゾリル(例えば、5
−テトラゾリル)、ベンゾジオキソリル(例えば、1,3
−ベンゾジオキソール−5−イル)、ジベンゾフリル
(例えば、2−ジベンゾフリル、3−ジベンゾフリ
ル)、ジベンゾオキセピニル(例えば、ジベンゾ[b,
f]オキセピン−2−イル)、ジヒドロジベンゾオキセ
ピニル(例えば、ジヒドロジベンゾ[b,f]オキセピン
−2−イル)、クロメニル(例えば、2H−クロメン−3
−イル、4H−クロメン−2−イル)、ジベンゾチエピニ
ル(例えば、ジベンゾ[b,f]チエピン−3−イル、ジ
ヒドロジベンゾ[b,f]チエピン−3−イル)、モリホ
リニル(例えば、1,4−モルホリン−4−イル)、フェ
ノチアジニル(例えば、2−フェノチアジニル)、シク
ロペンタチエニル(例えば、シクロペンタ[b]チオフ
ェン−3−イル)、シクロヘキサチエニル(例えば、シ
クロヘキサ[b]チオフェン−3−イル)、シクロヘプ
タチエニル(例えば、シクロヘプタ[b]チオフェン−
3−イル)、ジベンゾチエニル(例えば、2−ジベンゾ
チエニル)、ジベンゾピラニル(例えば、2−ジベンゾ
ピラニル)、ジベンゾ−p−ジオキシル(例えば、2−
ジベンゾ−p−ジオキシル)等が挙げられる。
原子および/または窒素原子を環内に1個以上含み、か
つ炭素環もしくは他のヘテロ環と縮合していてもよい5
〜7員の環を意味し、これらは置換可能な任意の位置で
結合しうる。例えば、ピロリル(例えば、1−ピロリ
ル、3−ピロリル)、インドリル(例えば、2−インド
リル、3−インドリル、6−インドリル)、カルバゾリ
ル(例えば、2−カルバゾリル、3−カルバゾリル)、
イミダゾリル(例えば、1−イミダゾリル、4−イミダ
ゾリル)、ピラゾリル(例えば、1−ピラゾリル、3−
ピラゾリル)、ベンゾイミダゾリル(例えば、2−ベン
ゾイミダゾリル、5−ベンゾイミダゾリル)、インダゾ
リル(例えば、3−インダゾリル)、インドリジニル
(例えば、6−インドリジニル)、ピリジル(例えば、
2−ピリジル、3−ピリジル、4−ピリジル)、キノリ
ル(例えば、8−キノリル)、イソキノリル(例えば、
3−イソキノリル)、アクリジル(例えば、1−アクリ
ジル)、フェナンスリジニル(例えば、2−フェナンス
リジニル、3−フェナンスルジニル)、ピリダジニル
(例えば、3−ピリダジニル)、ピリミジニル(例え
ば、4−ピリミジニル)、ピラジニル(例えば、2−ピ
ラジニル)、シンノリニル(例えば、3−シンノリニ
ル)、フタラジニル(例えば、5−フタラジニル)、キ
ナゾリニル(例えば、2−キナゾリニル)、イソオキサ
ゾリル(例えば、3−イソオキサゾリル、4−イソオキ
サゾリル)、ベンゾイソオキサゾリル(例えば、1,2−
ベンゾイソオキサゾール−4−イル、2,1−ベンゾイソ
オキサゾール−3−イル)、オキサゾリル(例えば、2
−オキサゾリル、4−オキサゾリル、5−オキサゾリ
ル)、ベンゾオキサゾリル(例えば、2−ベンゾオキサ
ゾリル)、ベンゾオキサジアゾリル(例えば、4−ベン
ゾオキサジアゾリル)、イソチアゾリル(例えば、3−
イソチアゾリル、4−イソチアゾリル)、ベンゾイソチ
アゾリル(例えば、1,2−ベンゾイソチアゾール−3−
イル、2,1−ベンゾイソチアゾール−5−イル)、チア
ゾリル(例えば、2−チアゾリル)、ベンゾチアゾリル
(例えば、2−ベンゾチアゾリル)、チアジアゾリル
(例えば、1,2,3−チアジアゾール−4−イル)、オキ
サジアゾリル(例えば、1,3,4−オキサジアゾール−2
−イル)、ジヒドロオキサジアゾリル(例えば、4,5−
ジヒドロ−1,2,4−オキサジアゾール−3−イル)、フ
リル(例えば、2−フリル、3−フリル)、ベンゾフリ
ル(例えば、3−ベンゾフリル)、イソベンゾフリル
(例えば、1−イソベンゾフリル)、チエニル(例え
ば、2−チエニル、3−チエニル)、ベンゾチエニル
(例えば、1−ベンゾチオフェン−2−イル、2−ベン
ゾチオフェン−1−イル)、テトラゾリル(例えば、5
−テトラゾリル)、ベンゾジオキソリル(例えば、1,3
−ベンゾジオキソール−5−イル)、ジベンゾフリル
(例えば、2−ジベンゾフリル、3−ジベンゾフリ
ル)、ジベンゾオキセピニル(例えば、ジベンゾ[b,
f]オキセピン−2−イル)、ジヒドロジベンゾオキセ
ピニル(例えば、ジヒドロジベンゾ[b,f]オキセピン
−2−イル)、クロメニル(例えば、2H−クロメン−3
−イル、4H−クロメン−2−イル)、ジベンゾチエピニ
ル(例えば、ジベンゾ[b,f]チエピン−3−イル、ジ
ヒドロジベンゾ[b,f]チエピン−3−イル)、モリホ
リニル(例えば、1,4−モルホリン−4−イル)、フェ
ノチアジニル(例えば、2−フェノチアジニル)、シク
ロペンタチエニル(例えば、シクロペンタ[b]チオフ
ェン−3−イル)、シクロヘキサチエニル(例えば、シ
クロヘキサ[b]チオフェン−3−イル)、シクロヘプ
タチエニル(例えば、シクロヘプタ[b]チオフェン−
3−イル)、ジベンゾチエニル(例えば、2−ジベンゾ
チエニル)、ジベンゾピラニル(例えば、2−ジベンゾ
ピラニル)、ジベンゾ−p−ジオキシル(例えば、2−
ジベンゾ−p−ジオキシル)等が挙げられる。
「シクロアルキル」とは、C3〜C8の環状アルキルを意
味し、例えば、シクロプロピル、シクロブチル、シルロ
ペンチル、シクロヘキシル等が挙げられる。
味し、例えば、シクロプロピル、シクロブチル、シルロ
ペンチル、シクロヘキシル等が挙げられる。
「シクロアルケニル」とは、C3〜C8の環状アルケニル
を意味し、例えば、シクロプロペニル(例えば、1−シ
クロプロペニル)、シクロブテニル(例えば、2−シク
ロブテン−1−イル)、シクロペンテニル(例えば、1
−シクロペンテン−1−イル)、シクロヘキセニル(例
えば、1−シクロヘキセン−1−イル)等が挙げられ
る。
を意味し、例えば、シクロプロペニル(例えば、1−シ
クロプロペニル)、シクロブテニル(例えば、2−シク
ロブテン−1−イル)、シクロペンテニル(例えば、1
−シクロペンテン−1−イル)、シクロヘキセニル(例
えば、1−シクロヘキセン−1−イル)等が挙げられ
る。
「アルコキシ」とは、C1〜C6のアルコキシを意味し、
例えば、メトキシ、エトキシ、n−プロポキシ、i−プ
ロポキシ、n−ブトキシ等が挙げられる。
例えば、メトキシ、エトキシ、n−プロポキシ、i−プ
ロポキシ、n−ブトキシ等が挙げられる。
「置換もしくは非置換アミノ」における置換アミノと
は、例えば、メチルアミノ、エチルアミノ、ジメチルア
ミノ、シクロヘキシルアミノ、フェニルアミノ、ジフェ
ニルアミノ等のモノ−もしくはジ−置換アミノ、ピペリ
ジノ、ピペラジノ、モルホリノ等の環状アミノが挙げら
れる。
は、例えば、メチルアミノ、エチルアミノ、ジメチルア
ミノ、シクロヘキシルアミノ、フェニルアミノ、ジフェ
ニルアミノ等のモノ−もしくはジ−置換アミノ、ピペリ
ジノ、ピペラジノ、モルホリノ等の環状アミノが挙げら
れる。
「アシルオキシ」とは、前記の「アシル」から誘導さ
れるアシルオキシを意味し、例えば、アセチルオキシ、
プロピオニルオキシ、ブチリルオキシ、バレリルオキシ
等が挙げられる。
れるアシルオキシを意味し、例えば、アセチルオキシ、
プロピオニルオキシ、ブチリルオキシ、バレリルオキシ
等が挙げられる。
「ハロゲン」とは、フッ素、塩素、臭素、ヨウ素を意
味する。
味する。
「アルコキシカルボニル」とは、前記の「アルコキ
シ」から誘導されるアルコキシカルボニルを意味し、例
えば、メトキシカルボニル、エトキシカルボニル、フェ
ニルオキシカルボニル等が挙げられる。
シ」から誘導されるアルコキシカルボニルを意味し、例
えば、メトキシカルボニル、エトキシカルボニル、フェ
ニルオキシカルボニル等が挙げられる。
「アラルキルオキシカルボニル」とは、前記の「アラ
ルキル」から誘導されるアラルキルオキシカルボニルを
意味し、例えば、ベンジルオキシカルボニル、フェネチ
ルオキシカルボニル等が挙げられる。
ルキル」から誘導されるアラルキルオキシカルボニルを
意味し、例えば、ベンジルオキシカルボニル、フェネチ
ルオキシカルボニル等が挙げられる。
「アリールオキシカルボニル」とは、前記の「アリー
ル」から、誘導されるアリールオキシカルボニルを意味
し、例えば、フェニルオキシカルボニル、ナフチルオキ
シカルボニル等が挙げられる。
ル」から、誘導されるアリールオキシカルボニルを意味
し、例えば、フェニルオキシカルボニル、ナフチルオキ
シカルボニル等が挙げられる。
「アルケニルオキシ」とは、前記の「アルケニル」か
ら、誘導されるアルケニルオキシを意味し、例えば、ビ
ニルオキシ、1−プロペニルオキシ、2−ブテニルオキ
シ等が挙げられる。
ら、誘導されるアルケニルオキシを意味し、例えば、ビ
ニルオキシ、1−プロペニルオキシ、2−ブテニルオキ
シ等が挙げられる。
「ヒドロキシアルキル」とは、前記の「アルキル」か
ら、誘導されるヒドロキシアルキルを意味し、例えば、
ヒドロキシメチル、ヒドロキシエチル、ヒドロキシプロ
ピル等が挙げられる。
ら、誘導されるヒドロキシアルキルを意味し、例えば、
ヒドロキシメチル、ヒドロキシエチル、ヒドロキシプロ
ピル等が挙げられる。
「アルキルチオ」とは、前記の「アルキル」から、誘
導されるアルキルチオを意味し、例えば、メチルチオ、
エチルチオ、プロピルチオ等が挙げられる。
導されるアルキルチオを意味し、例えば、メチルチオ、
エチルチオ、プロピルチオ等が挙げられる。
「アルキレンジオキシ」とは、C1〜C3、例えば、メチ
レンジオキシ、エチレンジオキシ、プロピレンジオキシ
等が挙げられる。
レンジオキシ、エチレンジオキシ、プロピレンジオキシ
等が挙げられる。
「フェニレン」、「ナフチレン」、「チオフェンジイ
ル」、「インドールジイル」、「オキサゾールジイ
ル」、「オキサジアゾールジイル」、「テトラゾールジ
イル」においては、置換可能な任意の2箇所で、隣接す
る基と結合しうる。
ル」、「インドールジイル」、「オキサゾールジイ
ル」、「オキサジアゾールジイル」、「テトラゾールジ
イル」においては、置換可能な任意の2箇所で、隣接す
る基と結合しうる。
また、前記の定義において、置換基が環状のものは、
ニトロ、アルコキシ、スルファモイル、置換もしくは非
置換アミノ、アシル、アシルオキシ、ヒドロキシ、ハロ
ゲン、アルキル、アルキニル、カルボキシ、アルコキシ
カルボニル、アラルキルオキシカルボニル、アリールオ
キシカルボニル、メシルオキシ、シアノ、アルケニルオ
キシ、ヒドロキシアルキル、トリフルオロメチル、アル
キルチオ、−N=PPh3、オキソ、チオキソ、ヒドロキシ
イミノ、アルコキシイミノ、フェニルおよびアルキレン
ジオキシから選ばれる1〜3個の基で置換されていても
よいが、環上におけるそれらの置換基は、置換可能な任
意の位置で置換していてもよい。
ニトロ、アルコキシ、スルファモイル、置換もしくは非
置換アミノ、アシル、アシルオキシ、ヒドロキシ、ハロ
ゲン、アルキル、アルキニル、カルボキシ、アルコキシ
カルボニル、アラルキルオキシカルボニル、アリールオ
キシカルボニル、メシルオキシ、シアノ、アルケニルオ
キシ、ヒドロキシアルキル、トリフルオロメチル、アル
キルチオ、−N=PPh3、オキソ、チオキソ、ヒドロキシ
イミノ、アルコキシイミノ、フェニルおよびアルキレン
ジオキシから選ばれる1〜3個の基で置換されていても
よいが、環上におけるそれらの置換基は、置換可能な任
意の位置で置換していてもよい。
一般式(I)の化合物の塩としては、アルカリ金属塩
(例えば、リチウム塩、ナトリウム塩もしくはカリウム
塩等)、アルカリ土類金属塩、(例えば、カルシウム塩
等)、有機塩基(例えば、トロメタミン、トリメチルア
ミン、トリエチルアミン、2−アミノブタン、t−ブチ
ルアミン、ジイソプロピルエチルアミン、n−ブチルメ
チルアミシクロヘキシルアミン、ジシクロヘキシルアミ
ン、N−イソプロピルシクロヘキシルアミン、フルフリ
ルアミン、ベンジルアミン、メチルベンジルアミン、ジ
ベンジルアミン、N,N−ジメチルベンジルアミン、2−
クロロベンジルアミン、4−メトキシベンジルアミン、
1−ナフチレンメチルアミン、ジフェニルベンジルアミ
ン、トリフェニルアミン、1−ナフチルアミン、1−ア
ミノアントラセン、2−アミノアントラセン、デヒドロ
アピエチルアミン、N−メチルモリホリンもしくはピリ
ジン)との塩、またはアミノ酸塩(例えば、リジン塩も
しくはアルギニン塩等)を挙げることができる。
(例えば、リチウム塩、ナトリウム塩もしくはカリウム
塩等)、アルカリ土類金属塩、(例えば、カルシウム塩
等)、有機塩基(例えば、トロメタミン、トリメチルア
ミン、トリエチルアミン、2−アミノブタン、t−ブチ
ルアミン、ジイソプロピルエチルアミン、n−ブチルメ
チルアミシクロヘキシルアミン、ジシクロヘキシルアミ
ン、N−イソプロピルシクロヘキシルアミン、フルフリ
ルアミン、ベンジルアミン、メチルベンジルアミン、ジ
ベンジルアミン、N,N−ジメチルベンジルアミン、2−
クロロベンジルアミン、4−メトキシベンジルアミン、
1−ナフチレンメチルアミン、ジフェニルベンジルアミ
ン、トリフェニルアミン、1−ナフチルアミン、1−ア
ミノアントラセン、2−アミノアントラセン、デヒドロ
アピエチルアミン、N−メチルモリホリンもしくはピリ
ジン)との塩、またはアミノ酸塩(例えば、リジン塩も
しくはアルギニン塩等)を挙げることができる。
水和物とは、式(I)で示される化合物またはその塩
の水和物を意味し、例えば、1水和物、2水和物を挙げ
ることができる。
の水和物を意味し、例えば、1水和物、2水和物を挙げ
ることができる。
本発明化合物は、一般式(I)で示され、その全ての
立体異方性(ジアステレオマー、エピマー、エナンチオ
マーなど)又はラセミ体を含む。
立体異方性(ジアステレオマー、エピマー、エナンチオ
マーなど)又はラセミ体を含む。
一般式(I)で示される化合物の中、m=1の化合
物、とくに、後記の表3bおよび3cに示した化合物は、特
開平2−180862明細書に記載された公知化合物である。
物、とくに、後記の表3bおよび3cに示した化合物は、特
開平2−180862明細書に記載された公知化合物である。
一般式(I)で示される化合物の中、m=0の化合物
[一般式(I′)で示される化合物]は、下記反応式で
示されるごとく、一般式(II)で示されるアミノ化合物
に部分構造式Z−X1−X2−X3に対応するスルホン酸また
はカルボン酸の反応性誘導体を反応させることにより製
造することができる。
[一般式(I′)で示される化合物]は、下記反応式で
示されるごとく、一般式(II)で示されるアミノ化合物
に部分構造式Z−X1−X2−X3に対応するスルホン酸また
はカルボン酸の反応性誘導体を反応させることにより製
造することができる。
(式中、A、B、R、X1、X2、X3、YおよびZは前記と
同意義である。) 部分構造式Z−X1−X2−X3に対応するスルホン酸は一
般式X3−X2−X1−SO2OHで表される化合物であり、ま
た、カルボン酸とはX3−X2−X1−COOHで表される化合物
を意味する。これらスルホン酸またはカルボン酸の反応
性誘導体とは、対応する酸ハロゲン化物(例えば、塩化
物、臭化物、沃化物)、酸無水物(例えば、ぎ酸もしく
は酢酸との混合酸無水物)、活性エステル(例えば、ス
クシンイミドエステル)などを意味し、通常アミノ基の
アシル化に使用するアシル化剤を包含する。また、カル
ボン酸X3−X2−X1−COOHは反応性誘導体とはせずに、ア
ミンとカルボン酸の縮合反応に使用する縮合剤(例え
ば、ジシクロヘキシルカルボジイミド(DCC)、1−エ
チル−3−(3−ジメチルアミノプロピル)カルボジイ
ミド、N,N′−カルボニルジイミダゾール)の存在下に
反応させてもよい。
同意義である。) 部分構造式Z−X1−X2−X3に対応するスルホン酸は一
般式X3−X2−X1−SO2OHで表される化合物であり、ま
た、カルボン酸とはX3−X2−X1−COOHで表される化合物
を意味する。これらスルホン酸またはカルボン酸の反応
性誘導体とは、対応する酸ハロゲン化物(例えば、塩化
物、臭化物、沃化物)、酸無水物(例えば、ぎ酸もしく
は酢酸との混合酸無水物)、活性エステル(例えば、ス
クシンイミドエステル)などを意味し、通常アミノ基の
アシル化に使用するアシル化剤を包含する。また、カル
ボン酸X3−X2−X1−COOHは反応性誘導体とはせずに、ア
ミンとカルボン酸の縮合反応に使用する縮合剤(例え
ば、ジシクロヘキシルカルボジイミド(DCC)、1−エ
チル−3−(3−ジメチルアミノプロピル)カルボジイ
ミド、N,N′−カルボニルジイミダゾール)の存在下に
反応させてもよい。
反応は通常のアミノ基のアシル化反応の条件に従って
行えばよく、例えば、酸ハロゲン化物による縮合反応の
場合、溶媒としてエーテル系溶媒(例えば、ジエチルエ
ーテル、テトラヒドロフラン、ジオキサン)、ベンゼン
系溶媒(例えば、ベンゼン、トルエン、キシレン)、ハ
ロゲン化炭化水素系溶媒(例えば、ジクロロメタン、ジ
クロロエタン、クロロホルム)、その他、酢酸エチル、
ジメチルホルムアミド、ジメチルスルホキシド、アセト
ニトリルなどを使用し、要すれば塩基(例えば、トリエ
チルアミン、ピリジン、N,N−ジメチルアミノピリジ
ン、N−メチルモルホリンなどの有機塩基、あるいは水
酸化ナトリウム、水酸化カリウム、炭酸カリウムなどの
無機塩基)の存在下、冷却下ないし室温あるいは加熱
下、好ましくは−20℃ないし氷冷下あるいは室温ないし
反応系の加熱還流温度で、数分ないし数十時間、好まし
くは0.5時間ないし24時間、より好ましくは1時間ない
し12時間実施すればよい。
行えばよく、例えば、酸ハロゲン化物による縮合反応の
場合、溶媒としてエーテル系溶媒(例えば、ジエチルエ
ーテル、テトラヒドロフラン、ジオキサン)、ベンゼン
系溶媒(例えば、ベンゼン、トルエン、キシレン)、ハ
ロゲン化炭化水素系溶媒(例えば、ジクロロメタン、ジ
クロロエタン、クロロホルム)、その他、酢酸エチル、
ジメチルホルムアミド、ジメチルスルホキシド、アセト
ニトリルなどを使用し、要すれば塩基(例えば、トリエ
チルアミン、ピリジン、N,N−ジメチルアミノピリジ
ン、N−メチルモルホリンなどの有機塩基、あるいは水
酸化ナトリウム、水酸化カリウム、炭酸カリウムなどの
無機塩基)の存在下、冷却下ないし室温あるいは加熱
下、好ましくは−20℃ないし氷冷下あるいは室温ないし
反応系の加熱還流温度で、数分ないし数十時間、好まし
くは0.5時間ないし24時間、より好ましくは1時間ない
し12時間実施すればよい。
他の反応性誘導体あるいは遊離の酸とアミン(II)と
の反応においても、各反応性誘導体あるいは遊離酸の性
質に応じて、公知の方法に従い、反応条件を定めればよ
い。
の反応においても、各反応性誘導体あるいは遊離酸の性
質に応じて、公知の方法に従い、反応条件を定めればよ
い。
反応生成物は通常の精製法、例えば、溶媒抽出、クロ
マトグラフィー、再結晶法などにより、精製することが
できる。
マトグラフィー、再結晶法などにより、精製することが
できる。
本反応法における原料化合物(II)の具体例を示す
と、3−アミノ[2.2.1]ビシクロ環系化合物の具体例
としては、7−(3−アミノビシクロ[2.2.1]ヘプト
−2−イル)−5−ヘプテン酸、7−(3−アミノビシ
クロ[2.2.1]ヘプト−2−イル)−2,2−ジメチル−5
−ヘプテン酸、7−(N−メチル−3−アミノビシクロ
[2.2.1]ヘプト−2−イル)−5−ヘプテン酸、6−
(3−アミノビシクロ[2.2.1]ヘプト−2−イル)−
5−ヘキセン酸等が例示される。また、2−アミノ−6,
6−ジメチル[3.1.1]ビシクロ環系化合物の具体例とし
ては、7−(2−アミノ−6,6−ジメチルビシクロ[3.
1.1]ヘプト−3−イル)−5−ヘプテン酸等が例示さ
れる。また、これら原料化合物のヘプテン酸類は飽和と
なってヘプタン酸となってもよいし、−O−、−S−、
−NH−等のヘテロ原子もしくはヘテロ基あるいはフェニ
レンが鎖の途中に介在してもよいし、オキソ基で置換さ
れていてもよく、7−(3−アミノビシクロ[2.2.1]
ヘプト−2−イル)ヘプタン酸、4−[2−(2−アミ
ノビシクロ[3.1.1]ヘプト−3−イル)エトキシフェ
ニル酢酸、7−(3−アミノビシクロ[2.2.1]ヘプト
−2−イル)−6−オキソヘプテン酸等が例示される。
これらの原料化合物は、特公平5−79060号明細書、特
公平6−23170号明細書に記載された公知化合物である
か、あるいはこれらの明細書に記載の方法に従って製造
することができる。
と、3−アミノ[2.2.1]ビシクロ環系化合物の具体例
としては、7−(3−アミノビシクロ[2.2.1]ヘプト
−2−イル)−5−ヘプテン酸、7−(3−アミノビシ
クロ[2.2.1]ヘプト−2−イル)−2,2−ジメチル−5
−ヘプテン酸、7−(N−メチル−3−アミノビシクロ
[2.2.1]ヘプト−2−イル)−5−ヘプテン酸、6−
(3−アミノビシクロ[2.2.1]ヘプト−2−イル)−
5−ヘキセン酸等が例示される。また、2−アミノ−6,
6−ジメチル[3.1.1]ビシクロ環系化合物の具体例とし
ては、7−(2−アミノ−6,6−ジメチルビシクロ[3.
1.1]ヘプト−3−イル)−5−ヘプテン酸等が例示さ
れる。また、これら原料化合物のヘプテン酸類は飽和と
なってヘプタン酸となってもよいし、−O−、−S−、
−NH−等のヘテロ原子もしくはヘテロ基あるいはフェニ
レンが鎖の途中に介在してもよいし、オキソ基で置換さ
れていてもよく、7−(3−アミノビシクロ[2.2.1]
ヘプト−2−イル)ヘプタン酸、4−[2−(2−アミ
ノビシクロ[3.1.1]ヘプト−3−イル)エトキシフェ
ニル酢酸、7−(3−アミノビシクロ[2.2.1]ヘプト
−2−イル)−6−オキソヘプテン酸等が例示される。
これらの原料化合物は、特公平5−79060号明細書、特
公平6−23170号明細書に記載された公知化合物である
か、あるいはこれらの明細書に記載の方法に従って製造
することができる。
部分構造式Z−X1−X2−X3に対応するスルホン酸X3−
X2−X1−SO2OHおよびカルボン酸X3−X2−X1−COOHと
は、前記Xに対応する置換基を有するスルホン酸または
カルボン酸、すなわち、アルカンスルホン酸またはカル
ボン酸、アルケンスルホン酸またはカルボン酸、アルキ
ルスルホン酸またはカルボン酸、シクロアルカンスルホ
ン酸またはカルボン酸、シクロアルケンスルホン酸また
はカルボン酸、アリールスルホン酸またはカルボン酸、
アラルキルオキシスルホン酸またはカルボン酸、ヘテロ
環置換スルホン酸またはカルボン酸、ヘテロアリールア
ルキルスルホン酸またはカルボン酸、および置換アミノ
スルホン酸またはまたはカルボン酸である。これらのス
ルホン酸およびカルボン酸は、それぞれ前記定義の置換
基を有することができる。また、これらのスルホン酸お
よびカルボン酸は、市販品として入手可能であるか、あ
るいは既知の化合物から既知の方法に従って容易に合成
できるものである。反応に際し、これらのスルホン酸お
よびカルボン酸は、必要に応じて、対応する上記の反応
性誘導体とすることができる。例えば、酸ハロゲン化物
とするときは、ハロゲン化チオニル(例えば、塩化チオ
ニル、ハロゲン化リン(例えば、三塩化リン、五塩化リ
ン)、ハロゲン化オギザリル(例えば、塩化オギザリ
ル)等と公知の方法(例えば、新実験化学講座14巻1787
頁(1978);Synthesis 852−854(1986);新実験化学
講座22巻115頁(1992))に従って反応させればよい。
他の反応性誘導体についても同様に公知の方法で調製す
ることができる。
X2−X1−SO2OHおよびカルボン酸X3−X2−X1−COOHと
は、前記Xに対応する置換基を有するスルホン酸または
カルボン酸、すなわち、アルカンスルホン酸またはカル
ボン酸、アルケンスルホン酸またはカルボン酸、アルキ
ルスルホン酸またはカルボン酸、シクロアルカンスルホ
ン酸またはカルボン酸、シクロアルケンスルホン酸また
はカルボン酸、アリールスルホン酸またはカルボン酸、
アラルキルオキシスルホン酸またはカルボン酸、ヘテロ
環置換スルホン酸またはカルボン酸、ヘテロアリールア
ルキルスルホン酸またはカルボン酸、および置換アミノ
スルホン酸またはまたはカルボン酸である。これらのス
ルホン酸およびカルボン酸は、それぞれ前記定義の置換
基を有することができる。また、これらのスルホン酸お
よびカルボン酸は、市販品として入手可能であるか、あ
るいは既知の化合物から既知の方法に従って容易に合成
できるものである。反応に際し、これらのスルホン酸お
よびカルボン酸は、必要に応じて、対応する上記の反応
性誘導体とすることができる。例えば、酸ハロゲン化物
とするときは、ハロゲン化チオニル(例えば、塩化チオ
ニル、ハロゲン化リン(例えば、三塩化リン、五塩化リ
ン)、ハロゲン化オギザリル(例えば、塩化オギザリ
ル)等と公知の方法(例えば、新実験化学講座14巻1787
頁(1978);Synthesis 852−854(1986);新実験化学
講座22巻115頁(1992))に従って反応させればよい。
他の反応性誘導体についても同様に公知の方法で調製す
ることができる。
本発明目的化合物(I)の中、側鎖Aが不飽和結合、
特に二重結合を有する化合物は、下記一般式(III)で
表わされるアルデヒド誘導体に、側鎖A−R部分の残余
部分に対応するイリド化合物をウィティッヒ(Wittig)
反応の条件に従って反応させ製造することもできる。
特に二重結合を有する化合物は、下記一般式(III)で
表わされるアルデヒド誘導体に、側鎖A−R部分の残余
部分に対応するイリド化合物をウィティッヒ(Wittig)
反応の条件に従って反応させ製造することもできる。
(式中、A、B、R、X1、X2、X3、YおよびZは前記と
同意義である。) 原料化合物(III)は、例えば、特開平2−256650号
明細書に記載の方法に従って製造することができる。ま
た、側鎖A−R部分の残余部分に対応するイリド化合物
は、対応するハロゲン化アルカン酸もしくはそのエステ
ル誘導体、エーテル誘導体、アミド誘導体等とトリフェ
ニルホスフィンとを塩基の存在下、公知の方法に従い反
応させ合成することができる。
同意義である。) 原料化合物(III)は、例えば、特開平2−256650号
明細書に記載の方法に従って製造することができる。ま
た、側鎖A−R部分の残余部分に対応するイリド化合物
は、対応するハロゲン化アルカン酸もしくはそのエステ
ル誘導体、エーテル誘導体、アミド誘導体等とトリフェ
ニルホスフィンとを塩基の存在下、公知の方法に従い反
応させ合成することができる。
本発明目的化合物(I)においてRがCOOHである化合
物は、所望により、対応するエステル誘導体、アルコー
ル誘導体、エーテル誘導体、アミド誘導体とすることも
できる。例えば、エステル誘導体はカルボン酸を公知の
方法に従いエステル化することにより製造することがで
きる。また、エステル誘導体を還元すればアルコール誘
導体とすることができるし、アミド化すればアミド誘導
体とすることもできる。エーテル誘導体はアルコール誘
導体をO−アルキル化することによっても製造すること
ができる。
物は、所望により、対応するエステル誘導体、アルコー
ル誘導体、エーテル誘導体、アミド誘導体とすることも
できる。例えば、エステル誘導体はカルボン酸を公知の
方法に従いエステル化することにより製造することがで
きる。また、エステル誘導体を還元すればアルコール誘
導体とすることができるし、アミド化すればアミド誘導
体とすることもできる。エーテル誘導体はアルコール誘
導体をO−アルキル化することによっても製造すること
ができる。
本発明の化合物(I)はインビトロでPGD2受容体と結
合することによるPGD2拮抗作用を示し、PGD2の生産過多
に起因する肥満細胞機能不全と関連した疾患の治療剤と
して有用である。例えば全身性肥満細胞症や全身性肥満
細胞活性化障害の治療剤、抗気管収縮剤、抗喘息剤、抗
アレルギー性鼻炎剤、抗アレルギー性結膜炎剤、抗蕁麻
疹剤、虚血再灌流傷害治療薬、抗炎症剤として用いるこ
とができる。特に、本発明化合物(I)は、インビボで
鼻閉抑制作用を示すことから、鼻閉症の治療剤として有
用である。
合することによるPGD2拮抗作用を示し、PGD2の生産過多
に起因する肥満細胞機能不全と関連した疾患の治療剤と
して有用である。例えば全身性肥満細胞症や全身性肥満
細胞活性化障害の治療剤、抗気管収縮剤、抗喘息剤、抗
アレルギー性鼻炎剤、抗アレルギー性結膜炎剤、抗蕁麻
疹剤、虚血再灌流傷害治療薬、抗炎症剤として用いるこ
とができる。特に、本発明化合物(I)は、インビボで
鼻閉抑制作用を示すことから、鼻閉症の治療剤として有
用である。
本発明の化合物(I)を治療に用いるには、通常の経
口又は非経口投与用の製剤として製剤化する。本発明の
化合物(I)を含有する医薬組成物は、経口及び非経口
投与のための剤形をとることができる。即ち、錠剤、カ
プセル剤、顆粒剤、散剤、シロップ剤などの経口投与製
剤、あるいは、静脈注射、筋肉注射、皮下注射などの注
射用溶液又は懸濁液、吸入薬、点眼薬、点鼻薬、坐剤、
もしくは軟膏剤などの経皮投与用製剤などの非経口製剤
とすることもできる。
口又は非経口投与用の製剤として製剤化する。本発明の
化合物(I)を含有する医薬組成物は、経口及び非経口
投与のための剤形をとることができる。即ち、錠剤、カ
プセル剤、顆粒剤、散剤、シロップ剤などの経口投与製
剤、あるいは、静脈注射、筋肉注射、皮下注射などの注
射用溶液又は懸濁液、吸入薬、点眼薬、点鼻薬、坐剤、
もしくは軟膏剤などの経皮投与用製剤などの非経口製剤
とすることもできる。
これらの製剤は当業者既知の適当な担体、賦形剤、溶
媒、基剤等を用いて製造することができる。例えば、錠
剤の場合、活性成分と補助成分を一緒に圧縮又は成型す
る。補助成分としては、製剤的に許容される賦形剤、例
えば結合剤(例、トウモロコシでん粉)、充填剤(例、
ラクトーク、微結晶性セルロース)、崩壊剤(例、でん
粉グリコール酸ナトリウム)又は滑沢剤(例、ステアリ
ン酸マグネシウム)などが用いられる。錠剤は、適宜、
コーティングしてもよい。シロップ剤、液剤、懸濁剤な
どの液体製剤の場合、例えば、懸濁化剤(例、メチルセ
ルロース)、乳化剤(例、レシチン)、保存剤などを用
いる。注射用製剤の場合、溶液、懸濁液又は油性もしく
は水性乳濁液の形態のいずれでもよく、これらは懸濁安
定剤又は分散剤などを含有していてもよい。吸入剤とし
て使用する場合は吸入器に適応可能な液剤として、点眼
剤として使用する場合も液剤又は懸濁化剤として用い
る。特に鼻閉症治療のための点鼻薬として用いる場合、
通常の製剤化の方法に従って、液剤、懸濁化剤として用
いるか、あるいは粉末化剤(例、ヒドロキシプロピルセ
ルロース、カーボポール)等を加え、粉末剤として鼻孔
に加える。あるいは、低沸点の溶媒とともに特殊な容器
に充填し、噴射剤として用いることができる。
媒、基剤等を用いて製造することができる。例えば、錠
剤の場合、活性成分と補助成分を一緒に圧縮又は成型す
る。補助成分としては、製剤的に許容される賦形剤、例
えば結合剤(例、トウモロコシでん粉)、充填剤(例、
ラクトーク、微結晶性セルロース)、崩壊剤(例、でん
粉グリコール酸ナトリウム)又は滑沢剤(例、ステアリ
ン酸マグネシウム)などが用いられる。錠剤は、適宜、
コーティングしてもよい。シロップ剤、液剤、懸濁剤な
どの液体製剤の場合、例えば、懸濁化剤(例、メチルセ
ルロース)、乳化剤(例、レシチン)、保存剤などを用
いる。注射用製剤の場合、溶液、懸濁液又は油性もしく
は水性乳濁液の形態のいずれでもよく、これらは懸濁安
定剤又は分散剤などを含有していてもよい。吸入剤とし
て使用する場合は吸入器に適応可能な液剤として、点眼
剤として使用する場合も液剤又は懸濁化剤として用い
る。特に鼻閉症治療のための点鼻薬として用いる場合、
通常の製剤化の方法に従って、液剤、懸濁化剤として用
いるか、あるいは粉末化剤(例、ヒドロキシプロピルセ
ルロース、カーボポール)等を加え、粉末剤として鼻孔
に加える。あるいは、低沸点の溶媒とともに特殊な容器
に充填し、噴射剤として用いることができる。
化合物(I)の投与量は、投与形態、患者の症状、年
令、体重、性別、あるいは併用される薬物(あるとすれ
ば)などにより異なり、最終的には医師の判断に委ねら
れるが、経口投与の場合、体重1kgあたり、1日0.01〜1
00mg、好ましくは0.01〜10mg、より好ましくは0.1〜10m
g、非口投与の場合、体重1kgあたり、1日0.001〜100m
g、好ましくは0.001〜1mg、より好ましくは0.01〜1mgを
投与する。これを1〜4回に分割して投与すればよい。
令、体重、性別、あるいは併用される薬物(あるとすれ
ば)などにより異なり、最終的には医師の判断に委ねら
れるが、経口投与の場合、体重1kgあたり、1日0.01〜1
00mg、好ましくは0.01〜10mg、より好ましくは0.1〜10m
g、非口投与の場合、体重1kgあたり、1日0.001〜100m
g、好ましくは0.001〜1mg、より好ましくは0.01〜1mgを
投与する。これを1〜4回に分割して投与すればよい。
以下に実施例を挙げて本発明を詳しく説明するが、こ
れらは単なる例示であり本発明はこれらに限定されるも
のではない。
れらは単なる例示であり本発明はこれらに限定されるも
のではない。
実施例1 窒素気流下、(Z)−7−[(1S,2R,3R,4R)−3−
アミノビシクロ[2.2.1]ヘプト−2−イル]−5−ヘ
プテン酸メチル(II−1)(251mg,1.00mmol)を塩化メ
チレン(8ml)に溶解し、トリエチルアミン(0.238ml,
2.00mmol)を加えた後、氷冷下、2−クロロスルフォニ
ルジベンゾフラン(350mg,1.31mmol)を加え30分攪拌
し、室温まで昇温した。反応液をシリカゲルカラムクロ
マトグラフィー(n−ヘキサン−酢酸エチル1:4)で精
製し、n−ヘキサン(10ml)より結晶化して、(Z)−
7−[(1S,2R,3R,4R)−3−(2−ジベンゾフリル)
スルホニルアミノビシクロ[2.2.1]ヘプト−2−イ
ル]−5−ヘプテン酸メチル(1a−1)(342mg,0.710m
mol)を得た。収率71%。
アミノビシクロ[2.2.1]ヘプト−2−イル]−5−ヘ
プテン酸メチル(II−1)(251mg,1.00mmol)を塩化メ
チレン(8ml)に溶解し、トリエチルアミン(0.238ml,
2.00mmol)を加えた後、氷冷下、2−クロロスルフォニ
ルジベンゾフラン(350mg,1.31mmol)を加え30分攪拌
し、室温まで昇温した。反応液をシリカゲルカラムクロ
マトグラフィー(n−ヘキサン−酢酸エチル1:4)で精
製し、n−ヘキサン(10ml)より結晶化して、(Z)−
7−[(1S,2R,3R,4R)−3−(2−ジベンゾフリル)
スルホニルアミノビシクロ[2.2.1]ヘプト−2−イ
ル]−5−ヘプテン酸メチル(1a−1)(342mg,0.710m
mol)を得た。収率71%。
融点:115−116℃ 元素分析(C27H31NO5sとして) 計算値(%):C,67.34;H,6.49;N,2.91;S,6.66 実測値(%):C,67.16;H,6.47;N,2.99;S,6.66 IR(CHCl3):3382,3024,2952,2874,1726,1583,1465,1
442,1319,1245,1154,1121,1104,1071,1019,890,840,817
/cm。
442,1319,1245,1154,1121,1104,1071,1019,890,840,817
/cm。
1H NMR(CDCl3)δ:0.94−1.92(14H,m),2.15−2.24
(3H,m),2.99−3.07(1H,m),3.66(3H,s),4.98(1H,
d,J=6.6Hz),5.10−5.22(2H,m),7.39−7.46(1H,
m),7.51−7.70(3H,m),7.87−8.13(2H,m),8.53(1
H,d,J=2.1Hz)。
(3H,m),2.99−3.07(1H,m),3.66(3H,s),4.98(1H,
d,J=6.6Hz),5.10−5.22(2H,m),7.39−7.46(1H,
m),7.51−7.70(3H,m),7.87−8.13(2H,m),8.53(1
H,d,J=2.1Hz)。
[α]D=−0.6゜(CHCl3,c=1.01%,23℃). ([α]365=+37.0゜(CHCl3,c=1.01%,23℃). (Z)−7−[(1S,2R,3R,4R)−3−(2−ジベン
ゾフリル)スルホニルアミノビシクロ[2.2.1]ヘプト
−2−イル]−5−ヘプテン酸メチル(1a−1)(234m
g,0.50mmol)をメタノール(6ml)−テトラヒドロフラ
ン(4ml)に溶解し、氷冷下1N水酸化カリウム(1.50ml,
1.50mmol)を加えた後、室温まで昇温し、16時間反応さ
せた。溶媒を溜去した後、残渣に酢酸エチル(50ml)と
水(10ml)を加え、さらに1N塩酸(2.00ml,2.00mmol)
を加え、有機層を分取した。有機層を飽和食塩水で洗っ
た後、無水硫酸ナトリウムで乾燥した。溶媒を溜去した
後、残渣をシリカゲルカラムクロマトグラフィー(n−
ヘキサン−酢酸エチル=1:1,0.2%酢酸)で精製し、
(Z)−7−[(1S,2R,3R,4R)−3−(2−ジベンゾ
フリル)スルホニルアミノビシクロ[2.2.1]ヘプト−
2−イル]−5−ヘプテン酸メチル(1a−2)(203mg,
0.434mmol)を得た。収率87%。
ゾフリル)スルホニルアミノビシクロ[2.2.1]ヘプト
−2−イル]−5−ヘプテン酸メチル(1a−1)(234m
g,0.50mmol)をメタノール(6ml)−テトラヒドロフラ
ン(4ml)に溶解し、氷冷下1N水酸化カリウム(1.50ml,
1.50mmol)を加えた後、室温まで昇温し、16時間反応さ
せた。溶媒を溜去した後、残渣に酢酸エチル(50ml)と
水(10ml)を加え、さらに1N塩酸(2.00ml,2.00mmol)
を加え、有機層を分取した。有機層を飽和食塩水で洗っ
た後、無水硫酸ナトリウムで乾燥した。溶媒を溜去した
後、残渣をシリカゲルカラムクロマトグラフィー(n−
ヘキサン−酢酸エチル=1:1,0.2%酢酸)で精製し、
(Z)−7−[(1S,2R,3R,4R)−3−(2−ジベンゾ
フリル)スルホニルアミノビシクロ[2.2.1]ヘプト−
2−イル]−5−ヘプテン酸メチル(1a−2)(203mg,
0.434mmol)を得た。収率87%。
オイル IR(CHCl3):3266,3026,2952,2874,1708,1465,1443,1
423,1319,1267,1245,1153,1121,1104,1072,906/cm。
423,1319,1267,1245,1153,1121,1104,1072,906/cm。
1H NMR(CDCl3)δ:0.93−1.94(14H,m),2.12−2.19
(1H,m),2.26(2H,t,J=7.2Hz),3.00−3.08(1H,m),
5.12−5.25(2H,m),5.26(1H,d,J=6.6Hz),7.38−7.4
5(1H,m),7.51−7.70(3H,m),7.87−8.13(2H,m),8.
54(1H,d,J=2.1Hz)。
(1H,m),2.26(2H,t,J=7.2Hz),3.00−3.08(1H,m),
5.12−5.25(2H,m),5.26(1H,d,J=6.6Hz),7.38−7.4
5(1H,m),7.51−7.70(3H,m),7.87−8.13(2H,m),8.
54(1H,d,J=2.1Hz)。
[α]D=+6.8゜(CHCl3,c=1.08%,23℃)。
(Z)−7−[(1S,2R,3R,4R)−3−(2−ジベン
ゾフリル)スルホニルアミノビシクロ[2.2.1]ヘプト
−2−イル]−5−ヘプテン酸(1a−2)(453mg,0.97
mmol)をメタノール(5ml)に溶解し、氷冷下1Nナトリ
ウムメトキシド/メタノール溶液(1.034規定,0.937ml,
0.97mmol)を加えた後、室温まで昇温し、1時間反応さ
せた。溶媒を溜去して、ナトリウム塩(1a−3)(457m
g,0.933mmol)を得た。収率96%。
ゾフリル)スルホニルアミノビシクロ[2.2.1]ヘプト
−2−イル]−5−ヘプテン酸(1a−2)(453mg,0.97
mmol)をメタノール(5ml)に溶解し、氷冷下1Nナトリ
ウムメトキシド/メタノール溶液(1.034規定,0.937ml,
0.97mmol)を加えた後、室温まで昇温し、1時間反応さ
せた。溶媒を溜去して、ナトリウム塩(1a−3)(457m
g,0.933mmol)を得た。収率96%。
無晶状粉末 元素分析(C26H28NO5SNa・0.6H2Oとして) 計算値(%):C,62.41;H,5.88;N,2.80;S,6.41;Na,4.5
9 実測値(%):C,62.45;H,5.92;N,2.99;S,6.49;Na,4.4
6 IR(KBr):3434,3280,3074,3007,2952,2873,1566,146
7,1444,1417,1344,1315,1270,1248,1200,1189,1154,112
4,1107,1075,1058,895,842,818/cm。
9 実測値(%):C,62.45;H,5.92;N,2.99;S,6.49;Na,4.4
6 IR(KBr):3434,3280,3074,3007,2952,2873,1566,146
7,1444,1417,1344,1315,1270,1248,1200,1189,1154,112
4,1107,1075,1058,895,842,818/cm。
1H NMR(CD3OD)δ:1.02−2.05(16H,m),2.16−2.23
(1H,m),2.94−3.00(1H,m),4.98−5.05(2H,m),7.4
1−7.48(1H,m),7.53−7.62(1H,m),7.66(1H,d,J=
8.4Hz),7.77(1H,d,J=8.4Hz),8.57(1H,d,J=2.1H
z)。
(1H,m),2.94−3.00(1H,m),4.98−5.05(2H,m),7.4
1−7.48(1H,m),7.53−7.62(1H,m),7.66(1H,d,J=
8.4Hz),7.77(1H,d,J=8.4Hz),8.57(1H,d,J=2.1H
z)。
[α]D=−15.2゜(CH3OH,c=1.07%,22℃)。
実施例2 (Z)−7−[(1S,2R,3R,4R)−3−アミノビシク
ロ[2.2.1]ヘプト−2−イル]−5−ヘプテン酸メチ
ル トリフルオロ酢酸塩(II−2)(特公平5−79060
号、参考例4に準じて製造)232mg(0.636mmol)を塩化
メチレン(5ml)に溶解し、氷冷下、トリエチルアミン
0.279ml(2.0mmol)と4−ビフェニルカルボニルクロリ
ドを加え、同温度で7時間撹拌する。反応液をシリカゲ
ルカラムクロマトグラフィー(酢酸エチル:ヘキサン=
1:4)で精製し、(Z)−7−[(1S,2R,3R,4R)−3−
(4−ビフェニル)カルボニルアミノビシクロ[2.2.
1]ヘプト−2−イル]−5−ヘプテン酸メチル(1k−1
1)221mg(0.512mmol)を得た。この化合物(1k−11)
(190mg,0.44mmol)をメタノール(6ml)に溶解し、氷
冷下1N KOH(1.10ml,1.10mmol)を加え室温で15時間撹
拌した。反応液を減圧下濃縮した後、残渣に水(20ml)
と1N HCl(2ml)を加え、酢酸エチルで抽出した。有機
層を飽和食塩水で洗った後硫酸ナトリウムで乾燥後、濃
縮した。残渣をシリカゲルカラムクロマトグラフィー
(酢酸エチル:ヘキサン=1:1)(0.3%酢酸)で精製し
て(Z)−7−[(1S,2R,3R,4R)−3−(4−ビフェ
ニル)カルボニルアミノビシクロ[2.2.1]ヘプト−2
−イル]−5−ヘプテン酸(1k−12)172mg(0.412mmo
l)を得た。収率94%。
ロ[2.2.1]ヘプト−2−イル]−5−ヘプテン酸メチ
ル トリフルオロ酢酸塩(II−2)(特公平5−79060
号、参考例4に準じて製造)232mg(0.636mmol)を塩化
メチレン(5ml)に溶解し、氷冷下、トリエチルアミン
0.279ml(2.0mmol)と4−ビフェニルカルボニルクロリ
ドを加え、同温度で7時間撹拌する。反応液をシリカゲ
ルカラムクロマトグラフィー(酢酸エチル:ヘキサン=
1:4)で精製し、(Z)−7−[(1S,2R,3R,4R)−3−
(4−ビフェニル)カルボニルアミノビシクロ[2.2.
1]ヘプト−2−イル]−5−ヘプテン酸メチル(1k−1
1)221mg(0.512mmol)を得た。この化合物(1k−11)
(190mg,0.44mmol)をメタノール(6ml)に溶解し、氷
冷下1N KOH(1.10ml,1.10mmol)を加え室温で15時間撹
拌した。反応液を減圧下濃縮した後、残渣に水(20ml)
と1N HCl(2ml)を加え、酢酸エチルで抽出した。有機
層を飽和食塩水で洗った後硫酸ナトリウムで乾燥後、濃
縮した。残渣をシリカゲルカラムクロマトグラフィー
(酢酸エチル:ヘキサン=1:1)(0.3%酢酸)で精製し
て(Z)−7−[(1S,2R,3R,4R)−3−(4−ビフェ
ニル)カルボニルアミノビシクロ[2.2.1]ヘプト−2
−イル]−5−ヘプテン酸(1k−12)172mg(0.412mmo
l)を得た。収率94%。
下記に示す化合物は、以下の方法でも製造できる。
実施例3 窒素雰囲気下、4−カルボキシブチルトリフェニルホ
スホニウムブロマイド(14.8mg、33.3mmol)およびテト
ラヒドロフラン(80ml)から成る懸濁液にカリウムt−
ブチレート(7.55g、67.3mmol)を室温で加える。室温
のまま1時間撹拌した後、−20℃に冷却してN−[(1
S,2S,3S,4R)−3−ホルミルメチルビシクロ[2.2.1]
ヘプト−2−イル]ベンゼンスルホンアミド(III−
1)(特開平2−256650号、参考例2)(3.25g、11.1m
mol)のテトラヒドロフラン溶液(20ml)をゆっくり加
える。−20℃で約1時間半撹拌を続けた後、氷浴を除
き、更に1時間撹拌する。反応液に2N塩酸を加え酢酸エ
チルで抽出し、水及び食塩水で洗浄後濃縮する。得られ
た粗生成物にトルエンと1N水酸化ナトリウム溶液を加え
て水層を分取する。有機層をもう一度水洗し、先程の水
層と合わせた後、2N塩酸を加える。酢酸エチルで抽出
後、水及び食塩水で洗浄し、硫酸ナトリウムで乾燥後濃
縮する。残渣をシリカゲルカラムクロマトグラフィーに
より精製し、(Z)−7−[(1R,2S,3S,4S)−3−フ
ェニルスルホニルアミノビシクロ[2.2.1]ヘプト−2
−イル]−5−ヘプテン酸カルシウム(1d−1)を得る
(3.29g、収率79%)。
スホニウムブロマイド(14.8mg、33.3mmol)およびテト
ラヒドロフラン(80ml)から成る懸濁液にカリウムt−
ブチレート(7.55g、67.3mmol)を室温で加える。室温
のまま1時間撹拌した後、−20℃に冷却してN−[(1
S,2S,3S,4R)−3−ホルミルメチルビシクロ[2.2.1]
ヘプト−2−イル]ベンゼンスルホンアミド(III−
1)(特開平2−256650号、参考例2)(3.25g、11.1m
mol)のテトラヒドロフラン溶液(20ml)をゆっくり加
える。−20℃で約1時間半撹拌を続けた後、氷浴を除
き、更に1時間撹拌する。反応液に2N塩酸を加え酢酸エ
チルで抽出し、水及び食塩水で洗浄後濃縮する。得られ
た粗生成物にトルエンと1N水酸化ナトリウム溶液を加え
て水層を分取する。有機層をもう一度水洗し、先程の水
層と合わせた後、2N塩酸を加える。酢酸エチルで抽出
後、水及び食塩水で洗浄し、硫酸ナトリウムで乾燥後濃
縮する。残渣をシリカゲルカラムクロマトグラフィーに
より精製し、(Z)−7−[(1R,2S,3S,4S)−3−フ
ェニルスルホニルアミノビシクロ[2.2.1]ヘプト−2
−イル]−5−ヘプテン酸カルシウム(1d−1)を得る
(3.29g、収率79%)。
融点:62℃ 元素分析(C20H27NO4Sとして 計算値(%):C,63.63;H,7.21;N,3.71;S,8.49 実測値(%):C,63.56;H,7.21;N,3.83;S,8.43 [α]D=+5.3±0.5゜(CHCl3,C=1.003%,22℃) [α]D=+27.1±0.7゜(MeOH,C=1.015%,24℃) IR(Nujol)3282,3260,3300,2400,1708,1268,1248,12
02,1162,1153,1095,1076/cm 1H NMR δ 0.88−2.10(m,14H),2.14(br s,1H),2.
34(t,J=7.2Hz,2H),2.95−3.07(m,1H),5.13−5.35
(m,3H),7.45−7.64(m,3H),7.85−7.94(m,2H),9.5
2(br s,1H) 上記実施例と同様にして製造した化合物を以下に示
す。
02,1162,1153,1095,1076/cm 1H NMR δ 0.88−2.10(m,14H),2.14(br s,1H),2.
34(t,J=7.2Hz,2H),2.95−3.07(m,1H),5.13−5.35
(m,3H),7.45−7.64(m,3H),7.85−7.94(m,2H),9.5
2(br s,1H) 上記実施例と同様にして製造した化合物を以下に示
す。
上記化合物の物性値を以下に示す。尚、上記化合物N
o.は、表中の化合物のNo.と対応する。
o.は、表中の化合物のNo.と対応する。
No.1a−4 [α]D=−11.5゜(CHCl3,c=1.01,23.5℃). No.1a−5 [α]D=−10.0゜(CHCl3,c=1.01,25.0℃). No.1a−6 CDCl3 300MHz 0.93−1.96(14H,m),2.20−2.26(3H,m),3.03(1H,
m),3.67(3H,s),4.99(1H,d,J=6.6Hz),5.10−5.24
(2H,m),7.37−7.51(3H,m),7.54−7.64(3H,m),7.7
6−7.88(2H,m),8.11(1H,m). IR(CHCl3):3384,3278,3026,2952,2874,1727,1436,141
1,1324,1155,1097/cm. [α]D=−9.0゜(CHCl3,c=1.04,22.0℃). No.1a−7 CDCl3 300MHz 0.93−2.00(14H,m),2.18(1H,m),2.28(2H,t,J=7.2
Hz),3.04(1H,m),5.15−5.25(2H,m),5.28(1H,d,J
=6.9Hz),7.36−7.50(3H,m),7.54−7.63(3H,m),7.
76−7.89(2H,m),8.12(1H,m). IR(CHCl3):3268,3028,2952,2872,1708,1452,1410,132
4,1155,1097/cm. [α]D=−9.1゜(CHCl3,c=1.01,24.0℃). No.1a−8 CDCl3 300MHz 0.94−1.99(14H,m),2.21−2.29(3H,m),3.05(1H,
m),3.67(3H,s),4.92(1H,d,J=6.3Hz),5.14−5.30
(2H,m),7.70−7.78(6H,m),7.96−8.01(2H,m). IR(CHCl3):3376,3272,3018,2946,2868,1727,1616,143
5,1388,1324,1162,1130,1069/cm. [α]D=+1.6゜(CHCl3,c=1.01,24.0℃).mp.117−
119℃. No.1a−9 CDCl3 300MHz 0.95−2.08(14H,m),2.19(1H,m),2.32(2H,t,J=7.2
Hz),3.06(1H,m),5.20−5.30(2H,m),5.34(1H,d,J
=6.6Hz),7.69−7.78(6H,m),7.96−8.03(2H,m). IR(CHCl3):3260,3020,2950,2868,1708,1389,1324,116
2,1130,1069/cm. [α]D=+13.3゜(CHCl3,c=1.05,24.0℃). mp.118−120℃ No.1a−10 CDCl3 300MHz 0.96−1.98(14H,m),2.15−2.32(3H,m),3.04(1H,
m),3.66(3H,s),5.12−5.26(5H,m),7.67−7.78(4
H,m),7.93−8.07(4H,m). IR(CHCl3):3276,3018,2946,2868,1726,1595,1435,134
1,1162,1095/cm. [α]D=−1.5゜(CHCl3,c=1.01,25.0℃). mp.133−139℃. No.1a−11 CD3OD 300MHz 1.05−1.98(14H,m),2.13−2.22(3H,m),2.97(1H,
m),5.09−5.22(2H,m),7.85−7.92(4H,m),7.95−8.
05(4H,m). IR(KBr):3385,3261,3069,3003,2954,2872,1708,1596,
1428,1413,1378,1343,1326,1236,1186,1160,1096/cm. mp.144−146℃. No.1a−12 CDCl3 300MHz 0.96−1.96(14H,m),2.22−2.27(3H,m),3.03(1H,
m),3.66(3H,s),3.87(3H,s),4.86(1H,d,J=6.9H
z),5.18−5.24(2H,m),6.99−7.02(2H,m),7.55−7.
66(2H,m),7.66−7.69(2H,m),7.89−7.92(2H,m). IR(CHCl3):3374,3270,3016,2948,2870,1726,1608,151
8,1487,1458,1437,1248,157,1037. [α]D=+4.2゜(CHCl3,c=1.01,24.0℃). mp.85−87℃. No.1a−13 CDCl3 300MHz 0.97−1.99(14H,m),2.18(1H,m),2.30(2H,t,J=7.2
Hz),3.04(1H,m),3.86(3H,s),5.18(1H,d,J=5.7H
z),5.23−5.26(2H,m),6.99−7.02(2H,m),7.55−7.
58(2H,m),7.66−7.68(2H,m),7.89−7.92(2H,m). IR(CHCl3):3380,3260,3020,2948,2868,1708,1608,151
9,1487,1458,1306,1293,1248,1156/cm. [α]D=+18.3゜(CHCl3,c=1.00,25.5℃). No.1a−14 CDCl3 300MHz 0.98−2.00(14H,m),2.20(1H,m),2.25(2H,t,J=7.2
Hz),3.02(1H,m),3.67(3H,s),4.85(1H,d,J=6.3H
z),5.19−5.25(2H,m),7.13(1H,dd,J=4.8,3.6Hz),
7.39(1H,d,J=4.8Hz),7.40(1H,d,J=3.6Hz),7.71−
7.74(2H,m),7.86−7.89(2H,m). IR(CHCl3):3374,3270,3018,2946,2868,1727,1593,143
4,1322/cm. [α]D=+5.6゜(CHCl3,c=1.01,24℃). mp.69−71℃. No.1a−15 CDCl3 300MHz 0.95−2.00(14H,m),2.17(1H,m),2.32(2H,t,J=7.2
Hz),3.03(1H,m),5.20(1H,d,J=6.9Hz),5.24−5.28
(2H,m),7.13(1H,dd,J=4.8,3.3Hz),7.38(1H,d,J=
4.8Hz),7.43(1H,d,J=3.3Hz),7.73(2H,d,J=8.4H
z),7.87(2H,d,J=8.4Hz). IR(CHCl3):3260,3022,2948,2868,1709,1593,1404,132
1,1154/cm. [α]D=+20.8゜(CHCl3,c=1.07,23℃). mp.71−73℃. No.1a−16 CDCl3 300MHz 0.98−2.00(14H,m),2.27(2H,t,J=7.5Hz),2.28(1
H,m),3.13(1H,m),3.66(3H,s),4.90(1H,d,J=6.9H
z),5.25−5.29(2H,m),7.40−7.65(6H,m),7.76(1
H,d,J=8.4Hz),7.90−8.02(4H,m). IR(CHCl3):3376,3276,3018,2946,2868,1726,1593,143
5,1394,1322,1159/cm. [α]D=+7.0゜(CHCl3,c=1.07,24℃). No.1a−17 CDCl3 300MHz 1.02−2.07(14H,m),2.25(1H,m),2.34(2H,t,J=6.6
Hz),3.14(1H,m),5.28−5.33(3H,m),7.39−7.57(4
H,m),7.62−7.65(2H,m),7.76(1H,d,J=8.1Hz),7.8
9−8.02(4H,m). IR(CHCl3):3260,2948,2868,1709,1593,1394,1324,115
7/cm. [α]D=+20.2゜(CHCl3,c=1.02,24℃). No.1a−18 CDCl3 300MHz 1.05−1.97(14H,m),2.25(2H,t,J=7.2Hz),2.33(1
H,m),3.12(1H,m),3.67(3H,s),4.91(1H,d,J=6.6H
z),5.24−5.29(2H,m),7.24(1H,d,J=3.9Hz),7.39
−7.45(3H,m),7.56(1H,d,J=3.9Hz),7.59−7.62(2
H,m). IR(CHCl3):3372,3272,3018,2946,2868,1727,1433,133
1,1152/cm. [α]D=−5.7゜(CHCl3,c=1.01,23℃). No.1a−19 CDCl3 300MHz 1.05−2.05(14H,m),2.28−2.33(3H,m),3.13(1H,
m),5.18(1H,d,J=6.3Hz),5.27−5.31(2H,m),7.24
(1H,d,J=4.2Hz),7.39−7.42(3H,m),7.56(1H,d,J
=4.2Hz),7.58−7.62(2H,m). IR(CHCl3):3372,3254,3018,2948,2868,1707,1431,132
8,1151/cm. [α]D=+4.5゜(CHCl3,c=1.01,21.5℃). No.1a−20 CDCl3 300MHz 1.05−2.00(14H,m),2.26(2H,t,J=7.5Hz),2.33(1
H,m),3.11(1H,m),3.68(3H,s),4.92(1H,d,J=6.0H
z),5.27(2H,m),7.05(1H,m),7.10(1H,d,J=3.6H
z),7.25(1H,m),7.32(1H,m),7.49(1H,d,J=3.6H
z). IR(CHCl3):3372,3272,3018,2946,2686,1727,1438,141
7,1333,1151/cm. [α]D=−9.2゜(CHCl3,c=1.01,25℃). No.1a−21 CDCl3 300MHz 1.02−2.01(14H,m),2.28−2.34(3H,m),3.13(1H,
m),5.12(1H,d,J=6.9Hz),5.28−5.32(2H,m),7.06
(1H,m),7.10(1H,d,J=3.9Hz),7.25(1H,m),7.32
(1H,m),7.50(1H,d,J=3.9Hz). IR(CHCl3):3350,3250,2948,1709,1440,1420,1330,115
1. [α]D=+2.5゜(CHCl3,c=1.00,25℃). No.1a−22 CDCl3 300MHz 0.96−2.05(14H,m),2.25(1H,m),2.35(2H,t,J=7.0
Hz),3.11(1H,m),5.20−5.34(2H,m),5. 41(1H,d,J=6.6Hz),7.31−7.49(5H,m),7.62(1H,d,
J=7.8Hz),8.11(1H,d.d,J=1.8and7.8Hz),8.35(1H,
d,J=1.8Hz). IR(CHCl3):3384,3271,3025,2958,1708,1608,1559,153
7,1357,1168/cm. [α]D=+18.3(CHCl3,C=0.31,22℃). No.1a−23 CDCl3 300MHz 0.97−2.07(14H,m),2.24(1H,m),2.35(2H,t,J=6.9
Hz),3.09(1H,m),3.86(3H,s),5.24−5.35(2H,m),
5.44(1H,d,J=6.3Hz),6.97−7.00(2H,m),7.26−7.2
8(2H,m),7.59(1H,d,J=8.1Hz),8.06(1H,d.d,J=2.
1and8.1Hz),8.29(1H,d,J=2.1Hz). IR(CHCl3):3384,3270,2959,1709,1609,1535,1519,135
7,1302,1255,1226,1169/cm. [α]D=+17.0゜(CHCl3,C=1.00,21℃). No.1No.1a−24 CDCl3 300MHz 0.95−2.00(14H,m),2.20−2.25(1H,m),2.26(2H,t,
J=7.2Hz),3.02−3.10(1H,m),3.66(3H,s),4.92(1
H,d,J=6.6Hz),5.16−5.31(2H,m),7.52−7.60(3H,
m),7.94−8.06(6H,m). IR(CHCl3):3376,3020,2946,2868,1726,1436,1366,129
8,1164,1090,890/cm. [α]D=+11.2±0.5゜(CHCl3,c=1.04,23.5℃) mp.101−103℃ No.1a−25 CDCl3 300MHz 0.95−2.08(14H,m),2.15−2.22(1H,m),2.33(2H,t,
J=6.9Hz),3.02−3.10(1H,m),5.21−5.31(2H,m),
5.34(1H,d,J=6.3Hz),7.51−7.59(3H,m),7.92−8.0
7(6H,m). IR(CHCl3):3258,3022,2948,2868,1707,1399,1328,129
8,1163,1089,1051,892/cm [α]D==+29.8±0.7゜(CHCl3,c=1.05,25℃) mp.158−160℃ No.1a−26 Anal.Calcd for C26H30N3O4SNa 0.8H2O:C,60.29;H,6.1
5;N,8.11;S,6.19;Na,4.44. Found:C,60.15;H,6.19;N,8.15;S,6.03;Na,4.98. [α]D=−16.6゜(CHCl3,c=1.04,25.0℃). No.1a−27 CDCl3 300MHz 0.92−1.98(14H,m),2.20(1H,m),2.26(2H,t,J=7.5
Hz),3.03(1H,m),3.12(6H,s),3.66(3H,s),4.87
(1H,d,J=6.6Hz),5.16−5.32(2H,m),6.73−6.80(2
H,m),7.88−8.00(6H,m). IR(CHCl3):3376,3020,2946,1726,1601,1518,1442,141
9,1362,1312,1163,1133,1088/cm. [α]D==+55.3゜(CHCl3,c=0.53,24.0℃). mp.158−168℃ No.1a−28 CDCl3+CD3OD 300MHz 0.99−2.14(14H,m),2.21(1H,m),2.31(2H,t,J=7.2
Hz),2.94(1H,m),3.12(6H,s),5.22−5.38(2H,m),
6.73−6.81(2H,m),7.87−8.00(6H,m). IR(KBr):3434,3309,2946,1708,1604,1520,1442,1416,
1366,1312,1252,1164,1155,1134,1091/cm. [α]D=測定不能(着色,エネルギー不足) mp.193−196℃ No.1a−29 CD3OD 300MHz 1.02−1.96(14H,m),2.10(2H,t,J=7.8Hz),2.16(1
H,m),2.98(1H,m),3.11(6H,s),5.07−5.27(2H,
m),6.80−6.87(2H,m),7.84−8.00(6H,m). IR(KBr):3433,3087,3004,2949,2871,1604,1565,1520,
1444,1420,1364,1312,1253,11638,1136,1090/cm. [α]D=測定不能 No.1a−30 CDCl3 300MHz 0.95−1.99(14H,m),2.22(1H,m),2.26(2H,t,J=7.2
Hz),2.35(3H,s),3.06(1H,m),3.66(3H,s),4.95
(1H,d,J=6.9Hz),5.15−5.30(2H,m),7.26−7.32(2
H,m),7.97−8.06(6H,m). IR(CHCl3):3374,2996,2946,2868,1763,1728,1591,149
5,1435,1368,1299,1228,1192,1163,1139/cm. [α]D==+12.9゜(CHCl3,c=1.04,26.0℃). No.1a−31 CDCl3 300MHz 0.93−2.01(14H,m),2.19(1H,m),2.31(2H,t,J=7.2
Hz),2.35(3H,s),3.06(1H,m),5.17−5.32(2H,m),
7.25−7.32(2H,m),7.96−8.07(6H,m). IR(CHCl3):3267,3028,2952,2874,1759,1708,1592,149
5,1368,1328,1299,1163,1138,1088,1050,1008/cm. [α]D=+21.7゜(CHCl3,C=0.51,22℃). No.1a−32 CDCl3 300MHz 0.93−1.99(14H,m),2.21(1H,m),2.27(2H,t,J=7.2
Hz),3.05(1H,m),3.67(3H,s),4.92(1H,d,J=6.6H
z),5.15−5.30(2H,m),6.72(1H,s),6.96−7.00(2
H,m),7.86−8.04(6H,m). IR(CHCl3):3374,3276,3018,2946,2686,1725,1605,158
9,1502,1433,1396,1330,1271,1164,1135,1089/cm.
[α]D=+18.6゜(CHCl3,c=1.00,26.0℃). No.1a−33 CDCl3+CD3OD 300MHz 0.98−2.08(14H,m),2.20(1H,m),2.28(2H,t,J=7.2
Hz),2.98(1H,m),5.18−5.32(2H,m),6.92−6.99(2
H,m),7.85−8.02(6H,m). IR(KBr):3385,3248,2948,2876,1717,1601,1505,1430,
1399,1296,1280,1219,1165,1136,1092/cm. [α]D=−16.0゜(CH3OH,c=1.08,26.0℃). mp.208−210℃ No.1a−34 mp.82−83℃ [α]D=+10.6゜(CHCl3,c=1.01,23.
5℃). No.1a−35 mp.80−82℃ [α]D=−1.8゜(CHCl3,c=1.07,22.0
℃). No.1a−36 TLC Rf=0.25(酢酸エチル−n−ヘキサン=1:1(0.3
%酢酸)) No.1a−37 CDCl3 300MHz 0.92−1.96(14H,m),2.21(1H,m),2.27(2H,t,J=7.2
Hz),3.01(1H,m),3.66(3H,s),4.71(1H,d,J=6.6H
z),5.14−5.29(2H,m),7.12(1H,d,J=16.2Hz),7.24
(1H,d,J=16.2Hz),7.28−7.42(3H,m),7.52−7.56
(2H,m),7.62(2H,d,J=8.7Hz),7.85(2H,d,J=8.7H
z). IR(CHCl3):3384,3283,3023,2954,2876,1730,1595,149
4,1317,1163,1147/cm. [α]D=+10.5゜(CHCl3,c=1.01,24℃). mp.116−117℃. No.1a−38 CDCl3 300MHz 0.92−1.99(14H,m),2.17(1H,m),2.32(2H,t,J=7.2
Hz),3.02(1H,m),5.23−5.29(3H,m),7.11(1H,d,J
=16.2Hz),7.23(1H,d,J=16.2Hz),7.28−7.41(3H,
m),7.52−7.55(2H,m),7.61(2H,d,J=8.7Hz),7.86
(2H,d,J=8.7Hz). IR(CHCl3):3515,3384,3270,3022,3015,2957,2876,266
9,1708,1595,1496,1320,1157/cm. [α]D=+27.1゜(CHCl3,c=1.02,24℃). No.1a−39 CDCl3 300MHz 0.92−1.99(14H,m),2.15(1H,m),2.28(2H,t,J=7.4
Hz),3.01(1H,m),3.68(3H,s),4.96(1H,d,J=6.6H
z),5.16−5.32(2H,m),6.60(1H,d,J=12.0Hz),6.74
(1H,d,J=12.0Hz),7.16−7.23(5H,m),7.35(2H,d,J
=8.4Hz),7.72(2H,d,J=8.4Hz). IR(CHCl3):3384,3283,3023,3015,2954,2876,1730,159
5,1493,1324,1163,1147/cm. [α]D=+13.7゜(CHCl3,c=1.00,24℃). No.1a−40 CDCl3 300MHz 0.90−2.16(14H,m),2.12(1H,m),2.34(2H,t,J=7.2
Hz),3.02(1H,m),5.16(1H,d,J=6.9Hz),5.23−5.34
(2H,m),6.60(1H,d,J=12.3Hz),6.74(1H,d,J=12.3
Hz),7.14−7.24(5H,m),7.35(2H,d,J=8.1Hz),7.72
(2H,d,J=8.1Hz). IR(CHCl3):3515,3384,3269,3025,3021,3014,2957,287
6,2668,1709,1595,1322,1162,1147/cm. [α]D=+26.4゜(CHCl3,c=1.00,24℃). No.1a−41 CDCl3 300MHz 0.98−1.99(14H,m),2.17(1H,m),2.32(2H,t,J=7.2
Hz),3.00(1H,m),3.84(3H,s),5.20−5.26(3H,m),
6.90−6.95(2H,m),6.98(1H,d,J=16.2Hz),7.17(1
H,d,J=16.2Hz),7.46−7.49(2H,m),7.58(2H,d,J=
8.4Hz),7.83(2H,d,J=8.4Hz). IR(CHCl3):3258,3018,3002,2950,1709,1590,1509,145
7,1404,1302,1250,1153/cm. [α]D=+30.2゜(CHCl3,c=1.00,23℃). mp.99−100℃ No.1a−42 CDCl3 300MHz 1.01−1.99(14H,m),2.28(2H,t,J=7.2Hz),2.30(1
H,m),3.10(1H,m),3.66(3H,s),5.07(1H,br),5.25
−5.30(2H,m),6.98−7.04(2H,m),7.16(1H,d,J=1
6.2Hz),7.28−7.37(3H,m),7.47−7.50(3H,m). IR(CHCl3):3372,3276,3020,2946,2870,1727,1491,143
3,1331,1152/cm. [α]D=−11.5゜(CHCl3,c=1.07,21.5℃). No.1a−43 CDCl3 300MHz 0.98−2.00(14H,m),2.11−2.36(3H,m),3.12(1H,
m),5.10(1H,d,J=6.6Hz),5.29−5.32(2H,m),6.99
−7.04(2H,m),7.23(1H,d,J=21.6Hz),7.32−7.49
(6H,m). IR(CHCl3):3380,3248,3020,2948,2868,1709,1491,143
0,1329,1151/cm. [α]D=+3.4゜(CHCl3,c=1.03,25℃). No.1a−44 CDCl3 300MHz 1.00−2.00(14H,m),2.13(1H,m),2.29(2H,t,J=7.4
Hz),2.90−3.13(5H,m),3.68(3H,s),4.74(1H,d,J
=6.6Hz),5.15−5.30(2H,m),7.18−7.29(7H,m),7.
76(2H,d,J=8.1Hz). IR(CHCl3):3384,3282,3063,3028,3023,3016,2953,287
6,1730,1599,1496,1319,1157/cm. [α]D=+2.3゜(CHCl3,c=1.00,25℃)。
m),3.67(3H,s),4.99(1H,d,J=6.6Hz),5.10−5.24
(2H,m),7.37−7.51(3H,m),7.54−7.64(3H,m),7.7
6−7.88(2H,m),8.11(1H,m). IR(CHCl3):3384,3278,3026,2952,2874,1727,1436,141
1,1324,1155,1097/cm. [α]D=−9.0゜(CHCl3,c=1.04,22.0℃). No.1a−7 CDCl3 300MHz 0.93−2.00(14H,m),2.18(1H,m),2.28(2H,t,J=7.2
Hz),3.04(1H,m),5.15−5.25(2H,m),5.28(1H,d,J
=6.9Hz),7.36−7.50(3H,m),7.54−7.63(3H,m),7.
76−7.89(2H,m),8.12(1H,m). IR(CHCl3):3268,3028,2952,2872,1708,1452,1410,132
4,1155,1097/cm. [α]D=−9.1゜(CHCl3,c=1.01,24.0℃). No.1a−8 CDCl3 300MHz 0.94−1.99(14H,m),2.21−2.29(3H,m),3.05(1H,
m),3.67(3H,s),4.92(1H,d,J=6.3Hz),5.14−5.30
(2H,m),7.70−7.78(6H,m),7.96−8.01(2H,m). IR(CHCl3):3376,3272,3018,2946,2868,1727,1616,143
5,1388,1324,1162,1130,1069/cm. [α]D=+1.6゜(CHCl3,c=1.01,24.0℃).mp.117−
119℃. No.1a−9 CDCl3 300MHz 0.95−2.08(14H,m),2.19(1H,m),2.32(2H,t,J=7.2
Hz),3.06(1H,m),5.20−5.30(2H,m),5.34(1H,d,J
=6.6Hz),7.69−7.78(6H,m),7.96−8.03(2H,m). IR(CHCl3):3260,3020,2950,2868,1708,1389,1324,116
2,1130,1069/cm. [α]D=+13.3゜(CHCl3,c=1.05,24.0℃). mp.118−120℃ No.1a−10 CDCl3 300MHz 0.96−1.98(14H,m),2.15−2.32(3H,m),3.04(1H,
m),3.66(3H,s),5.12−5.26(5H,m),7.67−7.78(4
H,m),7.93−8.07(4H,m). IR(CHCl3):3276,3018,2946,2868,1726,1595,1435,134
1,1162,1095/cm. [α]D=−1.5゜(CHCl3,c=1.01,25.0℃). mp.133−139℃. No.1a−11 CD3OD 300MHz 1.05−1.98(14H,m),2.13−2.22(3H,m),2.97(1H,
m),5.09−5.22(2H,m),7.85−7.92(4H,m),7.95−8.
05(4H,m). IR(KBr):3385,3261,3069,3003,2954,2872,1708,1596,
1428,1413,1378,1343,1326,1236,1186,1160,1096/cm. mp.144−146℃. No.1a−12 CDCl3 300MHz 0.96−1.96(14H,m),2.22−2.27(3H,m),3.03(1H,
m),3.66(3H,s),3.87(3H,s),4.86(1H,d,J=6.9H
z),5.18−5.24(2H,m),6.99−7.02(2H,m),7.55−7.
66(2H,m),7.66−7.69(2H,m),7.89−7.92(2H,m). IR(CHCl3):3374,3270,3016,2948,2870,1726,1608,151
8,1487,1458,1437,1248,157,1037. [α]D=+4.2゜(CHCl3,c=1.01,24.0℃). mp.85−87℃. No.1a−13 CDCl3 300MHz 0.97−1.99(14H,m),2.18(1H,m),2.30(2H,t,J=7.2
Hz),3.04(1H,m),3.86(3H,s),5.18(1H,d,J=5.7H
z),5.23−5.26(2H,m),6.99−7.02(2H,m),7.55−7.
58(2H,m),7.66−7.68(2H,m),7.89−7.92(2H,m). IR(CHCl3):3380,3260,3020,2948,2868,1708,1608,151
9,1487,1458,1306,1293,1248,1156/cm. [α]D=+18.3゜(CHCl3,c=1.00,25.5℃). No.1a−14 CDCl3 300MHz 0.98−2.00(14H,m),2.20(1H,m),2.25(2H,t,J=7.2
Hz),3.02(1H,m),3.67(3H,s),4.85(1H,d,J=6.3H
z),5.19−5.25(2H,m),7.13(1H,dd,J=4.8,3.6Hz),
7.39(1H,d,J=4.8Hz),7.40(1H,d,J=3.6Hz),7.71−
7.74(2H,m),7.86−7.89(2H,m). IR(CHCl3):3374,3270,3018,2946,2868,1727,1593,143
4,1322/cm. [α]D=+5.6゜(CHCl3,c=1.01,24℃). mp.69−71℃. No.1a−15 CDCl3 300MHz 0.95−2.00(14H,m),2.17(1H,m),2.32(2H,t,J=7.2
Hz),3.03(1H,m),5.20(1H,d,J=6.9Hz),5.24−5.28
(2H,m),7.13(1H,dd,J=4.8,3.3Hz),7.38(1H,d,J=
4.8Hz),7.43(1H,d,J=3.3Hz),7.73(2H,d,J=8.4H
z),7.87(2H,d,J=8.4Hz). IR(CHCl3):3260,3022,2948,2868,1709,1593,1404,132
1,1154/cm. [α]D=+20.8゜(CHCl3,c=1.07,23℃). mp.71−73℃. No.1a−16 CDCl3 300MHz 0.98−2.00(14H,m),2.27(2H,t,J=7.5Hz),2.28(1
H,m),3.13(1H,m),3.66(3H,s),4.90(1H,d,J=6.9H
z),5.25−5.29(2H,m),7.40−7.65(6H,m),7.76(1
H,d,J=8.4Hz),7.90−8.02(4H,m). IR(CHCl3):3376,3276,3018,2946,2868,1726,1593,143
5,1394,1322,1159/cm. [α]D=+7.0゜(CHCl3,c=1.07,24℃). No.1a−17 CDCl3 300MHz 1.02−2.07(14H,m),2.25(1H,m),2.34(2H,t,J=6.6
Hz),3.14(1H,m),5.28−5.33(3H,m),7.39−7.57(4
H,m),7.62−7.65(2H,m),7.76(1H,d,J=8.1Hz),7.8
9−8.02(4H,m). IR(CHCl3):3260,2948,2868,1709,1593,1394,1324,115
7/cm. [α]D=+20.2゜(CHCl3,c=1.02,24℃). No.1a−18 CDCl3 300MHz 1.05−1.97(14H,m),2.25(2H,t,J=7.2Hz),2.33(1
H,m),3.12(1H,m),3.67(3H,s),4.91(1H,d,J=6.6H
z),5.24−5.29(2H,m),7.24(1H,d,J=3.9Hz),7.39
−7.45(3H,m),7.56(1H,d,J=3.9Hz),7.59−7.62(2
H,m). IR(CHCl3):3372,3272,3018,2946,2868,1727,1433,133
1,1152/cm. [α]D=−5.7゜(CHCl3,c=1.01,23℃). No.1a−19 CDCl3 300MHz 1.05−2.05(14H,m),2.28−2.33(3H,m),3.13(1H,
m),5.18(1H,d,J=6.3Hz),5.27−5.31(2H,m),7.24
(1H,d,J=4.2Hz),7.39−7.42(3H,m),7.56(1H,d,J
=4.2Hz),7.58−7.62(2H,m). IR(CHCl3):3372,3254,3018,2948,2868,1707,1431,132
8,1151/cm. [α]D=+4.5゜(CHCl3,c=1.01,21.5℃). No.1a−20 CDCl3 300MHz 1.05−2.00(14H,m),2.26(2H,t,J=7.5Hz),2.33(1
H,m),3.11(1H,m),3.68(3H,s),4.92(1H,d,J=6.0H
z),5.27(2H,m),7.05(1H,m),7.10(1H,d,J=3.6H
z),7.25(1H,m),7.32(1H,m),7.49(1H,d,J=3.6H
z). IR(CHCl3):3372,3272,3018,2946,2686,1727,1438,141
7,1333,1151/cm. [α]D=−9.2゜(CHCl3,c=1.01,25℃). No.1a−21 CDCl3 300MHz 1.02−2.01(14H,m),2.28−2.34(3H,m),3.13(1H,
m),5.12(1H,d,J=6.9Hz),5.28−5.32(2H,m),7.06
(1H,m),7.10(1H,d,J=3.9Hz),7.25(1H,m),7.32
(1H,m),7.50(1H,d,J=3.9Hz). IR(CHCl3):3350,3250,2948,1709,1440,1420,1330,115
1. [α]D=+2.5゜(CHCl3,c=1.00,25℃). No.1a−22 CDCl3 300MHz 0.96−2.05(14H,m),2.25(1H,m),2.35(2H,t,J=7.0
Hz),3.11(1H,m),5.20−5.34(2H,m),5. 41(1H,d,J=6.6Hz),7.31−7.49(5H,m),7.62(1H,d,
J=7.8Hz),8.11(1H,d.d,J=1.8and7.8Hz),8.35(1H,
d,J=1.8Hz). IR(CHCl3):3384,3271,3025,2958,1708,1608,1559,153
7,1357,1168/cm. [α]D=+18.3(CHCl3,C=0.31,22℃). No.1a−23 CDCl3 300MHz 0.97−2.07(14H,m),2.24(1H,m),2.35(2H,t,J=6.9
Hz),3.09(1H,m),3.86(3H,s),5.24−5.35(2H,m),
5.44(1H,d,J=6.3Hz),6.97−7.00(2H,m),7.26−7.2
8(2H,m),7.59(1H,d,J=8.1Hz),8.06(1H,d.d,J=2.
1and8.1Hz),8.29(1H,d,J=2.1Hz). IR(CHCl3):3384,3270,2959,1709,1609,1535,1519,135
7,1302,1255,1226,1169/cm. [α]D=+17.0゜(CHCl3,C=1.00,21℃). No.1No.1a−24 CDCl3 300MHz 0.95−2.00(14H,m),2.20−2.25(1H,m),2.26(2H,t,
J=7.2Hz),3.02−3.10(1H,m),3.66(3H,s),4.92(1
H,d,J=6.6Hz),5.16−5.31(2H,m),7.52−7.60(3H,
m),7.94−8.06(6H,m). IR(CHCl3):3376,3020,2946,2868,1726,1436,1366,129
8,1164,1090,890/cm. [α]D=+11.2±0.5゜(CHCl3,c=1.04,23.5℃) mp.101−103℃ No.1a−25 CDCl3 300MHz 0.95−2.08(14H,m),2.15−2.22(1H,m),2.33(2H,t,
J=6.9Hz),3.02−3.10(1H,m),5.21−5.31(2H,m),
5.34(1H,d,J=6.3Hz),7.51−7.59(3H,m),7.92−8.0
7(6H,m). IR(CHCl3):3258,3022,2948,2868,1707,1399,1328,129
8,1163,1089,1051,892/cm [α]D==+29.8±0.7゜(CHCl3,c=1.05,25℃) mp.158−160℃ No.1a−26 Anal.Calcd for C26H30N3O4SNa 0.8H2O:C,60.29;H,6.1
5;N,8.11;S,6.19;Na,4.44. Found:C,60.15;H,6.19;N,8.15;S,6.03;Na,4.98. [α]D=−16.6゜(CHCl3,c=1.04,25.0℃). No.1a−27 CDCl3 300MHz 0.92−1.98(14H,m),2.20(1H,m),2.26(2H,t,J=7.5
Hz),3.03(1H,m),3.12(6H,s),3.66(3H,s),4.87
(1H,d,J=6.6Hz),5.16−5.32(2H,m),6.73−6.80(2
H,m),7.88−8.00(6H,m). IR(CHCl3):3376,3020,2946,1726,1601,1518,1442,141
9,1362,1312,1163,1133,1088/cm. [α]D==+55.3゜(CHCl3,c=0.53,24.0℃). mp.158−168℃ No.1a−28 CDCl3+CD3OD 300MHz 0.99−2.14(14H,m),2.21(1H,m),2.31(2H,t,J=7.2
Hz),2.94(1H,m),3.12(6H,s),5.22−5.38(2H,m),
6.73−6.81(2H,m),7.87−8.00(6H,m). IR(KBr):3434,3309,2946,1708,1604,1520,1442,1416,
1366,1312,1252,1164,1155,1134,1091/cm. [α]D=測定不能(着色,エネルギー不足) mp.193−196℃ No.1a−29 CD3OD 300MHz 1.02−1.96(14H,m),2.10(2H,t,J=7.8Hz),2.16(1
H,m),2.98(1H,m),3.11(6H,s),5.07−5.27(2H,
m),6.80−6.87(2H,m),7.84−8.00(6H,m). IR(KBr):3433,3087,3004,2949,2871,1604,1565,1520,
1444,1420,1364,1312,1253,11638,1136,1090/cm. [α]D=測定不能 No.1a−30 CDCl3 300MHz 0.95−1.99(14H,m),2.22(1H,m),2.26(2H,t,J=7.2
Hz),2.35(3H,s),3.06(1H,m),3.66(3H,s),4.95
(1H,d,J=6.9Hz),5.15−5.30(2H,m),7.26−7.32(2
H,m),7.97−8.06(6H,m). IR(CHCl3):3374,2996,2946,2868,1763,1728,1591,149
5,1435,1368,1299,1228,1192,1163,1139/cm. [α]D==+12.9゜(CHCl3,c=1.04,26.0℃). No.1a−31 CDCl3 300MHz 0.93−2.01(14H,m),2.19(1H,m),2.31(2H,t,J=7.2
Hz),2.35(3H,s),3.06(1H,m),5.17−5.32(2H,m),
7.25−7.32(2H,m),7.96−8.07(6H,m). IR(CHCl3):3267,3028,2952,2874,1759,1708,1592,149
5,1368,1328,1299,1163,1138,1088,1050,1008/cm. [α]D=+21.7゜(CHCl3,C=0.51,22℃). No.1a−32 CDCl3 300MHz 0.93−1.99(14H,m),2.21(1H,m),2.27(2H,t,J=7.2
Hz),3.05(1H,m),3.67(3H,s),4.92(1H,d,J=6.6H
z),5.15−5.30(2H,m),6.72(1H,s),6.96−7.00(2
H,m),7.86−8.04(6H,m). IR(CHCl3):3374,3276,3018,2946,2686,1725,1605,158
9,1502,1433,1396,1330,1271,1164,1135,1089/cm.
[α]D=+18.6゜(CHCl3,c=1.00,26.0℃). No.1a−33 CDCl3+CD3OD 300MHz 0.98−2.08(14H,m),2.20(1H,m),2.28(2H,t,J=7.2
Hz),2.98(1H,m),5.18−5.32(2H,m),6.92−6.99(2
H,m),7.85−8.02(6H,m). IR(KBr):3385,3248,2948,2876,1717,1601,1505,1430,
1399,1296,1280,1219,1165,1136,1092/cm. [α]D=−16.0゜(CH3OH,c=1.08,26.0℃). mp.208−210℃ No.1a−34 mp.82−83℃ [α]D=+10.6゜(CHCl3,c=1.01,23.
5℃). No.1a−35 mp.80−82℃ [α]D=−1.8゜(CHCl3,c=1.07,22.0
℃). No.1a−36 TLC Rf=0.25(酢酸エチル−n−ヘキサン=1:1(0.3
%酢酸)) No.1a−37 CDCl3 300MHz 0.92−1.96(14H,m),2.21(1H,m),2.27(2H,t,J=7.2
Hz),3.01(1H,m),3.66(3H,s),4.71(1H,d,J=6.6H
z),5.14−5.29(2H,m),7.12(1H,d,J=16.2Hz),7.24
(1H,d,J=16.2Hz),7.28−7.42(3H,m),7.52−7.56
(2H,m),7.62(2H,d,J=8.7Hz),7.85(2H,d,J=8.7H
z). IR(CHCl3):3384,3283,3023,2954,2876,1730,1595,149
4,1317,1163,1147/cm. [α]D=+10.5゜(CHCl3,c=1.01,24℃). mp.116−117℃. No.1a−38 CDCl3 300MHz 0.92−1.99(14H,m),2.17(1H,m),2.32(2H,t,J=7.2
Hz),3.02(1H,m),5.23−5.29(3H,m),7.11(1H,d,J
=16.2Hz),7.23(1H,d,J=16.2Hz),7.28−7.41(3H,
m),7.52−7.55(2H,m),7.61(2H,d,J=8.7Hz),7.86
(2H,d,J=8.7Hz). IR(CHCl3):3515,3384,3270,3022,3015,2957,2876,266
9,1708,1595,1496,1320,1157/cm. [α]D=+27.1゜(CHCl3,c=1.02,24℃). No.1a−39 CDCl3 300MHz 0.92−1.99(14H,m),2.15(1H,m),2.28(2H,t,J=7.4
Hz),3.01(1H,m),3.68(3H,s),4.96(1H,d,J=6.6H
z),5.16−5.32(2H,m),6.60(1H,d,J=12.0Hz),6.74
(1H,d,J=12.0Hz),7.16−7.23(5H,m),7.35(2H,d,J
=8.4Hz),7.72(2H,d,J=8.4Hz). IR(CHCl3):3384,3283,3023,3015,2954,2876,1730,159
5,1493,1324,1163,1147/cm. [α]D=+13.7゜(CHCl3,c=1.00,24℃). No.1a−40 CDCl3 300MHz 0.90−2.16(14H,m),2.12(1H,m),2.34(2H,t,J=7.2
Hz),3.02(1H,m),5.16(1H,d,J=6.9Hz),5.23−5.34
(2H,m),6.60(1H,d,J=12.3Hz),6.74(1H,d,J=12.3
Hz),7.14−7.24(5H,m),7.35(2H,d,J=8.1Hz),7.72
(2H,d,J=8.1Hz). IR(CHCl3):3515,3384,3269,3025,3021,3014,2957,287
6,2668,1709,1595,1322,1162,1147/cm. [α]D=+26.4゜(CHCl3,c=1.00,24℃). No.1a−41 CDCl3 300MHz 0.98−1.99(14H,m),2.17(1H,m),2.32(2H,t,J=7.2
Hz),3.00(1H,m),3.84(3H,s),5.20−5.26(3H,m),
6.90−6.95(2H,m),6.98(1H,d,J=16.2Hz),7.17(1
H,d,J=16.2Hz),7.46−7.49(2H,m),7.58(2H,d,J=
8.4Hz),7.83(2H,d,J=8.4Hz). IR(CHCl3):3258,3018,3002,2950,1709,1590,1509,145
7,1404,1302,1250,1153/cm. [α]D=+30.2゜(CHCl3,c=1.00,23℃). mp.99−100℃ No.1a−42 CDCl3 300MHz 1.01−1.99(14H,m),2.28(2H,t,J=7.2Hz),2.30(1
H,m),3.10(1H,m),3.66(3H,s),5.07(1H,br),5.25
−5.30(2H,m),6.98−7.04(2H,m),7.16(1H,d,J=1
6.2Hz),7.28−7.37(3H,m),7.47−7.50(3H,m). IR(CHCl3):3372,3276,3020,2946,2870,1727,1491,143
3,1331,1152/cm. [α]D=−11.5゜(CHCl3,c=1.07,21.5℃). No.1a−43 CDCl3 300MHz 0.98−2.00(14H,m),2.11−2.36(3H,m),3.12(1H,
m),5.10(1H,d,J=6.6Hz),5.29−5.32(2H,m),6.99
−7.04(2H,m),7.23(1H,d,J=21.6Hz),7.32−7.49
(6H,m). IR(CHCl3):3380,3248,3020,2948,2868,1709,1491,143
0,1329,1151/cm. [α]D=+3.4゜(CHCl3,c=1.03,25℃). No.1a−44 CDCl3 300MHz 1.00−2.00(14H,m),2.13(1H,m),2.29(2H,t,J=7.4
Hz),2.90−3.13(5H,m),3.68(3H,s),4.74(1H,d,J
=6.6Hz),5.15−5.30(2H,m),7.18−7.29(7H,m),7.
76(2H,d,J=8.1Hz). IR(CHCl3):3384,3282,3063,3028,3023,3016,2953,287
6,1730,1599,1496,1319,1157/cm. [α]D=+2.3゜(CHCl3,c=1.00,25℃)。
mp.85.0−86.0℃ No.1a−45 CDCl3 300MHz 0.90−2.05(14H,m),2.09(1H,m),2.35(2H,t,J=6.9
Hz),2.90−3.13(5H,m),5.18(1H,d,J=6.6Hz),5.24
−5.34(2H,m),7.10−7.27(7H,m),7.76(2H,d,J=8.
4Hz). IR(CHCl3):3510,3384,3270,3087,3063,3026,3018,301
4,2955,2876,2670,1708,1599,1496,1318,1157/cm. [α]D=+8.5゜(CHCl3,c=1.01,25℃)。
Hz),2.90−3.13(5H,m),5.18(1H,d,J=6.6Hz),5.24
−5.34(2H,m),7.10−7.27(7H,m),7.76(2H,d,J=8.
4Hz). IR(CHCl3):3510,3384,3270,3087,3063,3026,3018,301
4,2955,2876,2670,1708,1599,1496,1318,1157/cm. [α]D=+8.5゜(CHCl3,c=1.01,25℃)。
No.1a−46 [α]D=+6.8゜(CHCl3,c=1.05,25℃).mp.99−100
℃. No.1a−47 CDCl3 300MHz 0.97−2.01(14H,m),2.14(1H,m),2.36(2H,t,J=7.2
Hz),3.02(1H,m),5.23(1H,d,J=5.4Hz),5.26−5.30
(2H,m),7.37−7.39(3H,m),7.54−7.58(2H,m),7.6
3−7.66(2H,m),7.85−7.88(2H,m). IR(CHCl3):3375,3260,3022,2948,2212,1707,1596,149
7,1396,1322,1160/cm. [α]D=+25.0゜(CHCl3,c=1.02,24℃).mp.117−1
18℃. No.1a−48 CD3OD 300MHz 1.05−1.93(14H,m),2.10−2.15(3H,m),2.96(1H,
m),5.08−5.28(2H,m),7.38−7.40(3H,m),7.554−
7.56(2H,m),7.69(1H,d,J=8.4Hz),7.87(1H,d,J=
8.4Hz). No.1a−49 CDCl3 300MHz 0.96−1.97(14H,m),2.24(1H,m),2.31(2H,t,J=6.9
Hz),3.05(1H,m),3.69(3H,s),5.15(1H,d,J=6.6H
z),5.25−5.27(2H,m),7.40−7.43(3H,m),7.61−7.
64(2H,m),7.85(1H,d,J=8.1Hz),8.07(1H,dd,J=8.
1,1.8Hz),8.58(1H,d,J=1.8Hz). IR(CHCl3):3374,3020,2948,2870,2212,1726,1606,153
0,1493,1437,1345,1167/cm. [α]D=+2.4゜(CHCl3,c=1.03,25℃).mp.77−79
℃. No.1a−50 CDCl3 300MHz 1.00−2.02(14H,m),2.20(1H,m),2.34(2H,t,J=6.6
Hz),3.08(1H,m),5.26−5.29(2H,m),5.41(1H,d,J
=6.9Hz),7.40−7.43(3H,m),7.61−7.64(2H,m),7.
84(1H,d,J=8.1Hz),8.07(1H,dd,J=8.4,1.8Hz),8.5
7(1H,dd,J=1.8Hz). IR(CHCl3):3380,3254,2952,2880,2212,1707,1606,153
1,1493,1409,1344,1166. [α]D=+23.4゜(CHCl3,c=1.00,25℃). No.1a−51 CDCl3 300MHz 0.95−1.98(14H,m),2.23(1H,m),2.30(2H,t,J=7.2
Hz),3.00(1H,m),3.66(3H,s),4.56(2H,br),4.70
(1H,d,J=6.9Hz),5.20−5.29(2H,m),7.15(1H,dd,J
=7.8,1.8Hz),7.23(1H,d,J=1.8Hz),7.36−7.39(3
H,m),7.46(1H,d,J=7.8Hz),7.53−7.56(2H,m). IR(CHCl3):3494,3386,3028,2952,2874,1725,1611,155
9,1497,1422,1317,1162/cm. No.1a−52 CDCl3 300MHz 0.96−2.04(16H,m),2.20(1H,m),2.36(2H,t,J=6.9
Hz),2.99(1H,m),5.17(1H,d,J=6.3Hz),5.28−5.31
(2H,m),7.18(1H,dd,J=9.6,1.8Hz),7.25(1H,m),
7.36−7.39(3H,m),7.46(1H,d,J=7.8Hz),7.52−7.5
6(2H,m). IR(CHCl3):3482,3378,3260,3022,2948,2868,1708,161
2,1495,1422,1317/cm. [α]D=+15.0゜(CHCl3,c=1.00,24℃). No.1a−53 CDCl3 300MHz 1.01−2.05(15H,m),2.31(2H,t,J=7.2Hz),3.10(1
H,m),3.67(3H,s),5.02(1H,br),5.26−5.33(2H,
m),7.18(1H,d,J=4.2Hz),7.36−7.39(3H,m),7.48
(1H,d,J=4.2Hz),7.51−7.55(2H,m). IR(CHCl3):3372,3270,3018,3004,2946,2868,2202,172
6,1486,1433,1336,1154/cm. [α]D=+0.6゜(CHCl3,c=1.11,25℃),[α]436
+17.8゜(CHCl3,c=1.11,25℃). No.1a−54 CDCl3 300MHz 0.99−2.11(14H,m),2.27(1H,m),2.37(2H,t,J=7.5
Hz),3.13(1H,m),5.16(1H,d,J=6.6Hz),5.31−5.35
(2H,m),7.18(1H,d,J=3.6Hz),7.37−7.39(3H,m),
7.50(1H,d,J=3.6Hz),7.52−7.55(2H,m). IR(CHCl3):3484,3370,3246,2948,2868,2202,1708,148
6,1429,1335,1153/cm. [α]D=+17.8゜(CHCl3,c=1.00,24℃).mp.95−96
℃ No.1a−55 CDCl3 300MHz 0.95−1.92(14H,m),2.15(1H,m),2.24(2H,t,J=7.5
Hz),3.00(1H,m),3.66(3H,s),5.10−5.30(3H,m),
7.40−7.60(7H,m),7.70(1H,d,J=7.8Hz),8.08(1H,
d,J=8.1Hz).IR(CHCl3):3356,3020,2948,2868,2210,
1727,1490,1458,1437,1341,1165/cm. [α]D=−58.4゜(CHCl3,c=1.00,26℃).mp.84−85
℃. No.1a−56 CDCl3 300MHz 0.95−1.95(14H,m),2.10(1H,m),2.27(2H,t,J=6.9
Hz),3.00(1H,m),5.17−5.21(2H,m),5.38(1H,d,J
=6.9Hz),7.39−7.60(7H,m),7.70(1H,dd,J=7.8,1.
5Hz),8.07(1H,J=6.6,1.5Hz). IR(CHCl3):3364,3026,2952,2874,2212,1707,1597,149
1,1458,1411,1341,1164/cm. [α]D=−43.1゜(CHCl3,c=1.00,25℃). No.1a−57 CDCl3 300MHz 0.99−1.97(14H,m),2.23−2.30(3H,m),3.01(1H,
m),3.67(3H,s),5.17−5.26(3H,m),7.36−7.38(3
H,m),7.50−7.56(3H,m),7.60(1H,m),7.83(1H,
m),8.05(1H,m). IR(CHCl3):3376,3020,2946,2870,1727,1598,1491,143
7,1412,1330,1245,1163/cm. [α]D=−12.7゜(CHCl3,c=1.00,24℃). No.1a−58 CDCl3 300MHz 0.97−1.98(14H,m),2.20(1H,m),2.33(2H,t,J=6.9
Hz),3.02(1H,m),5.19−5.28(3H,m),7.36−7.38(3
H,m),7.47−7.55(3H,m),7.69(1H,m),7.83(1H,
m),8.04(1H,m). IR(CHCl3):3376,3260,3022,3002,2948,2868,2220,170
8,1598,1490,1455,1412,1327,1162/cm. [α]D=−8.6゜(CHCl3,c=1.01,24℃). No.1a−59 CDCl3 300MHz 0.95−1.99(24H,m),2.20(1H,m),2.28(2H,t,J=7.8
Hz),2.53(1H,s),2.96(1H,m),3.69(3H,s),4.99
(1H,d,J=6.6Hz),5.18−5.20(2H,m),7.53(2H,d,J
=8.4Hz),7.82(2H,d,J=8.4Hz). IR(CHCl3):3585,3376,3002,2936,2852,1725,1591,149
0,1437,1393,1325,1160/cm. [α]D=−8.8゜(CHCl3,c=1.00,24℃). No.1a−60 CDCl3 300MHz 0.96−2.05(24H,m),2.22(1H,m),2.33(2H,m),2.88
(1H,m),5.22−5.26(2H,m),5.30(1H,d,J=5.7Hz),
7.50(2H,d,J=8.7Hz),7.80(2H,d,J=8.7Hz). IR(CHCl3):3376,3260,3022,2936,2852,1710,1592,149
1,1452,1395,1325,1159/cm. [α]D=−8.9゜(CHCl3,c=1.06,24℃), mp.88−91℃ No.1a−61 CDCl3 300MHz 0.95−2.24(23H,m),2.29(2H,m),2.99(1H,m),3.69
(3H,s),4.76(1H,d,J=6.3Hz),5.21−5.24(2H,m),
6.28(1H,m),7.50−7.53(2H,m),7.77−7.80(2H,
m). IR(CHCl3):3374,3270,3018,2942,2868,2196,1726,158
9,1490,1435,1324,1158/cm. [α]D=+7.7゜(CHCl3,c=1.02,24℃),mp.93−95
℃ No.1a−62 CDCl3 300MHz 0.96−2.45(23H,m),2.36(2H,d,J=6.9Hz),2.99(1
H,m),5.24(1H,d,J=6.3Hz),5.24−5.32(2H,m),6.2
8(1H,m),7.50−7.53(2H,m),7.78−7.81(2H,m).IR
(CHCl3):3468,3374,3260,3020,2942,2868,2196,1598,
1490,1455,1398,1322,1157/cm. [α]D=+19.4゜(CHCl3,c=1.03,24℃). No.1a−63 CDCl3 300MHz 0.93−1.95(25H,m),2.16(1H,m),2.29(2H,t,J=7.2
Hz),2.43(2H,t,J=6.9Hz),2.94(1H,m),3.68(3H,
s),4.95(1H,d,J=6.9Hz),5.21−5.24(2H,m),7.49
(2H,d,J=8.7Hz),7.79(2H,J=8.7Hz). IR(CHCl3):3376,3018,2946,2866,2222,1727,1592,145
6,1435,1325,1158/cm. [α]D=+3.7゜(CHCl3,c=1.00,25℃). No.1a−64 CDCl3 300MHz 0.93−1.97(26H,m),2.35(2H,t,J=7.2Hz),2.43(2
H,t,J=7.2Hz),3.00(1H,m),5.08(1H,d,J=6.6Hz),
5.26−5.27(2H,m),7.49(2H,d,J=8.7Hz),7.78(2H,
d,J=8.7Hz). IR(CHCl3):3260,3020,2948,2864,2222,1708,1592,148
9,1456,1397,1324,1156/cm. [α]D=+14.4゜(CHCl3,c=1.00,25℃) mp.70−7
1℃. No.1a−65 CDCl3 300MHz 0.95−1.98(14H,m),2.18(1H,m),2.30(2H,t,J=7.2
Hz),3.00(1H,m),3.67(3H,s),4.83(1H,d,J=6.9H
z),5.22−5.25(2H,m),5.54(1H,br),6.82−6.85(2
H,m),7.42−7.45(2H,m),7.59−7.62(2H,m),7.82−
7.85(2H,m). IR(CHCl3):3576,3374,3018,2946,2868,2208,1725,160
7,1587,1514,1435,1325,1270,1162,1133/cm. [α]D=+9.1゜(CHCl3,c=1.03,24℃).mp.111−11
2℃ No.1a−66 CDCl3 300MHz 0.97−2.03(14H,m),2.15(1H,m),2.35(2H,t,J=7.5
Hz),3.00(1H,m),5.17(1H,d,J=6.6Hz),5.26−5.30
(2H,m),6.82−6.85(2H,m),7.42−7.45(2H,m),7.5
9−7.62(2H,m),7.82−7.85(2H,m). IR(CHCl3):3260,2948,2870,2208,1709,1607,1587,151
4,1396,1325,1270,1162,1133/cm. [α]D=−21.0゜(CHCl3,c=1.00,23℃).mp.161−1
62℃ No.1a−67 CDCl3 300MHz 0.95−1.98(14H,m),2.20(1H,m),2.29(2H,t,J=7.2
Hz),3.01(1H,m),3.67(3H,s),4.82(1H,d,J=6.6H
z),5.19−5.27(2H,m),7.05−7.10(2H,m),7.51−7.
56(2H,m),7.61−7.64(2H,m),7.84−7.87(2H,m), IR(CHCl3):3374,3280,3020,2946,2868,2214,1727,158
9,1509,1435,1327,1233,1161,1134/cm. [α]D=+6.7゜(CHCl3,c=1.01,24℃),mp.84−85
℃ No.1a−68 CDCl3 300MHz 0.96−2.01(14H,m),2.15(1H,m),2.34(2H,t,J=6.9
Hz),3.02(1H,m),5.23−5.27(3H,m),7.04−7.10(2
H,m),7.51−7.56(2H,m),7.61−7.64(2H,m),7.85−
7.88(2H,m). IR(CHCl3):3374,3258,3020,2948,2868,2214,1708,158
9,1509,1455,1398,1322,1156/cm. [α]D=+22.6゜(CHCl3,c=1.02,24℃),mp.135−1
36℃ No.1a−69 CDCl3 300MHz 0.95−1.98(14H,m),2.19(1H,m),2.29(2H,t,J=7.2
Hz),2.39(3H,s),3.01(1H,m),3.69(3H,s),4.80
(1H,d,J=6.6Hz),5.20−5.29(2H,m),7.18(2H,d,J
=8.1Hz),7.44(2H,d,J=8.1Hz),7.62(2H,d,J=8.4H
z),7.84(2H,d,J=8.4Hz). IR(CHCl3):3374,3022,2946,2868,2210,1727,1589,151
1,1436,1323,1161,1133/cm. [α]D=+9.2゜(CHCl3,c=1.02,24℃). mp.116−118℃ No.1a−70 CDCl3 300MHz 1.15−2.00(14H,m),2.13(1H,m),2.33−2.38(5H,
m),3.04(1H,m),5.14(1H,d,J=6.6Hz),5.25−5.30
(2H,m),7.17(2H,d,J=7.8Hz),7.44(2H,d,J=7.8H
z),7.62(2H,d,J=8.4Hz),7.85(2H,d,J=8.4Hz). IR(CHCl3):3380,3260,3020,2948,2868,2210,1708,159
0,1511,1396,1324,1160,1133/cm.[α]D=+24.6゜
(CHCl3,c=1.00,24℃). No.1a−71 CDCl3 300MHz 0.95−1.96(14H,m),2.19(1H,m),2.29(2H,t,J=7.2
Hz),3.00(1H,m),3.20(1H,s),3.65(3H,s),4.81
(1H,d,J=6.6Hz),5.20−5.27(2H,m),7.46−7.54(4
H,m),7.62−7.65(2H,m),7.85−7.88(2H,m). IR(CHCl3):3374,3290,3018,3002,2946,2868,2212,211
0,1726,1591,1507,1435,1401,1324,1161/cm. [α]D=+9.6゜(CHCl3,c=1.01,24℃),mp.136−13
8℃, No.1a−72 CDCl3 300MHz 0.96−2.01(14H,m),2.14(1H,m),2.35(2H,t,J=7.2
Hz),3.05(1H,m),3.20(1H,s),5.16(1H,d,J=7.2H
z),5.26−5.29(2H,m),7.45−7.53(4H,m),7.63(2
H,d,J=8.4Hz),7.87(2H,d,J=8.4Hz). IR(CHCl3):3462,3374,3290,3024,2948,2868,2212,211
0,1708,1591,1508,1455,1401,1321,1274,1160,1132/cm. [α]D=+24.3゜(CHCl3,c=1.03,24℃),mp.96−99
℃ No.1a−73 CDCl3 300MHz 0.95−1.98(14H,m),2.19(1H,m),2.27−2.32(5H,
m),3.01(1H,m),3.67(3H,s),4.80(1H,d,J=6.6H
z),5.20−5.27(2H,m),7.12(2H,m),7.56(2H,m),
7.63(2H,m),7.84(2H,m). IR(CHCl3):3374,3276,3018,2946,2868,2214,1762,173
0,1589,1506,1435,1368,1161/cm. [α]D=+7.8゜(CHCl3,c=1.02,24℃),mp.102−10
4℃ No.1a−74 CDCl3 300MHz 0.95−2.05(14H,m),2.15(1H,m),2.32−2.37(5H,
m),3.02(1H,m),5.14(1H,d,J=6.6Hz),5.26−5.30
(2H,m),7.10−7.13(2H,m),7.54−7.57(2H,m),7.6
2−7.64(2H,m),7.84−7.87(2H,m). IR(CHCl3):3482,3250,3022,2946,2868,2214,1716,170
9,1589,1507,1454,1396,1368,1322,1195,1161/cm. [α]D=+15.0゜(CHCl3,c=1.0,24℃),mp.129−13
1℃ No.1a−75 CDCl3 300MHz 0.95−1.99(14H,m),2.20(1H,m),2.30(2H,t,J=7.2
Hz),3.02(1H,m),3.67(3H,s),3.94(3H,s),4.79
(1H,d,J=6.6Hz),5.19−5.29(2H,m),7.60−7.63(2
H,m),7.65−7.67(2H,m),7.86−7.89(2H,m),8.04−
8.06(2H,m). IR(CHCl3):3378,3018,2946,2880,1720,1604,1435,130
7,1276,1161,1106/cm. [α]D=+7.3゜(CHCl3,c=1.01,25℃),mp.132−13
3℃ No.1a−76 CDCl3+CD3OD 300MHz 1.04−2.05(14H,m),2.19(1H,m),2.32(2H,t,J=6.9
Hz),2.93(1H,m),5.27−5.31(2H,m),7.60−7.63(2
H,m),7.65−7.68(2H,m),7.86−7.89(2H,m),8.05−
8.07(2H,m). IR(CHCl3):3402,3299,2955,2876,2665,2549,1455,142
2,1313,1281,1164/cm. [α]D=−21.1゜(CH30H,c=1.03,23℃),mp.227−2
29(dec.) No.1a−77 CDCl3 300MHz 0.96−1.99(14H,m),2.20(1H,m),2.30(2H,t,J=7.2
Hz),3.02(1H,m),3.68(3H,s),4.88(1H,d,J=6.3H
z),5.19−5.29(2H,m),7.67−7.72(4H,m),7.89−7.
91(2H,m),8.24−8.27(2H,m). IR(CHCl3):3376,3276,3020,2946,2870,2214,1726,159
4,1519,1455,1435,1389,1344,1161/cm. [α]D=+7.7゜(CHCl3,c=1.02),mp.87−89℃ No.1a−78 CDCl3 300MHz 0.98−2.00(14H,m),2.18(1H,m),2.34(2H,t,J=7.2
Hz),3.02(1H,m),5.24−5.28(2H,m),5.32(1H,d,J
=5.7Hz),7.67−7.72(4H,m),7.89−7.92(2H,m),8.
23−8.26(2H,m). IR(CHCl3):3374,3260,2948,2214,1708,1595,1344,116
0/cm. [α]D=+23.3゜(CHCl3,c=1.00), mp.102−103℃ No.1a−79 CDCl3 300MHz 0.93−2.02(14H,m),2.13(1H,m),2.36(2H,t,J=7.1
Hz),3.05(1H,m),3.84(3H,s),5.18(1H,br),5.27
−5.31(2H,m),6.88−6.91(2H,m),7.48−7.50(2H,
m),7.60−7.63(2H,m),7.83−7.85(2H,m). IR(CHCl3):3380,3252,3020,2950,2868,2208,1708,158
9,1511,1457,1396,1321,1286,1160/cm. [α]D=+26.7゜(CHCl3,C=1.00).mp.75−77℃ No.1a−80 CDCl3 300MHz 0.96−1.99(14H,m),2.21(1H,m),2.30(2H,t,J=7.8
Hz),3.02(1H,m),3.68(3H,s),4.80(1H,d,J=6.6H
z),5.19−5.28(2H,m),7.51−7.77(5H,m),7.87−7.
90(2H,m),8.13(1H,m). IR(CHCl3):3374,3270,3018,2946,2868,2216,1726,160
7,1567,1527,1495,1456,1436,1344,1296,1161/cm. [α]D=+7.4゜(CHCl3,c=1.00,22℃),mp.68−70
℃ No.1a−81 CDCl3 300MHz 0.97−2.01(14H,m),2.16(1H,m),2.34(2H,t,J=7.2
Hz),3.01(1H,m),5.22−5.28(3H,m),7.51(1H,m),
7.65(1H,m)7.70−7.76(3H,m),7.88−7.91(2H,m),
8.12(1H,dd,J=6.9Hz,1.5Hz). IR(CHCl3):3480,3382,3262,3026,2952,2872,2218,170
8,1607,1567,1526,1396,1343,1225,1160/cm. [α]D=+22.0゜(CHCl3,c=1.00),mp.92−94℃ No.1a−82 CDCl3 300MHz 0.95−1.98(14H,m),2.20(1H,m),2.29(2H,t,J=7.2
Hz),3.01(1H,m),3.67(3H,s),4.30(2H,br),4.79
(1H,d,J=6.9Hz),5.20−5.29(2H,m),6.71−6.76(2
H,m),7.18(1H,m),7.37(1H,dd,J=7.8,1.2Hz),7.61
−7.65(2H,m),7.83−7.87(2H,m). IR(CHCl3):3376,3020,2946,2868,2202,1725,1613,158
9,1484,1454,1315,1253,1161/cm. [α]D=+8.9゜(CHCl3,c=1.00,22℃).mp.68−70
℃ No.1a−83 CDCl3 300MHz 0.97−1.99(14H,m),2.17(1H,m),2.33(2H,t,J=6.9
Hz),2.99(1H,m),5.20−5.28(2H,m),5.37(1H,d,J
=6.9Hz),6.45(2H,br),6.71−6.76(2H,m),7.19(1
H,dd,J=7.8,6.6Hz),7.37(1H,m),7.62(2H,d,J=8.4
Hz),7.85(2H,d,J=8.4Hz). IR(CHCl3):3478,3378,3260,3022,2950,2868,2204,170
8,1613,1589,1484,1454,1396,1316,1160/cm. [α]D=+17.1゜(CHCl3,c=1.01). No.1a−84 CDCl3 300MHz 1.00−2.08(14H,m),2.21(1H,m),2.37(2H,t,J=6.9
Hz),3.06(1H,m),3.86(3H,s),5.29−5.33(2H,m),
5.45(1H,d,J=6.6Hz),6.91−6.94(2H,m),7.56−7.5
9(2H,m),7.81(1H,d,J=8.1Hz),8.04(1H,d.d,J=8.
1&1.8Hz),8.57(1H,d,t,J=2.1Hz). IR(CHCl3):3492,3254,3028,2954,2202,1708,1597,151
2,1344,1291,1250/cm. [α]D=+27.4゜(CHCl3,C=0.53,23℃). No.1a−85 CDCl3 300MHz 0.96−2.05(14H,m),2.20(1H,m),2.35(2H,t,J=6.9
Hz),2.99(1H,m),3.84(3H,s),5.22−5.31(3H,m),
6.89(2H,d,J=8.7Hz),7.19(1H,brs),7.29(1H,br
s),7.45−7.50(3H,m). IR(CHCl3):3478,3378,3020,2950,2868,2202,1708,160
6,1511,1421,1311,1287,1248,1155/cm. [α]D=+17.1゜(CHCl3,C=1.00,23℃). No.1a−86 CDCl3 300MHz 1.03−2.05(14H,m),2.21(1H,m),2.37(2H,t,J=6.9
Hz),3.04(1H,m),5.29−5.33(2H,m),5.57(1H,d,J
=6.3Hz),6.84−6.87(2H,m),7.50−7.53(2H,m),7.
79(1H,d,J=8.1Hz),8.03(1H,d,d,J=1.5and8.1Hz),
8.57(1H,d,J=1.5Hz). IR(CHCl3):3250,3024,2950,2868,2200,1707,1515,134
4,1271,1166,1143/cm. [α]D=+21.2゜(CHCl3,C=0.26,22℃). No.1a−87 CD3OD 300MHz 1.04−2.00(14H,m),2.18(1H,m),2.26(2H,t,J=5.4
Hz),2.93(1H,m),5.19−5.24(2H,m),6.77−6.80(2
H,m),7.05(1H,d.d,J=2.1and8.1Hz),7.22(1H,d,J=
2.1Hz),7.38−7.42(3H,m). IR(CHCl3):3377,2952,2873,2204,1705,1607,1515,142
5,1312,1267,1222,1153/cm. [α]D=−15.6゜(CH3OH,C=1.02,22℃). No.1a−88 CDCl3 300MHz 0.90−1.96(14H,m),2.22−2.31(3H,m),2.95(1H,
m),3.65(3H,s),4.87(1H,d,J=6.6Hz),5.13−5.28
(2H,m),7.46−7.62(3H,m),7.82−7.89(4H,m),7.9
0−7.92(2H,m),8.42(1H,brs). IR(CHCl3):3376,3016,2946,2868,1720,1677,1592,151
4,1498,1429,1376,1314,1241,1156,1094/cm. [α]D=−10.7゜(CHCl3,c=1.04,22.0℃) mp.134
−136℃ No.1a−89 CDCl3+CD3OD 300MHz 0.96−2.08(14H,m),2.23(1H,m),2.28(2H,t,J=7.2
Hz),2.89(1H,m),5.20−5.32(2H,m),7.46−7.62(3
H,m),7.82−7.97(6H,m). IR(KBr):3272,3007,2952,2874,1708,1660,1592,1527,
1498,1433,1400,1317,1260,1152,1094/cm. [α]D=−24.4゜(CH3OH,c=1.02,25.0℃)。
℃. No.1a−47 CDCl3 300MHz 0.97−2.01(14H,m),2.14(1H,m),2.36(2H,t,J=7.2
Hz),3.02(1H,m),5.23(1H,d,J=5.4Hz),5.26−5.30
(2H,m),7.37−7.39(3H,m),7.54−7.58(2H,m),7.6
3−7.66(2H,m),7.85−7.88(2H,m). IR(CHCl3):3375,3260,3022,2948,2212,1707,1596,149
7,1396,1322,1160/cm. [α]D=+25.0゜(CHCl3,c=1.02,24℃).mp.117−1
18℃. No.1a−48 CD3OD 300MHz 1.05−1.93(14H,m),2.10−2.15(3H,m),2.96(1H,
m),5.08−5.28(2H,m),7.38−7.40(3H,m),7.554−
7.56(2H,m),7.69(1H,d,J=8.4Hz),7.87(1H,d,J=
8.4Hz). No.1a−49 CDCl3 300MHz 0.96−1.97(14H,m),2.24(1H,m),2.31(2H,t,J=6.9
Hz),3.05(1H,m),3.69(3H,s),5.15(1H,d,J=6.6H
z),5.25−5.27(2H,m),7.40−7.43(3H,m),7.61−7.
64(2H,m),7.85(1H,d,J=8.1Hz),8.07(1H,dd,J=8.
1,1.8Hz),8.58(1H,d,J=1.8Hz). IR(CHCl3):3374,3020,2948,2870,2212,1726,1606,153
0,1493,1437,1345,1167/cm. [α]D=+2.4゜(CHCl3,c=1.03,25℃).mp.77−79
℃. No.1a−50 CDCl3 300MHz 1.00−2.02(14H,m),2.20(1H,m),2.34(2H,t,J=6.6
Hz),3.08(1H,m),5.26−5.29(2H,m),5.41(1H,d,J
=6.9Hz),7.40−7.43(3H,m),7.61−7.64(2H,m),7.
84(1H,d,J=8.1Hz),8.07(1H,dd,J=8.4,1.8Hz),8.5
7(1H,dd,J=1.8Hz). IR(CHCl3):3380,3254,2952,2880,2212,1707,1606,153
1,1493,1409,1344,1166. [α]D=+23.4゜(CHCl3,c=1.00,25℃). No.1a−51 CDCl3 300MHz 0.95−1.98(14H,m),2.23(1H,m),2.30(2H,t,J=7.2
Hz),3.00(1H,m),3.66(3H,s),4.56(2H,br),4.70
(1H,d,J=6.9Hz),5.20−5.29(2H,m),7.15(1H,dd,J
=7.8,1.8Hz),7.23(1H,d,J=1.8Hz),7.36−7.39(3
H,m),7.46(1H,d,J=7.8Hz),7.53−7.56(2H,m). IR(CHCl3):3494,3386,3028,2952,2874,1725,1611,155
9,1497,1422,1317,1162/cm. No.1a−52 CDCl3 300MHz 0.96−2.04(16H,m),2.20(1H,m),2.36(2H,t,J=6.9
Hz),2.99(1H,m),5.17(1H,d,J=6.3Hz),5.28−5.31
(2H,m),7.18(1H,dd,J=9.6,1.8Hz),7.25(1H,m),
7.36−7.39(3H,m),7.46(1H,d,J=7.8Hz),7.52−7.5
6(2H,m). IR(CHCl3):3482,3378,3260,3022,2948,2868,1708,161
2,1495,1422,1317/cm. [α]D=+15.0゜(CHCl3,c=1.00,24℃). No.1a−53 CDCl3 300MHz 1.01−2.05(15H,m),2.31(2H,t,J=7.2Hz),3.10(1
H,m),3.67(3H,s),5.02(1H,br),5.26−5.33(2H,
m),7.18(1H,d,J=4.2Hz),7.36−7.39(3H,m),7.48
(1H,d,J=4.2Hz),7.51−7.55(2H,m). IR(CHCl3):3372,3270,3018,3004,2946,2868,2202,172
6,1486,1433,1336,1154/cm. [α]D=+0.6゜(CHCl3,c=1.11,25℃),[α]436
+17.8゜(CHCl3,c=1.11,25℃). No.1a−54 CDCl3 300MHz 0.99−2.11(14H,m),2.27(1H,m),2.37(2H,t,J=7.5
Hz),3.13(1H,m),5.16(1H,d,J=6.6Hz),5.31−5.35
(2H,m),7.18(1H,d,J=3.6Hz),7.37−7.39(3H,m),
7.50(1H,d,J=3.6Hz),7.52−7.55(2H,m). IR(CHCl3):3484,3370,3246,2948,2868,2202,1708,148
6,1429,1335,1153/cm. [α]D=+17.8゜(CHCl3,c=1.00,24℃).mp.95−96
℃ No.1a−55 CDCl3 300MHz 0.95−1.92(14H,m),2.15(1H,m),2.24(2H,t,J=7.5
Hz),3.00(1H,m),3.66(3H,s),5.10−5.30(3H,m),
7.40−7.60(7H,m),7.70(1H,d,J=7.8Hz),8.08(1H,
d,J=8.1Hz).IR(CHCl3):3356,3020,2948,2868,2210,
1727,1490,1458,1437,1341,1165/cm. [α]D=−58.4゜(CHCl3,c=1.00,26℃).mp.84−85
℃. No.1a−56 CDCl3 300MHz 0.95−1.95(14H,m),2.10(1H,m),2.27(2H,t,J=6.9
Hz),3.00(1H,m),5.17−5.21(2H,m),5.38(1H,d,J
=6.9Hz),7.39−7.60(7H,m),7.70(1H,dd,J=7.8,1.
5Hz),8.07(1H,J=6.6,1.5Hz). IR(CHCl3):3364,3026,2952,2874,2212,1707,1597,149
1,1458,1411,1341,1164/cm. [α]D=−43.1゜(CHCl3,c=1.00,25℃). No.1a−57 CDCl3 300MHz 0.99−1.97(14H,m),2.23−2.30(3H,m),3.01(1H,
m),3.67(3H,s),5.17−5.26(3H,m),7.36−7.38(3
H,m),7.50−7.56(3H,m),7.60(1H,m),7.83(1H,
m),8.05(1H,m). IR(CHCl3):3376,3020,2946,2870,1727,1598,1491,143
7,1412,1330,1245,1163/cm. [α]D=−12.7゜(CHCl3,c=1.00,24℃). No.1a−58 CDCl3 300MHz 0.97−1.98(14H,m),2.20(1H,m),2.33(2H,t,J=6.9
Hz),3.02(1H,m),5.19−5.28(3H,m),7.36−7.38(3
H,m),7.47−7.55(3H,m),7.69(1H,m),7.83(1H,
m),8.04(1H,m). IR(CHCl3):3376,3260,3022,3002,2948,2868,2220,170
8,1598,1490,1455,1412,1327,1162/cm. [α]D=−8.6゜(CHCl3,c=1.01,24℃). No.1a−59 CDCl3 300MHz 0.95−1.99(24H,m),2.20(1H,m),2.28(2H,t,J=7.8
Hz),2.53(1H,s),2.96(1H,m),3.69(3H,s),4.99
(1H,d,J=6.6Hz),5.18−5.20(2H,m),7.53(2H,d,J
=8.4Hz),7.82(2H,d,J=8.4Hz). IR(CHCl3):3585,3376,3002,2936,2852,1725,1591,149
0,1437,1393,1325,1160/cm. [α]D=−8.8゜(CHCl3,c=1.00,24℃). No.1a−60 CDCl3 300MHz 0.96−2.05(24H,m),2.22(1H,m),2.33(2H,m),2.88
(1H,m),5.22−5.26(2H,m),5.30(1H,d,J=5.7Hz),
7.50(2H,d,J=8.7Hz),7.80(2H,d,J=8.7Hz). IR(CHCl3):3376,3260,3022,2936,2852,1710,1592,149
1,1452,1395,1325,1159/cm. [α]D=−8.9゜(CHCl3,c=1.06,24℃), mp.88−91℃ No.1a−61 CDCl3 300MHz 0.95−2.24(23H,m),2.29(2H,m),2.99(1H,m),3.69
(3H,s),4.76(1H,d,J=6.3Hz),5.21−5.24(2H,m),
6.28(1H,m),7.50−7.53(2H,m),7.77−7.80(2H,
m). IR(CHCl3):3374,3270,3018,2942,2868,2196,1726,158
9,1490,1435,1324,1158/cm. [α]D=+7.7゜(CHCl3,c=1.02,24℃),mp.93−95
℃ No.1a−62 CDCl3 300MHz 0.96−2.45(23H,m),2.36(2H,d,J=6.9Hz),2.99(1
H,m),5.24(1H,d,J=6.3Hz),5.24−5.32(2H,m),6.2
8(1H,m),7.50−7.53(2H,m),7.78−7.81(2H,m).IR
(CHCl3):3468,3374,3260,3020,2942,2868,2196,1598,
1490,1455,1398,1322,1157/cm. [α]D=+19.4゜(CHCl3,c=1.03,24℃). No.1a−63 CDCl3 300MHz 0.93−1.95(25H,m),2.16(1H,m),2.29(2H,t,J=7.2
Hz),2.43(2H,t,J=6.9Hz),2.94(1H,m),3.68(3H,
s),4.95(1H,d,J=6.9Hz),5.21−5.24(2H,m),7.49
(2H,d,J=8.7Hz),7.79(2H,J=8.7Hz). IR(CHCl3):3376,3018,2946,2866,2222,1727,1592,145
6,1435,1325,1158/cm. [α]D=+3.7゜(CHCl3,c=1.00,25℃). No.1a−64 CDCl3 300MHz 0.93−1.97(26H,m),2.35(2H,t,J=7.2Hz),2.43(2
H,t,J=7.2Hz),3.00(1H,m),5.08(1H,d,J=6.6Hz),
5.26−5.27(2H,m),7.49(2H,d,J=8.7Hz),7.78(2H,
d,J=8.7Hz). IR(CHCl3):3260,3020,2948,2864,2222,1708,1592,148
9,1456,1397,1324,1156/cm. [α]D=+14.4゜(CHCl3,c=1.00,25℃) mp.70−7
1℃. No.1a−65 CDCl3 300MHz 0.95−1.98(14H,m),2.18(1H,m),2.30(2H,t,J=7.2
Hz),3.00(1H,m),3.67(3H,s),4.83(1H,d,J=6.9H
z),5.22−5.25(2H,m),5.54(1H,br),6.82−6.85(2
H,m),7.42−7.45(2H,m),7.59−7.62(2H,m),7.82−
7.85(2H,m). IR(CHCl3):3576,3374,3018,2946,2868,2208,1725,160
7,1587,1514,1435,1325,1270,1162,1133/cm. [α]D=+9.1゜(CHCl3,c=1.03,24℃).mp.111−11
2℃ No.1a−66 CDCl3 300MHz 0.97−2.03(14H,m),2.15(1H,m),2.35(2H,t,J=7.5
Hz),3.00(1H,m),5.17(1H,d,J=6.6Hz),5.26−5.30
(2H,m),6.82−6.85(2H,m),7.42−7.45(2H,m),7.5
9−7.62(2H,m),7.82−7.85(2H,m). IR(CHCl3):3260,2948,2870,2208,1709,1607,1587,151
4,1396,1325,1270,1162,1133/cm. [α]D=−21.0゜(CHCl3,c=1.00,23℃).mp.161−1
62℃ No.1a−67 CDCl3 300MHz 0.95−1.98(14H,m),2.20(1H,m),2.29(2H,t,J=7.2
Hz),3.01(1H,m),3.67(3H,s),4.82(1H,d,J=6.6H
z),5.19−5.27(2H,m),7.05−7.10(2H,m),7.51−7.
56(2H,m),7.61−7.64(2H,m),7.84−7.87(2H,m), IR(CHCl3):3374,3280,3020,2946,2868,2214,1727,158
9,1509,1435,1327,1233,1161,1134/cm. [α]D=+6.7゜(CHCl3,c=1.01,24℃),mp.84−85
℃ No.1a−68 CDCl3 300MHz 0.96−2.01(14H,m),2.15(1H,m),2.34(2H,t,J=6.9
Hz),3.02(1H,m),5.23−5.27(3H,m),7.04−7.10(2
H,m),7.51−7.56(2H,m),7.61−7.64(2H,m),7.85−
7.88(2H,m). IR(CHCl3):3374,3258,3020,2948,2868,2214,1708,158
9,1509,1455,1398,1322,1156/cm. [α]D=+22.6゜(CHCl3,c=1.02,24℃),mp.135−1
36℃ No.1a−69 CDCl3 300MHz 0.95−1.98(14H,m),2.19(1H,m),2.29(2H,t,J=7.2
Hz),2.39(3H,s),3.01(1H,m),3.69(3H,s),4.80
(1H,d,J=6.6Hz),5.20−5.29(2H,m),7.18(2H,d,J
=8.1Hz),7.44(2H,d,J=8.1Hz),7.62(2H,d,J=8.4H
z),7.84(2H,d,J=8.4Hz). IR(CHCl3):3374,3022,2946,2868,2210,1727,1589,151
1,1436,1323,1161,1133/cm. [α]D=+9.2゜(CHCl3,c=1.02,24℃). mp.116−118℃ No.1a−70 CDCl3 300MHz 1.15−2.00(14H,m),2.13(1H,m),2.33−2.38(5H,
m),3.04(1H,m),5.14(1H,d,J=6.6Hz),5.25−5.30
(2H,m),7.17(2H,d,J=7.8Hz),7.44(2H,d,J=7.8H
z),7.62(2H,d,J=8.4Hz),7.85(2H,d,J=8.4Hz). IR(CHCl3):3380,3260,3020,2948,2868,2210,1708,159
0,1511,1396,1324,1160,1133/cm.[α]D=+24.6゜
(CHCl3,c=1.00,24℃). No.1a−71 CDCl3 300MHz 0.95−1.96(14H,m),2.19(1H,m),2.29(2H,t,J=7.2
Hz),3.00(1H,m),3.20(1H,s),3.65(3H,s),4.81
(1H,d,J=6.6Hz),5.20−5.27(2H,m),7.46−7.54(4
H,m),7.62−7.65(2H,m),7.85−7.88(2H,m). IR(CHCl3):3374,3290,3018,3002,2946,2868,2212,211
0,1726,1591,1507,1435,1401,1324,1161/cm. [α]D=+9.6゜(CHCl3,c=1.01,24℃),mp.136−13
8℃, No.1a−72 CDCl3 300MHz 0.96−2.01(14H,m),2.14(1H,m),2.35(2H,t,J=7.2
Hz),3.05(1H,m),3.20(1H,s),5.16(1H,d,J=7.2H
z),5.26−5.29(2H,m),7.45−7.53(4H,m),7.63(2
H,d,J=8.4Hz),7.87(2H,d,J=8.4Hz). IR(CHCl3):3462,3374,3290,3024,2948,2868,2212,211
0,1708,1591,1508,1455,1401,1321,1274,1160,1132/cm. [α]D=+24.3゜(CHCl3,c=1.03,24℃),mp.96−99
℃ No.1a−73 CDCl3 300MHz 0.95−1.98(14H,m),2.19(1H,m),2.27−2.32(5H,
m),3.01(1H,m),3.67(3H,s),4.80(1H,d,J=6.6H
z),5.20−5.27(2H,m),7.12(2H,m),7.56(2H,m),
7.63(2H,m),7.84(2H,m). IR(CHCl3):3374,3276,3018,2946,2868,2214,1762,173
0,1589,1506,1435,1368,1161/cm. [α]D=+7.8゜(CHCl3,c=1.02,24℃),mp.102−10
4℃ No.1a−74 CDCl3 300MHz 0.95−2.05(14H,m),2.15(1H,m),2.32−2.37(5H,
m),3.02(1H,m),5.14(1H,d,J=6.6Hz),5.26−5.30
(2H,m),7.10−7.13(2H,m),7.54−7.57(2H,m),7.6
2−7.64(2H,m),7.84−7.87(2H,m). IR(CHCl3):3482,3250,3022,2946,2868,2214,1716,170
9,1589,1507,1454,1396,1368,1322,1195,1161/cm. [α]D=+15.0゜(CHCl3,c=1.0,24℃),mp.129−13
1℃ No.1a−75 CDCl3 300MHz 0.95−1.99(14H,m),2.20(1H,m),2.30(2H,t,J=7.2
Hz),3.02(1H,m),3.67(3H,s),3.94(3H,s),4.79
(1H,d,J=6.6Hz),5.19−5.29(2H,m),7.60−7.63(2
H,m),7.65−7.67(2H,m),7.86−7.89(2H,m),8.04−
8.06(2H,m). IR(CHCl3):3378,3018,2946,2880,1720,1604,1435,130
7,1276,1161,1106/cm. [α]D=+7.3゜(CHCl3,c=1.01,25℃),mp.132−13
3℃ No.1a−76 CDCl3+CD3OD 300MHz 1.04−2.05(14H,m),2.19(1H,m),2.32(2H,t,J=6.9
Hz),2.93(1H,m),5.27−5.31(2H,m),7.60−7.63(2
H,m),7.65−7.68(2H,m),7.86−7.89(2H,m),8.05−
8.07(2H,m). IR(CHCl3):3402,3299,2955,2876,2665,2549,1455,142
2,1313,1281,1164/cm. [α]D=−21.1゜(CH30H,c=1.03,23℃),mp.227−2
29(dec.) No.1a−77 CDCl3 300MHz 0.96−1.99(14H,m),2.20(1H,m),2.30(2H,t,J=7.2
Hz),3.02(1H,m),3.68(3H,s),4.88(1H,d,J=6.3H
z),5.19−5.29(2H,m),7.67−7.72(4H,m),7.89−7.
91(2H,m),8.24−8.27(2H,m). IR(CHCl3):3376,3276,3020,2946,2870,2214,1726,159
4,1519,1455,1435,1389,1344,1161/cm. [α]D=+7.7゜(CHCl3,c=1.02),mp.87−89℃ No.1a−78 CDCl3 300MHz 0.98−2.00(14H,m),2.18(1H,m),2.34(2H,t,J=7.2
Hz),3.02(1H,m),5.24−5.28(2H,m),5.32(1H,d,J
=5.7Hz),7.67−7.72(4H,m),7.89−7.92(2H,m),8.
23−8.26(2H,m). IR(CHCl3):3374,3260,2948,2214,1708,1595,1344,116
0/cm. [α]D=+23.3゜(CHCl3,c=1.00), mp.102−103℃ No.1a−79 CDCl3 300MHz 0.93−2.02(14H,m),2.13(1H,m),2.36(2H,t,J=7.1
Hz),3.05(1H,m),3.84(3H,s),5.18(1H,br),5.27
−5.31(2H,m),6.88−6.91(2H,m),7.48−7.50(2H,
m),7.60−7.63(2H,m),7.83−7.85(2H,m). IR(CHCl3):3380,3252,3020,2950,2868,2208,1708,158
9,1511,1457,1396,1321,1286,1160/cm. [α]D=+26.7゜(CHCl3,C=1.00).mp.75−77℃ No.1a−80 CDCl3 300MHz 0.96−1.99(14H,m),2.21(1H,m),2.30(2H,t,J=7.8
Hz),3.02(1H,m),3.68(3H,s),4.80(1H,d,J=6.6H
z),5.19−5.28(2H,m),7.51−7.77(5H,m),7.87−7.
90(2H,m),8.13(1H,m). IR(CHCl3):3374,3270,3018,2946,2868,2216,1726,160
7,1567,1527,1495,1456,1436,1344,1296,1161/cm. [α]D=+7.4゜(CHCl3,c=1.00,22℃),mp.68−70
℃ No.1a−81 CDCl3 300MHz 0.97−2.01(14H,m),2.16(1H,m),2.34(2H,t,J=7.2
Hz),3.01(1H,m),5.22−5.28(3H,m),7.51(1H,m),
7.65(1H,m)7.70−7.76(3H,m),7.88−7.91(2H,m),
8.12(1H,dd,J=6.9Hz,1.5Hz). IR(CHCl3):3480,3382,3262,3026,2952,2872,2218,170
8,1607,1567,1526,1396,1343,1225,1160/cm. [α]D=+22.0゜(CHCl3,c=1.00),mp.92−94℃ No.1a−82 CDCl3 300MHz 0.95−1.98(14H,m),2.20(1H,m),2.29(2H,t,J=7.2
Hz),3.01(1H,m),3.67(3H,s),4.30(2H,br),4.79
(1H,d,J=6.9Hz),5.20−5.29(2H,m),6.71−6.76(2
H,m),7.18(1H,m),7.37(1H,dd,J=7.8,1.2Hz),7.61
−7.65(2H,m),7.83−7.87(2H,m). IR(CHCl3):3376,3020,2946,2868,2202,1725,1613,158
9,1484,1454,1315,1253,1161/cm. [α]D=+8.9゜(CHCl3,c=1.00,22℃).mp.68−70
℃ No.1a−83 CDCl3 300MHz 0.97−1.99(14H,m),2.17(1H,m),2.33(2H,t,J=6.9
Hz),2.99(1H,m),5.20−5.28(2H,m),5.37(1H,d,J
=6.9Hz),6.45(2H,br),6.71−6.76(2H,m),7.19(1
H,dd,J=7.8,6.6Hz),7.37(1H,m),7.62(2H,d,J=8.4
Hz),7.85(2H,d,J=8.4Hz). IR(CHCl3):3478,3378,3260,3022,2950,2868,2204,170
8,1613,1589,1484,1454,1396,1316,1160/cm. [α]D=+17.1゜(CHCl3,c=1.01). No.1a−84 CDCl3 300MHz 1.00−2.08(14H,m),2.21(1H,m),2.37(2H,t,J=6.9
Hz),3.06(1H,m),3.86(3H,s),5.29−5.33(2H,m),
5.45(1H,d,J=6.6Hz),6.91−6.94(2H,m),7.56−7.5
9(2H,m),7.81(1H,d,J=8.1Hz),8.04(1H,d.d,J=8.
1&1.8Hz),8.57(1H,d,t,J=2.1Hz). IR(CHCl3):3492,3254,3028,2954,2202,1708,1597,151
2,1344,1291,1250/cm. [α]D=+27.4゜(CHCl3,C=0.53,23℃). No.1a−85 CDCl3 300MHz 0.96−2.05(14H,m),2.20(1H,m),2.35(2H,t,J=6.9
Hz),2.99(1H,m),3.84(3H,s),5.22−5.31(3H,m),
6.89(2H,d,J=8.7Hz),7.19(1H,brs),7.29(1H,br
s),7.45−7.50(3H,m). IR(CHCl3):3478,3378,3020,2950,2868,2202,1708,160
6,1511,1421,1311,1287,1248,1155/cm. [α]D=+17.1゜(CHCl3,C=1.00,23℃). No.1a−86 CDCl3 300MHz 1.03−2.05(14H,m),2.21(1H,m),2.37(2H,t,J=6.9
Hz),3.04(1H,m),5.29−5.33(2H,m),5.57(1H,d,J
=6.3Hz),6.84−6.87(2H,m),7.50−7.53(2H,m),7.
79(1H,d,J=8.1Hz),8.03(1H,d,d,J=1.5and8.1Hz),
8.57(1H,d,J=1.5Hz). IR(CHCl3):3250,3024,2950,2868,2200,1707,1515,134
4,1271,1166,1143/cm. [α]D=+21.2゜(CHCl3,C=0.26,22℃). No.1a−87 CD3OD 300MHz 1.04−2.00(14H,m),2.18(1H,m),2.26(2H,t,J=5.4
Hz),2.93(1H,m),5.19−5.24(2H,m),6.77−6.80(2
H,m),7.05(1H,d.d,J=2.1and8.1Hz),7.22(1H,d,J=
2.1Hz),7.38−7.42(3H,m). IR(CHCl3):3377,2952,2873,2204,1705,1607,1515,142
5,1312,1267,1222,1153/cm. [α]D=−15.6゜(CH3OH,C=1.02,22℃). No.1a−88 CDCl3 300MHz 0.90−1.96(14H,m),2.22−2.31(3H,m),2.95(1H,
m),3.65(3H,s),4.87(1H,d,J=6.6Hz),5.13−5.28
(2H,m),7.46−7.62(3H,m),7.82−7.89(4H,m),7.9
0−7.92(2H,m),8.42(1H,brs). IR(CHCl3):3376,3016,2946,2868,1720,1677,1592,151
4,1498,1429,1376,1314,1241,1156,1094/cm. [α]D=−10.7゜(CHCl3,c=1.04,22.0℃) mp.134
−136℃ No.1a−89 CDCl3+CD3OD 300MHz 0.96−2.08(14H,m),2.23(1H,m),2.28(2H,t,J=7.2
Hz),2.89(1H,m),5.20−5.32(2H,m),7.46−7.62(3
H,m),7.82−7.97(6H,m). IR(KBr):3272,3007,2952,2874,1708,1660,1592,1527,
1498,1433,1400,1317,1260,1152,1094/cm. [α]D=−24.4゜(CH3OH,c=1.02,25.0℃)。
No.1a−90 CDCl3 300MHz 0.89−1.96(14H,m),2.23−2.33(3H,m),2.92(1H,
m),3.67(3H,s),4.85(1H,d,J=6.3Hz),5.10−5.25
(2H,m),7.81−7.90(4H,m),8.10−8.18(2H,m),8.3
1−8.40(2H,m),8.77(1H,s). IR(CHCl3):3372,3018,2946,2868,1718,1685,1592,152
7,1436,1397,1346,1318,1256,1154,1099/cm. [α]D=−16.1゜(CHCl3,c=1.00,23.0℃)。
m),3.67(3H,s),4.85(1H,d,J=6.3Hz),5.10−5.25
(2H,m),7.81−7.90(4H,m),8.10−8.18(2H,m),8.3
1−8.40(2H,m),8.77(1H,s). IR(CHCl3):3372,3018,2946,2868,1718,1685,1592,152
7,1436,1397,1346,1318,1256,1154,1099/cm. [α]D=−16.1゜(CHCl3,c=1.00,23.0℃)。
No.1a−91 CDCl3+CD3OD 300MHz 0.94−2.02(14H,m),2.18−2.36(3H,m),2.87(1H,
m),5.15−5.30(2H,m),7.82−7.92(4H,m),8.09−8.
16(2H,m),8.30−8.37(2H,m). IR(KBr):3284,3112,3006,2952,2874,1707,1593,1528,
1498,1399,1348,1320,1259,1153,1093/cm. [α]D=−26.3゜(CH3OH,c=1.01,22℃). No.1a−92 CDCl3 300MHz 0.93−1.95(14H,m),2.22−2.31(3H,m),2.98(1H,
m),3.68(3H,s),5.07(1H,d,J=6.9Hz),5.10−5.24
(2H,m),7.18(1H,m),7.35−7.43(2H,m),7.70(2H,
d,J=7.8Hz),7.88−8.05(4H,m),8.50(1H,brs). IR(CHCl3):3382,3008,2952,1720,1675,1599,1525,149
9,1438,1321,1253,1161,1087/cm. [α]D=−16.6゜(CHCl3,c=1.03,24.0℃)mp.100−
101℃ No.1a−93 CDCl3+CD3OD 300MHz 0.96−2.00(14H,m),2.18−2.35(3H,m),2.90(1H,
m),5.15−5.30(2H,m),7.18(1H,m),7.33−7.42(2
H,m),7.65−7.74(2H,m),7.90−8.08(4H,m). IR(KBr):3347,3194,3011,2955,2875,1706,1650,1602,
1544,1499,1443,1325,1265,1165,1091/cm. [α]D=−19.4゜(CH3OH,c=1.00,24.0℃)mp.158−
159℃ No.1a−94 CD3OD 300MHz 1.05−2.00(14H,m),2.14(1H,m),2.23(2H,t,J=7.2
Hz),2.98(1H,m),3.80(3H,s),5.13−5.27(2H,m),
6.88−6.98(2H,m),7.54−7.64(2H,m),7.94−8.12
(4H,m). IR(KBr):3370,3006,2953,1708,1649,1604,1541,1512,
1460,1441,1414,1328,1302,1248,1162,1107,1090,1032/
cm. [α]D=−19.1゜(CH3OH,c=1.01,24℃). No.1a−95 CD3OD 300MHz 1.04−2.02(14H,m),2.14(1H,m),2.23(2H,t,J=7.2
Hz),2.93−3.02(7H,m),5.13−5.27(2H,m),6.82−
6.92(2H,m),7.51−7.59(2H,m),7.95−8.02(2H,
m),8.04−8.11(2H,m). IR(KBr):3370,3006,2953,1708,1649,1604,1541,1512,
1460,1441,1414,1328,1302,1248,1162,1107,1090,1032/
cm. [α]D==−17.6゜(CH3OH,c=1.01,24℃). No.1a−96 CD3OD 300MHz 1.05−2.02(14H,m),2.14(1H,m),2.23(2H,t,J=7.2
Hz),2.98(1H,m),5.13−5.27(2H,m),6.75−6.84(2
H,m),7.43−7.52(2H,m),7.94−8.12(4H,m). IR(KBr):3339,3197,2953,2875,1707,1644,1606,1541,
1514,1446,1325,1293,1259,1240,1225,1161,1091/cm. [α]D=−18.7゜(CH3OH,c=1.00,24℃).mp.193−1
96℃ No.1a−97 d6−DMSO 300MHz 1.05−2.08(15H,m),2.15(2H,t,J=7.5Hz),2.89(1
H,m),5.18−5.28(2H,m),6.78−7.12(3H,m),7.73
(1H,d.d,J=1.4and7.8Hz),7.91−7.95(3H,m),8.14
(2H,d,J=8.4Hz),9.71(1H,s). IR(KBr):3407,3191,2953,1711,1646,1614,1603,1537,
1457,1326,1162,1151/cm [α]D=−20.7゜(CH3OH,C=1.01,21℃). No.1a−98 CDCl3 300MHz 0.93−2.00(14H,m),2.21(1H,m),2.31(2H,t,J=7.2
Hz),2.93(1H,m),3.84(3H,s),3.85(6H,s),5.15−
5.30(2H,m),5.45(1H,d,J=6.3Hz),7.04(2H,s),7.
78−7.86(2H,m),7.90−7.98(2H,m),8.58(1H,s). IR(CHCl3):3264,3008,2954,2874,1707,1670,1607,153
7,1506,1451,1421,1308,1158,1129,1088/cm. [α]D=−7.2゜(CHCl3,C=1.01,23.5℃).mp.147−
149℃ No.1a−99 CD3OD 300MHz 1.04−1.98(14H,m),2.21(1H,m),2.10(2H,t,J=7.2
Hz),2.95(1H,m),3.76(3H,s),3.86(6H,s),5.07−
5.24(2H,m),7.19(2H,s),7.99(2H,d,J=8.7Hz),8.
13(1H,d,J=8.7Hz). IR(KBr):3354,3002,2950,2874,1656,1607,1570,1508,
1452,1413,1314,1233,1185,1157,1127,1092/cm. [α]D=−20.3゜(CH3OH,C=1.00,23.5℃). No.1a−100 CDCl3 300MHz 1.14−1.97(14H,m),2.19(1H,m),2.28(2H,t,J=7.4
Hz),3.04(1H,m),3.69(3H,s),5.03(1H,d,J=6.9H
z),5.15−5.29(2H,m),7.65(2H,d,J=8.4Hz),7.87
(1H,s),7.98(2H,d,J=8.4Hz). IR(CHCl3):3386,3271,3025,3015,2955,2877,1755,171
2,1608,1331,1162/cm. [α]D=−29.4゜(CH3OH,c=1.01,25℃)。
m),5.15−5.30(2H,m),7.82−7.92(4H,m),8.09−8.
16(2H,m),8.30−8.37(2H,m). IR(KBr):3284,3112,3006,2952,2874,1707,1593,1528,
1498,1399,1348,1320,1259,1153,1093/cm. [α]D=−26.3゜(CH3OH,c=1.01,22℃). No.1a−92 CDCl3 300MHz 0.93−1.95(14H,m),2.22−2.31(3H,m),2.98(1H,
m),3.68(3H,s),5.07(1H,d,J=6.9Hz),5.10−5.24
(2H,m),7.18(1H,m),7.35−7.43(2H,m),7.70(2H,
d,J=7.8Hz),7.88−8.05(4H,m),8.50(1H,brs). IR(CHCl3):3382,3008,2952,1720,1675,1599,1525,149
9,1438,1321,1253,1161,1087/cm. [α]D=−16.6゜(CHCl3,c=1.03,24.0℃)mp.100−
101℃ No.1a−93 CDCl3+CD3OD 300MHz 0.96−2.00(14H,m),2.18−2.35(3H,m),2.90(1H,
m),5.15−5.30(2H,m),7.18(1H,m),7.33−7.42(2
H,m),7.65−7.74(2H,m),7.90−8.08(4H,m). IR(KBr):3347,3194,3011,2955,2875,1706,1650,1602,
1544,1499,1443,1325,1265,1165,1091/cm. [α]D=−19.4゜(CH3OH,c=1.00,24.0℃)mp.158−
159℃ No.1a−94 CD3OD 300MHz 1.05−2.00(14H,m),2.14(1H,m),2.23(2H,t,J=7.2
Hz),2.98(1H,m),3.80(3H,s),5.13−5.27(2H,m),
6.88−6.98(2H,m),7.54−7.64(2H,m),7.94−8.12
(4H,m). IR(KBr):3370,3006,2953,1708,1649,1604,1541,1512,
1460,1441,1414,1328,1302,1248,1162,1107,1090,1032/
cm. [α]D=−19.1゜(CH3OH,c=1.01,24℃). No.1a−95 CD3OD 300MHz 1.04−2.02(14H,m),2.14(1H,m),2.23(2H,t,J=7.2
Hz),2.93−3.02(7H,m),5.13−5.27(2H,m),6.82−
6.92(2H,m),7.51−7.59(2H,m),7.95−8.02(2H,
m),8.04−8.11(2H,m). IR(KBr):3370,3006,2953,1708,1649,1604,1541,1512,
1460,1441,1414,1328,1302,1248,1162,1107,1090,1032/
cm. [α]D==−17.6゜(CH3OH,c=1.01,24℃). No.1a−96 CD3OD 300MHz 1.05−2.02(14H,m),2.14(1H,m),2.23(2H,t,J=7.2
Hz),2.98(1H,m),5.13−5.27(2H,m),6.75−6.84(2
H,m),7.43−7.52(2H,m),7.94−8.12(4H,m). IR(KBr):3339,3197,2953,2875,1707,1644,1606,1541,
1514,1446,1325,1293,1259,1240,1225,1161,1091/cm. [α]D=−18.7゜(CH3OH,c=1.00,24℃).mp.193−1
96℃ No.1a−97 d6−DMSO 300MHz 1.05−2.08(15H,m),2.15(2H,t,J=7.5Hz),2.89(1
H,m),5.18−5.28(2H,m),6.78−7.12(3H,m),7.73
(1H,d.d,J=1.4and7.8Hz),7.91−7.95(3H,m),8.14
(2H,d,J=8.4Hz),9.71(1H,s). IR(KBr):3407,3191,2953,1711,1646,1614,1603,1537,
1457,1326,1162,1151/cm [α]D=−20.7゜(CH3OH,C=1.01,21℃). No.1a−98 CDCl3 300MHz 0.93−2.00(14H,m),2.21(1H,m),2.31(2H,t,J=7.2
Hz),2.93(1H,m),3.84(3H,s),3.85(6H,s),5.15−
5.30(2H,m),5.45(1H,d,J=6.3Hz),7.04(2H,s),7.
78−7.86(2H,m),7.90−7.98(2H,m),8.58(1H,s). IR(CHCl3):3264,3008,2954,2874,1707,1670,1607,153
7,1506,1451,1421,1308,1158,1129,1088/cm. [α]D=−7.2゜(CHCl3,C=1.01,23.5℃).mp.147−
149℃ No.1a−99 CD3OD 300MHz 1.04−1.98(14H,m),2.21(1H,m),2.10(2H,t,J=7.2
Hz),2.95(1H,m),3.76(3H,s),3.86(6H,s),5.07−
5.24(2H,m),7.19(2H,s),7.99(2H,d,J=8.7Hz),8.
13(1H,d,J=8.7Hz). IR(KBr):3354,3002,2950,2874,1656,1607,1570,1508,
1452,1413,1314,1233,1185,1157,1127,1092/cm. [α]D=−20.3゜(CH3OH,C=1.00,23.5℃). No.1a−100 CDCl3 300MHz 1.14−1.97(14H,m),2.19(1H,m),2.28(2H,t,J=7.4
Hz),3.04(1H,m),3.69(3H,s),5.03(1H,d,J=6.9H
z),5.15−5.29(2H,m),7.65(2H,d,J=8.4Hz),7.87
(1H,s),7.98(2H,d,J=8.4Hz). IR(CHCl3):3386,3271,3025,3015,2955,2877,1755,171
2,1608,1331,1162/cm. [α]D=−29.4゜(CH3OH,c=1.01,25℃)。
No.1a−101 d6−DMSO 1.00−2.20(17H,m),2.84(1H,m),5.00−5.20(2H,
m),7.78(2H,d,J=8.2Hz),7.84(1H,s),7.89−7.95
(3H,m). IR(KBr):3269,3065,3008,2952,2874,2763,1746,1707,
1607,1322,1157/cm. [α]D=−26.2゜(CH3OH,c=1.01,25℃)。
m),7.78(2H,d,J=8.2Hz),7.84(1H,s),7.89−7.95
(3H,m). IR(KBr):3269,3065,3008,2952,2874,2763,1746,1707,
1607,1322,1157/cm. [α]D=−26.2゜(CH3OH,c=1.01,25℃)。
No.1a−102 CD3OD 1.00−2.25(17H,m),2.92(1H,s),3.64(3H,s),5.07
−5.21(2H,m),7.53(1H,s),7.77(2H,d,J=8.6Hz),
7.90(2H,d,J=8.6). IR(KBr):3430,3277,3006,2952,2873,1720,1687,1620,
1571,1438,1312,1156/cm. [α]D=−27.3゜(CH3OH,c=0.51,26℃)。mp.230−
232℃ No.1a−103 CDCl3 300MHz 0.94−1.96(14H,m),2.19(1H,m),2.28(2H,t,J=7.2
Hz),3.04(1H,m),3.69(3H,s),5.11(1H,d,J=6.6H
z),5.15−5.28(2H,m),7.60(2H,d,J=8.4Hz),7.67
(1H,s),7.98(2H,d,J=8.4Hz). IR(CHCl3):3381,3021,2955,2876,1735,1605,1437,141
1,1325,1231,1177/cm. [α]D=+8.6゜(CHCl3,c=1.00,23℃)。
−5.21(2H,m),7.53(1H,s),7.77(2H,d,J=8.6Hz),
7.90(2H,d,J=8.6). IR(KBr):3430,3277,3006,2952,2873,1720,1687,1620,
1571,1438,1312,1156/cm. [α]D=−27.3゜(CH3OH,c=0.51,26℃)。mp.230−
232℃ No.1a−103 CDCl3 300MHz 0.94−1.96(14H,m),2.19(1H,m),2.28(2H,t,J=7.2
Hz),3.04(1H,m),3.69(3H,s),5.11(1H,d,J=6.6H
z),5.15−5.28(2H,m),7.60(2H,d,J=8.4Hz),7.67
(1H,s),7.98(2H,d,J=8.4Hz). IR(CHCl3):3381,3021,2955,2876,1735,1605,1437,141
1,1325,1231,1177/cm. [α]D=+8.6゜(CHCl3,c=1.00,23℃)。
No.1a−104 CDCl3 300MHz 0.94−1.96(14H,m),2.21(1H,m),2.31(2H,t,J=6.8
Hz),2.99(1H,m),5.18−5.28(2H,m),5.45(1H,d,J
=6.6Hz),7.61(2H,d,J=8.7Hz),7.67(1H,s),7.99
(2H,d,J=8.7Hz). IR(CHCl3):3382,3222,3028,3019,2957,2876,1736,170
9,1604,1412,1322,1301,1286,1179,1162/cm. [α]D=+10.4゜(CHCl3,c=1.00,23℃)。
Hz),2.99(1H,m),5.18−5.28(2H,m),5.45(1H,d,J
=6.6Hz),7.61(2H,d,J=8.7Hz),7.67(1H,s),7.99
(2H,d,J=8.7Hz). IR(CHCl3):3382,3222,3028,3019,2957,2876,1736,170
9,1604,1412,1322,1301,1286,1179,1162/cm. [α]D=+10.4゜(CHCl3,c=1.00,23℃)。
No.1a−105 CDCl3 300MHz 0.92−1.98(14H,m),2.17(1H,m),2.26(2H,d,J=7.5
Hz),3.01(1H,m),3.69(3H,s),4.01(3H,s),4.84
(1H,d,J=6.3Hz),5.14−5.30(2H,m),7.71(2H,d,J
=8.7Hz),7.87(2H,d,J=8.7Hz),8.09(1H,s). IR(CHCl3):3385,3284,3025,3015,2954,2877,2821,173
0,1598,1459,1438,1403,1341,1160,1052/cm. [α]D=+3.6゜(CHCl3,c=1.00,26℃)。
Hz),3.01(1H,m),3.69(3H,s),4.01(3H,s),4.84
(1H,d,J=6.3Hz),5.14−5.30(2H,m),7.71(2H,d,J
=8.7Hz),7.87(2H,d,J=8.7Hz),8.09(1H,s). IR(CHCl3):3385,3284,3025,3015,2954,2877,2821,173
0,1598,1459,1438,1403,1341,1160,1052/cm. [α]D=+3.6゜(CHCl3,c=1.00,26℃)。
No.1a−106 CDCl3 300MHz 0.92−2.08(14H,m),2.14(1H,m),2.34(2H,d,J=7.2
Hz),3.02(1H,m),4.01(3H,s),5.19(1H,d,J=6.9H
z),5.23−5.32(2H,m),7.71(2H,d,J=8.4Hz),7.88
(2H,d,J=8.4Hz),8.09(1H,s). IR(CHCl3):3510,3384,3268,3028,3021,3014,2957,287
7,2821,2667,2821,2666,1707,1598,1459,1404,1341,132
4,1160,1052/cm. [α]D=+11.8゜(CHCl3,c=1.01,25℃).mp.95−96
℃ No.1a−107 CDCl3 300MHz 0.92−1.97(14H,m),1.34(3H,t,J=7.2Hz),2.18(1
H,m),2.28(2H,d,J=7.4Hz),3.01(1H,m),3.68(3H,
s),4.26(2H,q,J=7.2Hz),4.86(1H,d,J=6.6Hz),5.
15−5.29(2H,m),7.71(2H,d,J=8.7Hz),7.87(2H,d,
J=8.7Hz),8.09(1H,s). IR(CHCl3):3385,3282,3025,3026,3015,2954,2877,172
9,1599,1480,1458,1438,1403,1338,1161/cm. [α]D=+4.4゜(CHCl3,c=1.00,25℃)。
Hz),3.02(1H,m),4.01(3H,s),5.19(1H,d,J=6.9H
z),5.23−5.32(2H,m),7.71(2H,d,J=8.4Hz),7.88
(2H,d,J=8.4Hz),8.09(1H,s). IR(CHCl3):3510,3384,3268,3028,3021,3014,2957,287
7,2821,2667,2821,2666,1707,1598,1459,1404,1341,132
4,1160,1052/cm. [α]D=+11.8゜(CHCl3,c=1.01,25℃).mp.95−96
℃ No.1a−107 CDCl3 300MHz 0.92−1.97(14H,m),1.34(3H,t,J=7.2Hz),2.18(1
H,m),2.28(2H,d,J=7.4Hz),3.01(1H,m),3.68(3H,
s),4.26(2H,q,J=7.2Hz),4.86(1H,d,J=6.6Hz),5.
15−5.29(2H,m),7.71(2H,d,J=8.7Hz),7.87(2H,d,
J=8.7Hz),8.09(1H,s). IR(CHCl3):3385,3282,3025,3026,3015,2954,2877,172
9,1599,1480,1458,1438,1403,1338,1161/cm. [α]D=+4.4゜(CHCl3,c=1.00,25℃)。
No.1a−108 CDCl3 300MHz 0.90−2.04(14H,m),1.34(3H,t,J=7.2Hz),2.14(1
H,m),2.34(2H,d,J=7.1Hz),3.01(1H,m),4.27(2H,
q,J=7.2Hz),5.20(1H,d,J=6.6Hz),5.21−5.35(2H,
m),7.71(2H,d,J=8.4Hz),7.88(2H,d,J=8.4Hz),8.
10(1H,s). IR(CHCl3):3514,3384,3270,3025,3015,3015,2957,287
7,1708,1599,1458,1403,1324,1324,1160,1050/cm. [α]D=+12.7゜(CHCl3,c=1.00,25℃)。
H,m),2.34(2H,d,J=7.1Hz),3.01(1H,m),4.27(2H,
q,J=7.2Hz),5.20(1H,d,J=6.6Hz),5.21−5.35(2H,
m),7.71(2H,d,J=8.4Hz),7.88(2H,d,J=8.4Hz),8.
10(1H,s). IR(CHCl3):3514,3384,3270,3025,3015,3015,2957,287
7,1708,1599,1458,1403,1324,1324,1160,1050/cm. [α]D=+12.7゜(CHCl3,c=1.00,25℃)。
No.1a−109 [α]D=+8.5゜(CHCl3,c=1.00,25℃)。mp.109.0
−111.0℃ No.1a−110 CDCl3:CD3OD(95:5) 0.92−2.06(14H,m),2.20(1H,m),2.30(2H,d,J=7.2
Hz),2.99(1H,m),5.22−5.33(2H,m),7.54−7.66(3
H,m),8.07(2H,d,J=9.0Hz),8.12−8.20(2H,m),8.2
9(2H,d,J=9.0Hz). IR(Nujol):3270,2956,2924,2854,1716,1548,1485,131
9,1167/cm. [α]D=+17.0゜(CHCl3,c=1.00,25℃).mp.166.5
−168℃ No.1a−111 [α]D=+2.6゜(CHCl3,c=1.00,24℃)。mp.120.0
−121.0℃ No.1a−112 CDCl3 300MHz 0.96−2.04(14H,m),2.19(1H,m),2.33(2H,d,J=7.1
Hz),3.07(1H,m),5.28−5.31(2H,m),5.33(1H,d,J
=6.6Hz),7.54−7.63(3H,m),8.05(2H,d,J=8.4H
z),8.18−8.23(2H,m),8.41(2H,d,J=8.4Hz). IR(CHCl3):3384,3269,3025,3015,2957,2877,1708,159
8,1496,1457,1417,1326,1164/cm. [α]D=+12.2゜(CHCl3,c=1.00,24℃).mp.163−1
64℃ No.1a−113 [α]D=+22.1゜(CHCl3,c=1.05,25℃).mp.90−92
℃ No.1a−114 [α]D=+2.2゜(CHCl3,c=1.02,25℃)。
−111.0℃ No.1a−110 CDCl3:CD3OD(95:5) 0.92−2.06(14H,m),2.20(1H,m),2.30(2H,d,J=7.2
Hz),2.99(1H,m),5.22−5.33(2H,m),7.54−7.66(3
H,m),8.07(2H,d,J=9.0Hz),8.12−8.20(2H,m),8.2
9(2H,d,J=9.0Hz). IR(Nujol):3270,2956,2924,2854,1716,1548,1485,131
9,1167/cm. [α]D=+17.0゜(CHCl3,c=1.00,25℃).mp.166.5
−168℃ No.1a−111 [α]D=+2.6゜(CHCl3,c=1.00,24℃)。mp.120.0
−121.0℃ No.1a−112 CDCl3 300MHz 0.96−2.04(14H,m),2.19(1H,m),2.33(2H,d,J=7.1
Hz),3.07(1H,m),5.28−5.31(2H,m),5.33(1H,d,J
=6.6Hz),7.54−7.63(3H,m),8.05(2H,d,J=8.4H
z),8.18−8.23(2H,m),8.41(2H,d,J=8.4Hz). IR(CHCl3):3384,3269,3025,3015,2957,2877,1708,159
8,1496,1457,1417,1326,1164/cm. [α]D=+12.2゜(CHCl3,c=1.00,24℃).mp.163−1
64℃ No.1a−113 [α]D=+22.1゜(CHCl3,c=1.05,25℃).mp.90−92
℃ No.1a−114 [α]D=+2.2゜(CHCl3,c=1.02,25℃)。
No.1a−115 CDCl3 300MHz 0.90−1.98(14H,m),2.15−2.22(1H,m),2.27(2H,t,
J=7.2Hz),2.95−3.04(1H,m),3.68(3H,s),4.04(2
H,s),4.85(1H,d,J=6.6Hz),5.10−5.27(2H,m),7.1
2−7.34(7H,m),7.76−7.82(2H,m). IR(CHCl3):3384,3026,2952,1727,1595,1493,1436,131
8,1155,1091,890/cm. [α]D==0゜ [α]436=+4.9±0.4゜(CHCl3,c=1.05,23℃) No.1a−116 CDCl3 300MHz 0.90−2.10(14H,m),2.10−2.18(1H,m),2.32(2H,t,
J=7.2Hz),2.96−3.04(1H,m),4.04(2H,s),5.14(1
H,d,J=6.6Hz),5.16−5.28(2H,m),7.12−7.34(7H,
m),7.76−7.82(2H,m). IR(CHCl3):3260,3020,2950,1709,1407,1318,1154,109
1,892/cm. [α]D==+9.1±0.5゜(CHCl3,c=1.04,23℃) No.1a−117 CD3OD 300MHz 0.96−2.18(17H,m),2.89−2.92(1H,m),4.05(2H,
s),4.95−5.22(2H,m),7.15−7.42(7H,m),7.75−7.
81(2H,m). IR(KBr):3429,3279,2951,2872,1563,1494,1453,1408,
1313,1155,1093,1057/cm. [α]D==−16.3±0.5゜(CH3OH,c=1.06,25℃) No.1a−118 CDCl3 300MHz 0.98−1.70(15H,m),1.80−2.00(5H,m),2.20−2.40
(3H,m),2.98(1H,m),4.06(2H,s),4.72(1H,d,J=
6.3Hz),5.00−5.23(3H,m),7.16(2H,d,J=8.4Hz),
7.26−7.33(5H,m),7.79(2H,d,J=8.1Hz). IR(CHCl3):3376,3020,2948,2868,1716,1596,1492,145
3,1407,1318,1155,1105/cm. [α]D=+2.4゜(CHCl3,c=1.08,24℃). No.1a−119 CDCl3 300MHz 0.90−2.02(14H,m),2.20(1H,m),2.29(2H,t,J=7.2
Hz),3.00(1H,m),3.68(3H,s),4.86(1H,d,J=6.9H
z),5.13−5.34(2H,m),7.00−7.09(4H,m),7.22(1
H,m),7.37−7.45(2H,m),7.79−7.86(2H,m). IR(CHCl3):3376,3018,2946,2868,1727,1582,1486,132
1,1243,1151,1093/cm. [α]D=+4.5゜(CHCl3,c=1.05,23.5℃)。
J=7.2Hz),2.95−3.04(1H,m),3.68(3H,s),4.04(2
H,s),4.85(1H,d,J=6.6Hz),5.10−5.27(2H,m),7.1
2−7.34(7H,m),7.76−7.82(2H,m). IR(CHCl3):3384,3026,2952,1727,1595,1493,1436,131
8,1155,1091,890/cm. [α]D==0゜ [α]436=+4.9±0.4゜(CHCl3,c=1.05,23℃) No.1a−116 CDCl3 300MHz 0.90−2.10(14H,m),2.10−2.18(1H,m),2.32(2H,t,
J=7.2Hz),2.96−3.04(1H,m),4.04(2H,s),5.14(1
H,d,J=6.6Hz),5.16−5.28(2H,m),7.12−7.34(7H,
m),7.76−7.82(2H,m). IR(CHCl3):3260,3020,2950,1709,1407,1318,1154,109
1,892/cm. [α]D==+9.1±0.5゜(CHCl3,c=1.04,23℃) No.1a−117 CD3OD 300MHz 0.96−2.18(17H,m),2.89−2.92(1H,m),4.05(2H,
s),4.95−5.22(2H,m),7.15−7.42(7H,m),7.75−7.
81(2H,m). IR(KBr):3429,3279,2951,2872,1563,1494,1453,1408,
1313,1155,1093,1057/cm. [α]D==−16.3±0.5゜(CH3OH,c=1.06,25℃) No.1a−118 CDCl3 300MHz 0.98−1.70(15H,m),1.80−2.00(5H,m),2.20−2.40
(3H,m),2.98(1H,m),4.06(2H,s),4.72(1H,d,J=
6.3Hz),5.00−5.23(3H,m),7.16(2H,d,J=8.4Hz),
7.26−7.33(5H,m),7.79(2H,d,J=8.1Hz). IR(CHCl3):3376,3020,2948,2868,1716,1596,1492,145
3,1407,1318,1155,1105/cm. [α]D=+2.4゜(CHCl3,c=1.08,24℃). No.1a−119 CDCl3 300MHz 0.90−2.02(14H,m),2.20(1H,m),2.29(2H,t,J=7.2
Hz),3.00(1H,m),3.68(3H,s),4.86(1H,d,J=6.9H
z),5.13−5.34(2H,m),7.00−7.09(4H,m),7.22(1
H,m),7.37−7.45(2H,m),7.79−7.86(2H,m). IR(CHCl3):3376,3018,2946,2868,1727,1582,1486,132
1,1243,1151,1093/cm. [α]D=+4.5゜(CHCl3,c=1.05,23.5℃)。
No.1a−120 CD3OD 300MHz 1.00−2.00(14H,m),2.13(2H,t,J=7.5Hz),2.16(1
H,m),2.91(1H,m),5.05−5.33(2H,m),7.04−7.11
(4H,m),7.18−7.25(1H,m),7.38−7.48(2H,m),7.8
0−7.87(2H,m). IR(KBr):3430,3278,3006,2952,2873,1583,1487,1410,
1322,1298,1245,1152,1095/cm. [α]D=−8.8゜(CH3OH,c=1.05,25.0℃)。
H,m),2.91(1H,m),5.05−5.33(2H,m),7.04−7.11
(4H,m),7.18−7.25(1H,m),7.38−7.48(2H,m),7.8
0−7.87(2H,m). IR(KBr):3430,3278,3006,2952,2873,1583,1487,1410,
1322,1298,1245,1152,1095/cm. [α]D=−8.8゜(CH3OH,c=1.05,25.0℃)。
No.1a−121 CDCl3 300MHz 0.90−2.10(14H,m),2.15(1H,m),2.35(2H,t,J=7.2
Hz),3.01(1H,m),5.20(1H,d,J=6.9Hz),5.22−5.35
(2H,m),7.00−7.09(4H,m),7.18−7.25(1H,m),7.3
7−7.45(2H,m),7.79−7.86(2H,m). IR(CHCl3):3260,3020,2948,2868,1708,1582,1486,140
9,1321,1296,1243,1151,1093/cm. [α]D=+13.1゜(CHCl3,c=1.04,24.0℃)。
Hz),3.01(1H,m),5.20(1H,d,J=6.9Hz),5.22−5.35
(2H,m),7.00−7.09(4H,m),7.18−7.25(1H,m),7.3
7−7.45(2H,m),7.79−7.86(2H,m). IR(CHCl3):3260,3020,2948,2868,1708,1582,1486,140
9,1321,1296,1243,1151,1093/cm. [α]D=+13.1゜(CHCl3,c=1.04,24.0℃)。
No.1a−122 CDCl3 300MHz 0.90−2.00(14H,m),2.23(1H,m),2.28(2H,t,J=7.5
Hz),2.96(1H,m),3.67(3H,s),4.69(1H,d,J=6.6H
z),5.15−5.32(2H,m),6.22(1H,s),6.98−7.40(5
H,m),7.30−7.38(2H,m),7.68−7.74(2H,m). IR(CHCl3):3416,3370,3018,2946,2868,1725,1587,150
8,1437,1400,1320,1149,1094/cm. [α]D=+6.2゜(CHCl3,c=1.04,25.0℃)。
Hz),2.96(1H,m),3.67(3H,s),4.69(1H,d,J=6.6H
z),5.15−5.32(2H,m),6.22(1H,s),6.98−7.40(5
H,m),7.30−7.38(2H,m),7.68−7.74(2H,m). IR(CHCl3):3416,3370,3018,2946,2868,1725,1587,150
8,1437,1400,1320,1149,1094/cm. [α]D=+6.2゜(CHCl3,c=1.04,25.0℃)。
No.1a−123 CDCl3 300MHz 0.90−2.04(14H,m),2.18(1H,m),2.33(2H,t,J=7.2
Hz),2.96(1H,m),5.04−5.35(3H,m),6.98−7.12(3
H,m),7.12−7.20(2H,m),7.28−7.38(2H,m),7.66−
7.74(2H,m). IR(CHCl3):3424,3270,3028,2952,2872,1708,1587,150
8,1445,1399,1320,1148,1092/cm. [α]D=+20.9゜(CHCl3,c=1.06,23.0℃)。
Hz),2.96(1H,m),5.04−5.35(3H,m),6.98−7.12(3
H,m),7.12−7.20(2H,m),7.28−7.38(2H,m),7.66−
7.74(2H,m). IR(CHCl3):3424,3270,3028,2952,2872,1708,1587,150
8,1445,1399,1320,1148,1092/cm. [α]D=+20.9゜(CHCl3,c=1.06,23.0℃)。
No.1a−124 CDCl3 300MHz 0.90−2.00(14H,m),2.18(1H,m),2.28(2H,t,J=7.2
Hz),3.00(1H,m),3.14(1H,m),3.68(3H,s),4.56
(2H,s),4.84(1H,d,J=6.3Hz),5.10−5.29(2H,m),
7.16−7.26(4H,m),7.26−7.34(2H,m),7.78−7.84
(2H,m). IR(CHCl3):3384,3028,2952,2874,1727,1598,1501,143
5,1410,1370,1329,1172,1148,1091/cm. [α]D=+2.7゜(CHCl3,c=1.09,23.0℃)。
Hz),3.00(1H,m),3.14(1H,m),3.68(3H,s),4.56
(2H,s),4.84(1H,d,J=6.3Hz),5.10−5.29(2H,m),
7.16−7.26(4H,m),7.26−7.34(2H,m),7.78−7.84
(2H,m). IR(CHCl3):3384,3028,2952,2874,1727,1598,1501,143
5,1410,1370,1329,1172,1148,1091/cm. [α]D=+2.7゜(CHCl3,c=1.09,23.0℃)。
No.1a−125 CDCl3 300MHz 0.90−2.00(14H,m),2.18(1H,m),2.28(2H,t,J=7.2
Hz),2.29(3H,s),3.00(1H,m),3.68(3H,s),4.04
(2H,s),4.80(1H,d,J=6.6Hz),5.11−5.29(2H,m),
6.99−7.06(2H,m),7.12−7.19(2H,m),7.31(2H,d,J
=8.1Hz),7.79(2H,d,J=8.1Hz). IR(CHCl3):3382,3280,3024,2950,2874,1730,1596,150
4,1435,1407,1367,1318,1196,1155,1091/cm. [α]D=+2.9゜(CHCl3,c=1.06,23.0℃)。
Hz),2.29(3H,s),3.00(1H,m),3.68(3H,s),4.04
(2H,s),4.80(1H,d,J=6.6Hz),5.11−5.29(2H,m),
6.99−7.06(2H,m),7.12−7.19(2H,m),7.31(2H,d,J
=8.1Hz),7.79(2H,d,J=8.1Hz). IR(CHCl3):3382,3280,3024,2950,2874,1730,1596,150
4,1435,1407,1367,1318,1196,1155,1091/cm. [α]D=+2.9゜(CHCl3,c=1.06,23.0℃)。
No.1a−126 CDCl3 300MHz 0.90−2.02(14H,m),2.14(1H,m)2.29(3H,s),2.32
(2H,t,J=7.2Hz),3.01(1H,m),4.03(2H,s),5.10
(1H,d,J=6.6Hz),5.15−5.30(2H,m),6.98−7.06(2
H,m),7.11−7.18(2H,m),7.30(2H,d,J=8.1Hz),7.7
9(2H,d,J=8.1Hz). IR(CHCl3):3374,3260,3020,2948,2868,1749,1708,159
6,1504,1407,1369,1317,1195,1155,1091/cm. [α]D=+10.0゜(CHCl3,c=1.09,23.0℃)。
(2H,t,J=7.2Hz),3.01(1H,m),4.03(2H,s),5.10
(1H,d,J=6.6Hz),5.15−5.30(2H,m),6.98−7.06(2
H,m),7.11−7.18(2H,m),7.30(2H,d,J=8.1Hz),7.7
9(2H,d,J=8.1Hz). IR(CHCl3):3374,3260,3020,2948,2868,1749,1708,159
6,1504,1407,1369,1317,1195,1155,1091/cm. [α]D=+10.0゜(CHCl3,c=1.09,23.0℃)。
No.1a−127 CDCl3 300MHz 0.87−1.95(14H,m),2.18−2.32(3H,m),2.95(1H,
m),3.69(3H,s),3.96(2H,s),4.79(1H,d,J=6.6H
z),4.97−5.17(2H,m),5.54(1H,s),6.75−6.82(2
H,m),6.97−7.05(2H,m),7.25−7.33(2H,m),7.75−
7.81(2H,m). IR(CHCl3):3382,3026,2950,2874,1722,1595,1511,143
6,1407,1317,1257,1154,1090/cm. [α]D=−2.1゜(CHCl3,c=1.00,21.5℃)。
m),3.69(3H,s),3.96(2H,s),4.79(1H,d,J=6.6H
z),4.97−5.17(2H,m),5.54(1H,s),6.75−6.82(2
H,m),6.97−7.05(2H,m),7.25−7.33(2H,m),7.75−
7.81(2H,m). IR(CHCl3):3382,3026,2950,2874,1722,1595,1511,143
6,1407,1317,1257,1154,1090/cm. [α]D=−2.1゜(CHCl3,c=1.00,21.5℃)。
No.1a−128 CDCl3 300MHz 0.85−2.02(14H,m),2.18(1H,m),2.31(2H,t,J=7.2
Hz),2.96(1H,m),3.95(2H,s),5.05−5.27(4H,m),
6.73−6.82(2H,m),6.96−7.04(2H,m),7.25−7.32
(2H,m),7.74−7.81(2H,m). IR(CHCl3):3262,3020,2948,2868,1708,1596,1511,140
7,1315,1242,1154,1091/cm. [α]D=+4.8゜(CHCl3,c=1.04,22℃). No.1a−129 CDCl3 300MHz 0.89−1.98(14H,m),2.18(1H,m),2.27(2H,t,J=7.2
Hz),2.99(1H,m),3.68(3H,s),3.79(3H,s),3.98
(2H,s),4.81(1H,d,J=6.6Hz),5.10−5.27(2H,m),
6.81−6.87(2H,m),7.03−7.10(2H,m),7.25−7.32
(2H,m),7.75−7.82(2H,m). IR(CHCl3):3382,3276,3006,2950,2874,1726,1609,150
9,1457,1436,1407,1315,1244,1154,1091,1033/cm. [α]D=+19.3゜(CHCl3,C=1.05,23℃). No.1a−130 CDCl3 300MHz 0.90−2.00(14H,m),2.20(1H,m),2.30(2H,t,J=7.2
Hz),2.98(1H,m),3.69(3H,s),4.81(1H,d,J=6.6H
z),5.12−5.32(2H,m),5.46(1H,brs),6.84−7.01
(6H,m),7.76−7.83(2H,m) IR(CHCl3):3380,3284,3024,2952,2874,1724,1588,150
4,1488,1436,1321,1296,1149,1091/cm. [α]D=+28.9゜(CHCl3,c=1.01,23℃). No.1a−131 CDCl3 300MHz 0.92−2.10(14H,m),2.18(1H,m),2.34(2H,t,J=6.9
Hz),2.96(1H,m),5.18−5.35(3H,m),6.84−7.01(6
H,m),7.75−7.83(2H,m). IR(CHCl3):3270,3028,2952,2874,1708,1589,1505,148
9,1456,1322,1297,1238,1148,1091/cm. [α]D=+7.7゜(CHCl3,C=1.09,24℃). No.1a−132 CDCl3 300MHz 0.91−2.02(14H,m),2.19(1H,m),2.29(2H,t,J=7.2
Hz),2.99(1H,m),3.68(3H,s),3.83(3H,s),4.82
(1H,d,J=6.6Hz),5.14−5.33(2H,m),6.90−7.04(6
H,m),7.76−7.83(2H,m). IR(CHCl3):3384,3006,2952,2874,1727,1589,1502,148
8,1459,1438,1321,1295,1231,1150,1092,1033/cm. [α]D=+3.1゜(CHCl3,C=1.01,23℃). No.1a−133 TLC Rf=0.21(酢酸エチル:n−ヘキサン=1:1(0.3%酢
酸)) No.1a−134 CDCl3 300MHz 0.97−2.10(14H,m),2.20(1H,m),2.36(2H,t,J=6.9
Hz),3.04(1H,m),5.22−5.33(2H,m),5.41(1H,d,J
=6.6Hz),7.02(1H,d,J=9.0Hz),7.09−7.13(2H,
m),7.26−7.32(1H,m),7.43−7.49(2H,m),7.93(1
H,d.d,J=2.4and9.0Hz),8.46(1H,d,J=2.4Hz). IR(CHCl3):3384,3270,3020,2958,1709,1610,1587,153
7,1479,1352,1271,1252,1167/cm. [α]D=+20.9゜(CHCl3,C=0.51,22℃). No.1a−135 CDCl3 300MHz 0.96−2.02(14H,m),2.21(1H,m),2.29(2H,t,J=7.2
Hz),3.07(1H,m),3.68(3H,s),5.04(1H,d,J=6.9H
z),5.16−5.33(2H,m),7.48−7.55(2H,m),7.64(1
H,m),7.76−7.82(2H,m),7.88−7.94(2H,m),7.98−
8.04(2H,m). IR(CHCl3):3384,3282,3026,2952,2874,1727,1663,159
6,1446,1396,1316,1274,1163,1090/cm. [α]D=+3.1゜(CHCl3,c=1.03,22.0℃)。
Hz),2.96(1H,m),3.95(2H,s),5.05−5.27(4H,m),
6.73−6.82(2H,m),6.96−7.04(2H,m),7.25−7.32
(2H,m),7.74−7.81(2H,m). IR(CHCl3):3262,3020,2948,2868,1708,1596,1511,140
7,1315,1242,1154,1091/cm. [α]D=+4.8゜(CHCl3,c=1.04,22℃). No.1a−129 CDCl3 300MHz 0.89−1.98(14H,m),2.18(1H,m),2.27(2H,t,J=7.2
Hz),2.99(1H,m),3.68(3H,s),3.79(3H,s),3.98
(2H,s),4.81(1H,d,J=6.6Hz),5.10−5.27(2H,m),
6.81−6.87(2H,m),7.03−7.10(2H,m),7.25−7.32
(2H,m),7.75−7.82(2H,m). IR(CHCl3):3382,3276,3006,2950,2874,1726,1609,150
9,1457,1436,1407,1315,1244,1154,1091,1033/cm. [α]D=+19.3゜(CHCl3,C=1.05,23℃). No.1a−130 CDCl3 300MHz 0.90−2.00(14H,m),2.20(1H,m),2.30(2H,t,J=7.2
Hz),2.98(1H,m),3.69(3H,s),4.81(1H,d,J=6.6H
z),5.12−5.32(2H,m),5.46(1H,brs),6.84−7.01
(6H,m),7.76−7.83(2H,m) IR(CHCl3):3380,3284,3024,2952,2874,1724,1588,150
4,1488,1436,1321,1296,1149,1091/cm. [α]D=+28.9゜(CHCl3,c=1.01,23℃). No.1a−131 CDCl3 300MHz 0.92−2.10(14H,m),2.18(1H,m),2.34(2H,t,J=6.9
Hz),2.96(1H,m),5.18−5.35(3H,m),6.84−7.01(6
H,m),7.75−7.83(2H,m). IR(CHCl3):3270,3028,2952,2874,1708,1589,1505,148
9,1456,1322,1297,1238,1148,1091/cm. [α]D=+7.7゜(CHCl3,C=1.09,24℃). No.1a−132 CDCl3 300MHz 0.91−2.02(14H,m),2.19(1H,m),2.29(2H,t,J=7.2
Hz),2.99(1H,m),3.68(3H,s),3.83(3H,s),4.82
(1H,d,J=6.6Hz),5.14−5.33(2H,m),6.90−7.04(6
H,m),7.76−7.83(2H,m). IR(CHCl3):3384,3006,2952,2874,1727,1589,1502,148
8,1459,1438,1321,1295,1231,1150,1092,1033/cm. [α]D=+3.1゜(CHCl3,C=1.01,23℃). No.1a−133 TLC Rf=0.21(酢酸エチル:n−ヘキサン=1:1(0.3%酢
酸)) No.1a−134 CDCl3 300MHz 0.97−2.10(14H,m),2.20(1H,m),2.36(2H,t,J=6.9
Hz),3.04(1H,m),5.22−5.33(2H,m),5.41(1H,d,J
=6.6Hz),7.02(1H,d,J=9.0Hz),7.09−7.13(2H,
m),7.26−7.32(1H,m),7.43−7.49(2H,m),7.93(1
H,d.d,J=2.4and9.0Hz),8.46(1H,d,J=2.4Hz). IR(CHCl3):3384,3270,3020,2958,1709,1610,1587,153
7,1479,1352,1271,1252,1167/cm. [α]D=+20.9゜(CHCl3,C=0.51,22℃). No.1a−135 CDCl3 300MHz 0.96−2.02(14H,m),2.21(1H,m),2.29(2H,t,J=7.2
Hz),3.07(1H,m),3.68(3H,s),5.04(1H,d,J=6.9H
z),5.16−5.33(2H,m),7.48−7.55(2H,m),7.64(1
H,m),7.76−7.82(2H,m),7.88−7.94(2H,m),7.98−
8.04(2H,m). IR(CHCl3):3384,3282,3026,2952,2874,1727,1663,159
6,1446,1396,1316,1274,1163,1090/cm. [α]D=+3.1゜(CHCl3,c=1.03,22.0℃)。
No.1a−136 CDCl3 300MHz 0.95−2.05(14H,m),2.19(1H,m),2.34(2H,t,J=7.2
Hz),3.08(1H,m),5.10−5.40(2H,m),5.35(1H,d,J
=6.8Hz),7.45−7.58(2H,m),7.64(1H,m),7.74−7.
84(2H,m),7.84−7.95(2H,m),7.95−8.06(2H,m). IR(CHCl3):3260,3018,2950,2870,1708,1662,1595,144
6,1395,1316,1274,1162,1090/cm. [α]D=+12.9゜(CHCl3,c=1.05,21.5℃)。
Hz),3.08(1H,m),5.10−5.40(2H,m),5.35(1H,d,J
=6.8Hz),7.45−7.58(2H,m),7.64(1H,m),7.74−7.
84(2H,m),7.84−7.95(2H,m),7.95−8.06(2H,m). IR(CHCl3):3260,3018,2950,2870,1708,1662,1595,144
6,1395,1316,1274,1162,1090/cm. [α]D=+12.9゜(CHCl3,c=1.05,21.5℃)。
No.1a−137 CDCl3 300MHz 0.97−2.04(14H,m),2.27(1H,m),2.31(2H,t,J=7.2
Hz),3.07(1H,m),3.70(3H,s),5.15−5.30(3H,m),
7.48−7.68(5H,m),7.96−8.02(2H,m). IR(CHCl3):3382,3030,2952,2878,1725,1446,1329,115
4,1098/cm. [α]D=−12.1゜(CHCl3,c=1.03,22.0℃)。
Hz),3.07(1H,m),3.70(3H,s),5.15−5.30(3H,m),
7.48−7.68(5H,m),7.96−8.02(2H,m). IR(CHCl3):3382,3030,2952,2878,1725,1446,1329,115
4,1098/cm. [α]D=−12.1゜(CHCl3,c=1.03,22.0℃)。
No.1a−138 CDCl3 300MHz 0.95−2.04(14H,m),2.25(1H,m),2.35(2H,t,J=7.2
Hz),3.08(1H,m),5.15−5.34(2H,m),5.41(1H,d,J
=6.6Hz),7.48−7.68(5H,m),7.98−8.03(2H,m). IR(CHCl3):3370,3242,3022,2950,2870,1707,1445,140
8,1329,1154,1099/cm. [α]D=−0.6゜(CHCl3,c=1.06,21.5℃)[α]365
+30.7゜(CHCl3,c=1.06,21.5℃)。
Hz),3.08(1H,m),5.15−5.34(2H,m),5.41(1H,d,J
=6.6Hz),7.48−7.68(5H,m),7.98−8.03(2H,m). IR(CHCl3):3370,3242,3022,2950,2870,1707,1445,140
8,1329,1154,1099/cm. [α]D=−0.6゜(CHCl3,c=1.06,21.5℃)[α]365
+30.7゜(CHCl3,c=1.06,21.5℃)。
No.1a−139 CDCl3 300MHz 0.92−2.19(14H,m),2.27−2.34(3H,m),3.26(1H,
m),3.65(3H,s),4.28(2H,s),4.37(1H,d,J=7.4H
z),5.34−5.50(2H,m),7.37−7.62(9H,m). IR(CHCl3):3389,3294,3028,3015,2954,2877,1730,160
0,1488,1325,1151,1129/cm. [α]D=−24.8゜(CHCl3,c=1.01,24℃)。
m),3.65(3H,s),4.28(2H,s),4.37(1H,d,J=7.4H
z),5.34−5.50(2H,m),7.37−7.62(9H,m). IR(CHCl3):3389,3294,3028,3015,2954,2877,1730,160
0,1488,1325,1151,1129/cm. [α]D=−24.8゜(CHCl3,c=1.01,24℃)。
No.1a−140 CDCl3 300MHz 0.92−2.22(15H,m),2.34(2H,t,J=7.1Hz),3.24(1
H,m),4.29(2H,s),4.81(1H,d,J=7.4Hz),5.32−5.5
2(2H,m),7.36−7.62(9H,m). IR(CHCl3):3510,3388,3251,3031,3015,2956,2877,266
8,1708,1601,1488,1318,1511,1129/cm. [α]D=−24.6゜(CHCl3,c=1.02,25℃)。
H,m),4.29(2H,s),4.81(1H,d,J=7.4Hz),5.32−5.5
2(2H,m),7.36−7.62(9H,m). IR(CHCl3):3510,3388,3251,3031,3015,2956,2877,266
8,1708,1601,1488,1318,1511,1129/cm. [α]D=−24.6゜(CHCl3,c=1.02,25℃)。
No.1a−141 CDCl3 300MHz 0.92−2.19(15H,m),2.32(2H,t,J=7.2Hz),3.26(1
H,m),3.65(3H,s),4.31(2H,s),4.48(1H,d,J=7.4H
z),5.33−5.49(2H,m),7.42−7.80(8H,m). IR(CHCl3):3388,3285,3018,2955,2877,2225,1730,159
7,1479,1320,1152,1129/cm. [α]D=−20.1゜(CHCl3),c=0.96,25℃). No.1a−142 CDCl3 300MHz 0.92−2.22(15H,m),2.35(2H,t,J=6.8Hz),3.25(1
H,m),4.32(2H,s),4.86(1H,d,J=7.4Hz),5.33−5.5
3(2H,m),7.43−7.80(8H,m). IR(CHCl3):3512,3388,3258,3031,3023,3014,2956 287
7,2225,1708,1597,1479,1319,1151,1128/cm. [α]D=−19.3゜(CHCl3,c=1.09,23℃). No.1a−143 CDCl3 300MHz 1.00−1.93(14H,m),2.17(1H,m),2.27(2H,t,J=7.2
Hz),3.07(1H,m),5.17−5.22(2H,m),5.36(1H,d,J
=6.9Hz),7.77(1H,d,J=9.0Hz),8.11−8.17(2H,
m),8.36(1H,d.d,J=2.1and9.0Hz),8.51(1H,d,J=1.
8Hz),8.65(1H,d,J=2.1Hz). IR(CHCl3):3382,3266,3026,2954,2874,1708,1632,158
5,1528,1458,1419,1345,1153/cm. [α]D=+7.6゜(CHCl3,C=1.04,22℃). No.1a−144 CDCl3 300MHz 0.95−1.90(14H,m),2.17(1H,m),2.25(2H,t,J=7.5
Hz),3.02(1H,m),5.09(1H,d,J=6.6Hz),5.15−5.21
(2H,m),6.72(1H,d,J=8.4Hz),6.85(1H,s),7.54
(1H,d,J=8.4Hz),7.72(1H,d,J=9.0Hz),7.83(1H,
d.d,J=1.8and9.0Hz),8.32(1H,d,J=1.8Hz). IR(CHCl3):3380,3260,3022,2948,2868,2352,1709,163
6,1460,1425,1313,1291,1265,1148,1130/cm. [α]D=+12.9゜(CHCl3,C=1.02,22.5℃). No.1a−145 CDCl3 300MHz 0.97−1.90(14H,m),2.15(1H,m),2.27(2H,t,J=6.9
Hz),3.02(1H,m),3.08(6H,s),5.12(1H,d,J=6.3H
z),5.19−5.25(2H,m),6.78−6.84(2H,m),7.53(1
H,d,J=8.7Hz),7.76−7.83(2H,m),8.30(1H,d,J=1.
8Hz). IR(CHCl3):3272,3030,2950,2874,1708,1635,1601,151
1,1457,1425,1357,1328,1151,1124/cm. [α]D=+6.3゜(CHCl3,C=1.04,23℃). No.1a−146 CDCl3 300MHz 0.95−2.00(14H,m),2.16(1H,m),2.29(2H,t,J=7.2
Hz),3.05(1H,m),4.10(3H,s),5.13−5.28(2H,m),
5.38(1H,d,J=6.9Hz),7.67−7.74(2H,m),8.08(1H,
d.d,J=1.8and9.0Hz),8.11(1H,s),8.61(1H,d,J=1.
8Hz). IR(CHCl3):3260,3020,2948,2868,1708,1639,1606,152
8,1470,1455,1424,1349,1311,1238,1174,1149,1120,107
9,1060,1022/cm. [α]D=+7.8゜(CHCl3,C=1.00,23℃). No.1a−147 CDCl3 300MHz 0.92−1.92(14H,m),2.17(1H,m),2.25(2H,t,J=7.2
Hz),3.01(1H,m),3.97(3H,s),5.10−5.27(5H,m),
6.92(1H,s),7.29(3H,s),7.52(1H,d,J=8.7Hz),7.
82(1H,d.d,J=2.1and8.7Hz),8.33(1H,d,J=2.1H
z). IR(CHCl3):3380,3264,3002,2950,2868,1708,1634,147
6,1452,1426,1317,1264,1218,1169,1147,1115,1068,103
1/cm. [α]D=+5.6゜(CHCl3,C=1.02,23℃). No.1a−148 CDCl3 300MHz 0.90−1.98(14H,m),2.15(1H,m),2.28(2H,t,J=6.9
Hz),2.91(6Hs),3.03(1H,m),4.01(3H,s),5.15−
5.26(3H,m),7.18(1H,s),7.38(1H,s),7.59(1H,d,
J=8.7Hz),7.87(1H,d.d,J=2.1and8.7Hz),8.40(1H,
d,J=2.1Hz). IR(CHCl3):3384,3266,2956,1709,1632,1602,1495,147
3,1458,1430,1317,1231,1148,1121/cm. [α]D=+11.2゜(CHCl3,C=1.01,23℃). No.1a−149 CDCl3 300MHz 0.99−1.90(14H,m),2.17(1H,m),2.28(2H,t,J=7.2
Hz),3.00(1H,m),5.13−5.19(2H,m),5.43(1H,d,J
=6.0Hz),7.02(1H,d.d,J=2.4and9.0Hz),7.38−7.41
(2H,m),7.58(1H,d,J=8.7Hz),7.96(1H,d.d,J=1.8
and8.7Hz),8.45(1H,d,J=1.8Hz). IR(CHCl3):3270,3020,2948,2868,1709,1601,1478,144
8,1419,1315,1147,1120/cm. [α]D=−11.4゜(CHCl3,C=1.01,23℃). No.1a−150 CDCl3 300MHz 0.97−1.88(14H,m),2.12−2.31(3H,m),2.38(3H,
s),3.01(1H,m),5.14−5.19(2H,m),5.36(1H,d,J=
6.6Hz),7.24(1H,d.d,J=2.4and9.0Hz),7.59(1H,d,J
=6.3Hz),7.66(1H,d,J=8.7Hz),7.72(1H,d,J=2.4H
z),8.01(1H,d.d,J=1.8and8.7Hz),8.49(1H,d,J=1.
8Hz). IR(CHCl3):3470,3374,3260,3018,2950,2868,1709,147
4,1444,1412,1370,1319,1266,1162,1145,1118/cm. [α]D=+4.9゜(CHCl3,C=1.00,24℃). No.1a−151 CDCl3 300MHz 0.97−1.89(14H,m),2.17(1H,m),2.25(2H,t,J=7.2
Hz),3.03(1H,m),3.92(3H,s),5.15−5.20(2H,m),
5.32(1H,d,J=6.6Hz),7.11(1H,d.d,J=2.4and9.3H
z),7.45(1H,d,J=2.4Hz),7.50(1H,d,J=9.3Hz),7.
62(1H,d,J=8.7Hz),7.97(1H,d.d,J=2.1and8.7Hz),
8.50(1H,d,J=2.1Hz). IR(CHCl3):3260,3018,2948,1708,1483,1454,1432,131
4,1287,1268,1188,1169,1147/cm. [α]D=+4.9゜(CHCl3,C=1.01,23.5℃). No.1a−152 CDCl3 300MHz 0.98−2.04(14H,m),2.15(1H,m),2.30(2H,t,J=6.6
Hz),3.04(1H,m),5.17−5.29(3H,m),7.41(1H,d.d,
J=1.5and8.1Hz),7.64−7.68(2H,m),7.92(1H,d,J=
8.4Hz),8.00(1H,d.d,J=1.8and8.4Hz),8.49(1H,d,J
=1.8Hz). IR(CHCl3):3266,3028,2952,2872,1707,1629,1591,145
6,1416,1318,1275,1150/cm. [α]D=+3.2゜(CHCl3,C=1.04,23℃). No.1a−153 CDCl3 300MHz 0.97−1.88(14H,m),2.16(1H,m),2.26(2H,t,J=7.2
Hz),3.03(1H,m),4.64−4.65(2H,m),5.16−5.50(5
H,m),6.13(1H,m),7.14(1H,d.d,J=2.7and9.0Hz),
7.46−7.52(2H,m),7.63(1H,d,J=8.7Hz),7.97(1H,
d.d,J=1.8and8.7Hz),8.49(1H,d,J=1.8Hz). IR(CHCl3):3374,3260,3020,2948,2868,1708,1599,147
8,1446,1414,1314,1284,1268,1184,1148,1120/cm. [α]D=+5.3゜(CHCl3,C=1.00,23℃). No.1a−154 CDCl3 300MHz 0.99−2.00(15H,m),2.26(2H,t,J=7.2Hz),3.03(1
H,m),4.07(3H,s),5.23−5.27(2H,m),5.36(1H,d,J
=7.2Hz),7.20(1H,s),7.36−7.48(2H,m),7.55−7.
58(1H,m),7.91−7.93(1H,m),8.52(1H,s). IR(CHCl3):3362,3257,3020,2948,2868,1708,1637,160
2,1579,1488,1457,1437,1413,1345,1318,1301,1276,118
2,1104/cm. [α]D=+19.4゜(CHCl3,C=1.01,25℃). mp.88−90℃ No.1a−155 CDCl3 300MHz 0.92−2.02(14H,m),2.15(1H,m),2.31(2H,t,J=7.2
Hz),3.01(1H,m),4.10(2H,s),5.10(1H,d,J=6.6H
z),5.18−5.35(2H,m),7.04−7.26(5H,m),7.67−7.
76(2H,m). IR(CHCl3):3266,3028,2952,2952,2872,1708,1599,157
4,1478,1457,1418,1301,1258,1147,1124,1101,1080/cm. [α]365+33.4゜(CHCl3,C=1.00,23℃). No.1a−156 CDCl3 300MHz 0.91−2.21(15H,m),2.33(2H,t,J=6.9Hz),3.01(1
H,m),5.11(1H,d,J=6.6Hz),5.27−5.35(2H,m),6.8
5−6.96(5H,m),7.35(1H,d,J=2.1Hz),7.42(1H,d.
d,J=2.1and8.7Hz). IR(CHCl3):3384,3263,2957,1708,1587,1489,1462,141
6,1290,1222,1151,1123/cm. [α]D=+6.4゜(CHCl3,C=1.00,23℃). No.1a−157 CDCl3 300MHz 0.97−1.91(14H,m),2.18(1H,m),2.26(2H,t,J=6.9
Hz),3.04(1H,m),5.18−5.26(3H,m),7.52−7.56(2
H,m),7.88−8.00(3H,m),8.25(1H,m),8.69(1H,
m). IR(CHCl3):3382,3268,2952,2874,1707,1457,1425,140
9,1318,1152/cm. [α]D=+4.4゜(CHCl3,C=1.02,22℃). No.1a−158 CDCl3 300MHz 1.02−1.97(14H,m),2.20(1H,m),2.29(2H,t,J=7.2
Hz),3.06(1H,m),5.19−5.24(2H,m),5.58(1H,d,J,
6.6Hz),7.62(1H,m),7.72(1H,m),7.86−7.91(2H,
m),7.96(1H,d,J=7.8Hz),8.04(1H,d.d,J=1.5and8.
1Hz),8.34(1H,d,J=1.2Hz). IR(CHCl3):3490,3260,3020,2950,2870,1707,1456,139
9,1312,1165/cm. [α]D=−8.3゜(CHCl3,C=1.00,23℃). No.1a−159 CDCl3 300MHz 0.92−1.88(14H,m),2.13(1H,m),2.24(2H,m),3.02
(1H,m),3.90(3H,s),5.12−5.26(3H,m),7.29−7.5
8(4H,m),7.97(1H,d.d,J=1.8and7.5Hz),8.13(1H,
d,J=7.5Hz),8.64(1H,d,J=1.8Hz). IR(CHCl3):3382,3266,3018,2956,1708,1629,1594,147
6,1467,1325,1245,1227,1158,11146/cm. [α]D=+14.6゜(CHCl3,C=1.00,22℃). No.1a−160 CDCl3 300MHz 0.93−1.88(14H,m),2.18−2.24(3H,m),3.00(1H,
m),5.08−5.21(3H,m),7.28−7.33(1H,m),7.47−7.
51(3H,m),7.90(1H,d.d,J=1.5and7.8Hz),8.10(1H,
d,J=7.8Hz),8.63−8.64(2H,m). IR(CHCl3):3465,3380,3275,3020,2957,2876,1708,162
7,1604,1495,1473,1457,1328,1240,1222,1156,1149/cm. [α]D=+8.2゜(CHCl3,C=1.01,22℃). No.1a−161 CDCl3 300MHz 0.98−1.88(14H,m),2.17(1H,m),2.24(2H,t,J=7.2
Hz),3.05(1H,m),5.16−5.20(2H,m),5.35(1H,d,J
=6.6Hz),7.40(1H,m),7.55(1H,m),7.63(1H,d,J=
8.1Hz),7.89(1H,d.d,J=1.5and8.1Hz),8.01(1H,
m),8.06(1H,d,J=8.1Hz),8.12(1H,d,J=1.5Hz). IR(CHCl3):3478,3266,3028,2952,2874,1708,1454,141
7,1323,1196,1148/cm. [α]D=+21.9゜(CHCl3,C=1.01,23℃). No.1a−162 CDCl3 300MHz 0.96−1.98(14H,m),2.02(1H,m),2.25(2H,t,J=7.2
Hz),3.05(1H,m),4.10(3H,s),5.14−5.25(2H,m),
5.41(1H,d,J=7.2Hz),7.35−7.42(1H,m),7.51−7.6
4(3H,m),7.94−8.00(1H,m),8.16(1H,s). IR(CHCl3):3368,3274,3028,2952,2874,1708,1633,158
3,1465,1452,1438,1413,1315,1151,1103,1053,1024/cm. [α]D=+15.1゜(CHCl3,C=1.01,23℃).mp.108−1
10℃ No.1a−163 d6−DMSO 300MHz 0.97−1.84(14H,m),1.92(1H,m),2.04(2H,t,J=7.2
Hz),2.90(1H,m),5.08−5.23(2H,m),7.32(1H,s),
7.38−7.61(2H,m),7.62(1H,s),7.68−7.71(1H,
m),7.92(1H,s),8.14−8.17(1H,m),10.7(1H,s),1
1.9(1H,s). IR(KBr):3350,3295,2952,2874,1707,1636,1601,1466,
1431,1389,1315,1251,1174,1146,1106/cm. [α]D=−25.3゜(CH30H,C=1.01,25℃).mp.159−1
62℃ No.1a−164 CDCl3 300MHz 0.98−1.96(17H,m),2.05(1H,m),2.25(2H,t,J=7.2
Hz),3.07(1H,m),4.32(2H,q,J=7.2Hz),5.19−5.23
(2H,m),5.31(1H,d,J=7.8Hz),7.38(1H,m),7.41−
7.62(3H,m),7.95(1H,m),8.15(1H,s). IR(CHCl3):3360,3018,2946,2870,1709,1633,1457,144
5,1425,1394,1314,1176,1152,1105/cm. [α]D=+12.7゜(CHCl3,C=1.02,25℃).mp.108−1
09℃ No.1a−165 CDCl3 300MHz 0.95−1.98(15H,m),2.26(2H,t,J=7.5Hz),3.04(1
H,m),4.15(3H,s),5.20−5.26(2H,m),5.34(1H,d,J
=6.9Hz),7.41−7.47(1H,m),7.65−7.68(2H,m),7.
89−7.92(1H,m),8.32(1H,s). IR(CHCl3):3366,3087,3022,2957,1708,1632,1538,146
3,1408,1364,1346,1308,1227,1212,1205,1167/cm. [α]D=+19.6゜(CHCl3,C=1.01,25℃). No.1a−166 CDCl3 300MHz 0.97−2.02(15H,m),2.27(2H,t,J=6.9Hz),3.07(1
H,m),4.14(3H,s),5.21−5.27(2H,m),5.47(1H,d,J
=6.9Hz),7.64(1H,s),7.72(1H,d.d,J=0.6and9.0H
z),8.25(1H,s),8.47(1H,d.d,J=2.4and9.0Hz),8.9
4(1H,d.d,J=0.6and2.4Hz). IR(CHCl3):3373,2957,1708,1639,1587,1528,1467,142
8,1415,1345,1221,1184,1155/cm. [α]D=+14.4゜(CHCl3,C=0.50,25℃) No.1a−167 CDCl3 300MHz 0.92−2.00(14H,m),2.15(1H,m),2.27(2H,t,J=7.2
Hz),3.04(1H,m),3.97(2H,s),5.15−5.30(3H,m),
7.35−7.47(2H,m),7.55−7.63(1H,m),7.80−7.96
(3H,m),8.05(1H,d,J=0.3Hz). IR(CHCl3):3260,3020,2948,2868,1707,1451,1413,131
9,1172,1144,1101,1071/cm. [α]D=+18.2゜(CHCl3,C=1.04,22℃). No.1a−168 CDCl3 300MHz 0.90−1.88(14H,m),2.16(1H,m),2.25(2H,t,J=6.9
Hz),3.00(1H,m),5.00−5.19(2H,m),5.35(1H,d,J
=6.6Hz),7.25−7.30(1H,m),7.48−7.50(2H,m),7.
73(1H,d.d,J=1.5and8.1Hz),8.08−8.14(3H,m),8.9
3(1H,s). IR(CHCl3):3466,3380,3276,3016,2957,1708,1630,149
5,1458,1324,1241,1150/cm. [α]D=+18.0゜(CHCl3,C=1.00,22℃). No.1a−169 CDCl3 300MHz 0.87−1.86(14H,m),2.15(1H,m),2.25(2H,t,J=6.9
Hz),2.98(1H,m),3.89(3H,s),5.00−5.22(2H,m),
5.27(1H,d,J=6.9Hz),6.88(1H,d.d,J=2.1and8.4H
z),6.94(1H,d,J=2.1Hz),7.69(1H,d.d,J=1.5and7.
8Hz),7.92−8.01(3H,m),8.83(1H,s). IR(CHCl3):3465,3378,3276,3022,2957,1708,1630,160
9,1569,1459,1433,1314,1281,1229,1151/cm. [α]D=+19.3゜(CHCl3,C=1.01,21℃). No.1a−170 CDCl3 300MHz 0.88−2.25(17H,m),3.04(1H,m),3.84(3H,s),3.95
(3H,s),5.06−5.26(3H,m),6.87−6.93(2H,m),7.6
9(1H,d.d,J=1.6and8.2Hz),7.93−9.05(3H,m). IR(CHCl3):3026,2957,1708,1630,1601,1460,1331,124
3,1224,1152/cm. [α]D=+17.2゜(CHCl3,C=1.00,22℃). No.1a−171 CDCl3 300MHz 0.95−2.00(14H,m),2.16−2.32(3H,m),2.66(3H,
s),3.14(1H,m),3.68(3H,s),5.09(1H,d,J=6.8H
z),5.10−5.28(2H,m),7.45(1H,d.d,J=1.8&8.6H
z),7.75−7.84(2H,m). IR(CHCl3):3374,3018,2946,2868,1725,1585,1513,143
6,1340,1278,1153,1112/cm. [α]D=−14.7゜(CHCl3,c=1.07,25.0℃)。
H,m),3.65(3H,s),4.31(2H,s),4.48(1H,d,J=7.4H
z),5.33−5.49(2H,m),7.42−7.80(8H,m). IR(CHCl3):3388,3285,3018,2955,2877,2225,1730,159
7,1479,1320,1152,1129/cm. [α]D=−20.1゜(CHCl3),c=0.96,25℃). No.1a−142 CDCl3 300MHz 0.92−2.22(15H,m),2.35(2H,t,J=6.8Hz),3.25(1
H,m),4.32(2H,s),4.86(1H,d,J=7.4Hz),5.33−5.5
3(2H,m),7.43−7.80(8H,m). IR(CHCl3):3512,3388,3258,3031,3023,3014,2956 287
7,2225,1708,1597,1479,1319,1151,1128/cm. [α]D=−19.3゜(CHCl3,c=1.09,23℃). No.1a−143 CDCl3 300MHz 1.00−1.93(14H,m),2.17(1H,m),2.27(2H,t,J=7.2
Hz),3.07(1H,m),5.17−5.22(2H,m),5.36(1H,d,J
=6.9Hz),7.77(1H,d,J=9.0Hz),8.11−8.17(2H,
m),8.36(1H,d.d,J=2.1and9.0Hz),8.51(1H,d,J=1.
8Hz),8.65(1H,d,J=2.1Hz). IR(CHCl3):3382,3266,3026,2954,2874,1708,1632,158
5,1528,1458,1419,1345,1153/cm. [α]D=+7.6゜(CHCl3,C=1.04,22℃). No.1a−144 CDCl3 300MHz 0.95−1.90(14H,m),2.17(1H,m),2.25(2H,t,J=7.5
Hz),3.02(1H,m),5.09(1H,d,J=6.6Hz),5.15−5.21
(2H,m),6.72(1H,d,J=8.4Hz),6.85(1H,s),7.54
(1H,d,J=8.4Hz),7.72(1H,d,J=9.0Hz),7.83(1H,
d.d,J=1.8and9.0Hz),8.32(1H,d,J=1.8Hz). IR(CHCl3):3380,3260,3022,2948,2868,2352,1709,163
6,1460,1425,1313,1291,1265,1148,1130/cm. [α]D=+12.9゜(CHCl3,C=1.02,22.5℃). No.1a−145 CDCl3 300MHz 0.97−1.90(14H,m),2.15(1H,m),2.27(2H,t,J=6.9
Hz),3.02(1H,m),3.08(6H,s),5.12(1H,d,J=6.3H
z),5.19−5.25(2H,m),6.78−6.84(2H,m),7.53(1
H,d,J=8.7Hz),7.76−7.83(2H,m),8.30(1H,d,J=1.
8Hz). IR(CHCl3):3272,3030,2950,2874,1708,1635,1601,151
1,1457,1425,1357,1328,1151,1124/cm. [α]D=+6.3゜(CHCl3,C=1.04,23℃). No.1a−146 CDCl3 300MHz 0.95−2.00(14H,m),2.16(1H,m),2.29(2H,t,J=7.2
Hz),3.05(1H,m),4.10(3H,s),5.13−5.28(2H,m),
5.38(1H,d,J=6.9Hz),7.67−7.74(2H,m),8.08(1H,
d.d,J=1.8and9.0Hz),8.11(1H,s),8.61(1H,d,J=1.
8Hz). IR(CHCl3):3260,3020,2948,2868,1708,1639,1606,152
8,1470,1455,1424,1349,1311,1238,1174,1149,1120,107
9,1060,1022/cm. [α]D=+7.8゜(CHCl3,C=1.00,23℃). No.1a−147 CDCl3 300MHz 0.92−1.92(14H,m),2.17(1H,m),2.25(2H,t,J=7.2
Hz),3.01(1H,m),3.97(3H,s),5.10−5.27(5H,m),
6.92(1H,s),7.29(3H,s),7.52(1H,d,J=8.7Hz),7.
82(1H,d.d,J=2.1and8.7Hz),8.33(1H,d,J=2.1H
z). IR(CHCl3):3380,3264,3002,2950,2868,1708,1634,147
6,1452,1426,1317,1264,1218,1169,1147,1115,1068,103
1/cm. [α]D=+5.6゜(CHCl3,C=1.02,23℃). No.1a−148 CDCl3 300MHz 0.90−1.98(14H,m),2.15(1H,m),2.28(2H,t,J=6.9
Hz),2.91(6Hs),3.03(1H,m),4.01(3H,s),5.15−
5.26(3H,m),7.18(1H,s),7.38(1H,s),7.59(1H,d,
J=8.7Hz),7.87(1H,d.d,J=2.1and8.7Hz),8.40(1H,
d,J=2.1Hz). IR(CHCl3):3384,3266,2956,1709,1632,1602,1495,147
3,1458,1430,1317,1231,1148,1121/cm. [α]D=+11.2゜(CHCl3,C=1.01,23℃). No.1a−149 CDCl3 300MHz 0.99−1.90(14H,m),2.17(1H,m),2.28(2H,t,J=7.2
Hz),3.00(1H,m),5.13−5.19(2H,m),5.43(1H,d,J
=6.0Hz),7.02(1H,d.d,J=2.4and9.0Hz),7.38−7.41
(2H,m),7.58(1H,d,J=8.7Hz),7.96(1H,d.d,J=1.8
and8.7Hz),8.45(1H,d,J=1.8Hz). IR(CHCl3):3270,3020,2948,2868,1709,1601,1478,144
8,1419,1315,1147,1120/cm. [α]D=−11.4゜(CHCl3,C=1.01,23℃). No.1a−150 CDCl3 300MHz 0.97−1.88(14H,m),2.12−2.31(3H,m),2.38(3H,
s),3.01(1H,m),5.14−5.19(2H,m),5.36(1H,d,J=
6.6Hz),7.24(1H,d.d,J=2.4and9.0Hz),7.59(1H,d,J
=6.3Hz),7.66(1H,d,J=8.7Hz),7.72(1H,d,J=2.4H
z),8.01(1H,d.d,J=1.8and8.7Hz),8.49(1H,d,J=1.
8Hz). IR(CHCl3):3470,3374,3260,3018,2950,2868,1709,147
4,1444,1412,1370,1319,1266,1162,1145,1118/cm. [α]D=+4.9゜(CHCl3,C=1.00,24℃). No.1a−151 CDCl3 300MHz 0.97−1.89(14H,m),2.17(1H,m),2.25(2H,t,J=7.2
Hz),3.03(1H,m),3.92(3H,s),5.15−5.20(2H,m),
5.32(1H,d,J=6.6Hz),7.11(1H,d.d,J=2.4and9.3H
z),7.45(1H,d,J=2.4Hz),7.50(1H,d,J=9.3Hz),7.
62(1H,d,J=8.7Hz),7.97(1H,d.d,J=2.1and8.7Hz),
8.50(1H,d,J=2.1Hz). IR(CHCl3):3260,3018,2948,1708,1483,1454,1432,131
4,1287,1268,1188,1169,1147/cm. [α]D=+4.9゜(CHCl3,C=1.01,23.5℃). No.1a−152 CDCl3 300MHz 0.98−2.04(14H,m),2.15(1H,m),2.30(2H,t,J=6.6
Hz),3.04(1H,m),5.17−5.29(3H,m),7.41(1H,d.d,
J=1.5and8.1Hz),7.64−7.68(2H,m),7.92(1H,d,J=
8.4Hz),8.00(1H,d.d,J=1.8and8.4Hz),8.49(1H,d,J
=1.8Hz). IR(CHCl3):3266,3028,2952,2872,1707,1629,1591,145
6,1416,1318,1275,1150/cm. [α]D=+3.2゜(CHCl3,C=1.04,23℃). No.1a−153 CDCl3 300MHz 0.97−1.88(14H,m),2.16(1H,m),2.26(2H,t,J=7.2
Hz),3.03(1H,m),4.64−4.65(2H,m),5.16−5.50(5
H,m),6.13(1H,m),7.14(1H,d.d,J=2.7and9.0Hz),
7.46−7.52(2H,m),7.63(1H,d,J=8.7Hz),7.97(1H,
d.d,J=1.8and8.7Hz),8.49(1H,d,J=1.8Hz). IR(CHCl3):3374,3260,3020,2948,2868,1708,1599,147
8,1446,1414,1314,1284,1268,1184,1148,1120/cm. [α]D=+5.3゜(CHCl3,C=1.00,23℃). No.1a−154 CDCl3 300MHz 0.99−2.00(15H,m),2.26(2H,t,J=7.2Hz),3.03(1
H,m),4.07(3H,s),5.23−5.27(2H,m),5.36(1H,d,J
=7.2Hz),7.20(1H,s),7.36−7.48(2H,m),7.55−7.
58(1H,m),7.91−7.93(1H,m),8.52(1H,s). IR(CHCl3):3362,3257,3020,2948,2868,1708,1637,160
2,1579,1488,1457,1437,1413,1345,1318,1301,1276,118
2,1104/cm. [α]D=+19.4゜(CHCl3,C=1.01,25℃). mp.88−90℃ No.1a−155 CDCl3 300MHz 0.92−2.02(14H,m),2.15(1H,m),2.31(2H,t,J=7.2
Hz),3.01(1H,m),4.10(2H,s),5.10(1H,d,J=6.6H
z),5.18−5.35(2H,m),7.04−7.26(5H,m),7.67−7.
76(2H,m). IR(CHCl3):3266,3028,2952,2952,2872,1708,1599,157
4,1478,1457,1418,1301,1258,1147,1124,1101,1080/cm. [α]365+33.4゜(CHCl3,C=1.00,23℃). No.1a−156 CDCl3 300MHz 0.91−2.21(15H,m),2.33(2H,t,J=6.9Hz),3.01(1
H,m),5.11(1H,d,J=6.6Hz),5.27−5.35(2H,m),6.8
5−6.96(5H,m),7.35(1H,d,J=2.1Hz),7.42(1H,d.
d,J=2.1and8.7Hz). IR(CHCl3):3384,3263,2957,1708,1587,1489,1462,141
6,1290,1222,1151,1123/cm. [α]D=+6.4゜(CHCl3,C=1.00,23℃). No.1a−157 CDCl3 300MHz 0.97−1.91(14H,m),2.18(1H,m),2.26(2H,t,J=6.9
Hz),3.04(1H,m),5.18−5.26(3H,m),7.52−7.56(2
H,m),7.88−8.00(3H,m),8.25(1H,m),8.69(1H,
m). IR(CHCl3):3382,3268,2952,2874,1707,1457,1425,140
9,1318,1152/cm. [α]D=+4.4゜(CHCl3,C=1.02,22℃). No.1a−158 CDCl3 300MHz 1.02−1.97(14H,m),2.20(1H,m),2.29(2H,t,J=7.2
Hz),3.06(1H,m),5.19−5.24(2H,m),5.58(1H,d,J,
6.6Hz),7.62(1H,m),7.72(1H,m),7.86−7.91(2H,
m),7.96(1H,d,J=7.8Hz),8.04(1H,d.d,J=1.5and8.
1Hz),8.34(1H,d,J=1.2Hz). IR(CHCl3):3490,3260,3020,2950,2870,1707,1456,139
9,1312,1165/cm. [α]D=−8.3゜(CHCl3,C=1.00,23℃). No.1a−159 CDCl3 300MHz 0.92−1.88(14H,m),2.13(1H,m),2.24(2H,m),3.02
(1H,m),3.90(3H,s),5.12−5.26(3H,m),7.29−7.5
8(4H,m),7.97(1H,d.d,J=1.8and7.5Hz),8.13(1H,
d,J=7.5Hz),8.64(1H,d,J=1.8Hz). IR(CHCl3):3382,3266,3018,2956,1708,1629,1594,147
6,1467,1325,1245,1227,1158,11146/cm. [α]D=+14.6゜(CHCl3,C=1.00,22℃). No.1a−160 CDCl3 300MHz 0.93−1.88(14H,m),2.18−2.24(3H,m),3.00(1H,
m),5.08−5.21(3H,m),7.28−7.33(1H,m),7.47−7.
51(3H,m),7.90(1H,d.d,J=1.5and7.8Hz),8.10(1H,
d,J=7.8Hz),8.63−8.64(2H,m). IR(CHCl3):3465,3380,3275,3020,2957,2876,1708,162
7,1604,1495,1473,1457,1328,1240,1222,1156,1149/cm. [α]D=+8.2゜(CHCl3,C=1.01,22℃). No.1a−161 CDCl3 300MHz 0.98−1.88(14H,m),2.17(1H,m),2.24(2H,t,J=7.2
Hz),3.05(1H,m),5.16−5.20(2H,m),5.35(1H,d,J
=6.6Hz),7.40(1H,m),7.55(1H,m),7.63(1H,d,J=
8.1Hz),7.89(1H,d.d,J=1.5and8.1Hz),8.01(1H,
m),8.06(1H,d,J=8.1Hz),8.12(1H,d,J=1.5Hz). IR(CHCl3):3478,3266,3028,2952,2874,1708,1454,141
7,1323,1196,1148/cm. [α]D=+21.9゜(CHCl3,C=1.01,23℃). No.1a−162 CDCl3 300MHz 0.96−1.98(14H,m),2.02(1H,m),2.25(2H,t,J=7.2
Hz),3.05(1H,m),4.10(3H,s),5.14−5.25(2H,m),
5.41(1H,d,J=7.2Hz),7.35−7.42(1H,m),7.51−7.6
4(3H,m),7.94−8.00(1H,m),8.16(1H,s). IR(CHCl3):3368,3274,3028,2952,2874,1708,1633,158
3,1465,1452,1438,1413,1315,1151,1103,1053,1024/cm. [α]D=+15.1゜(CHCl3,C=1.01,23℃).mp.108−1
10℃ No.1a−163 d6−DMSO 300MHz 0.97−1.84(14H,m),1.92(1H,m),2.04(2H,t,J=7.2
Hz),2.90(1H,m),5.08−5.23(2H,m),7.32(1H,s),
7.38−7.61(2H,m),7.62(1H,s),7.68−7.71(1H,
m),7.92(1H,s),8.14−8.17(1H,m),10.7(1H,s),1
1.9(1H,s). IR(KBr):3350,3295,2952,2874,1707,1636,1601,1466,
1431,1389,1315,1251,1174,1146,1106/cm. [α]D=−25.3゜(CH30H,C=1.01,25℃).mp.159−1
62℃ No.1a−164 CDCl3 300MHz 0.98−1.96(17H,m),2.05(1H,m),2.25(2H,t,J=7.2
Hz),3.07(1H,m),4.32(2H,q,J=7.2Hz),5.19−5.23
(2H,m),5.31(1H,d,J=7.8Hz),7.38(1H,m),7.41−
7.62(3H,m),7.95(1H,m),8.15(1H,s). IR(CHCl3):3360,3018,2946,2870,1709,1633,1457,144
5,1425,1394,1314,1176,1152,1105/cm. [α]D=+12.7゜(CHCl3,C=1.02,25℃).mp.108−1
09℃ No.1a−165 CDCl3 300MHz 0.95−1.98(15H,m),2.26(2H,t,J=7.5Hz),3.04(1
H,m),4.15(3H,s),5.20−5.26(2H,m),5.34(1H,d,J
=6.9Hz),7.41−7.47(1H,m),7.65−7.68(2H,m),7.
89−7.92(1H,m),8.32(1H,s). IR(CHCl3):3366,3087,3022,2957,1708,1632,1538,146
3,1408,1364,1346,1308,1227,1212,1205,1167/cm. [α]D=+19.6゜(CHCl3,C=1.01,25℃). No.1a−166 CDCl3 300MHz 0.97−2.02(15H,m),2.27(2H,t,J=6.9Hz),3.07(1
H,m),4.14(3H,s),5.21−5.27(2H,m),5.47(1H,d,J
=6.9Hz),7.64(1H,s),7.72(1H,d.d,J=0.6and9.0H
z),8.25(1H,s),8.47(1H,d.d,J=2.4and9.0Hz),8.9
4(1H,d.d,J=0.6and2.4Hz). IR(CHCl3):3373,2957,1708,1639,1587,1528,1467,142
8,1415,1345,1221,1184,1155/cm. [α]D=+14.4゜(CHCl3,C=0.50,25℃) No.1a−167 CDCl3 300MHz 0.92−2.00(14H,m),2.15(1H,m),2.27(2H,t,J=7.2
Hz),3.04(1H,m),3.97(2H,s),5.15−5.30(3H,m),
7.35−7.47(2H,m),7.55−7.63(1H,m),7.80−7.96
(3H,m),8.05(1H,d,J=0.3Hz). IR(CHCl3):3260,3020,2948,2868,1707,1451,1413,131
9,1172,1144,1101,1071/cm. [α]D=+18.2゜(CHCl3,C=1.04,22℃). No.1a−168 CDCl3 300MHz 0.90−1.88(14H,m),2.16(1H,m),2.25(2H,t,J=6.9
Hz),3.00(1H,m),5.00−5.19(2H,m),5.35(1H,d,J
=6.6Hz),7.25−7.30(1H,m),7.48−7.50(2H,m),7.
73(1H,d.d,J=1.5and8.1Hz),8.08−8.14(3H,m),8.9
3(1H,s). IR(CHCl3):3466,3380,3276,3016,2957,1708,1630,149
5,1458,1324,1241,1150/cm. [α]D=+18.0゜(CHCl3,C=1.00,22℃). No.1a−169 CDCl3 300MHz 0.87−1.86(14H,m),2.15(1H,m),2.25(2H,t,J=6.9
Hz),2.98(1H,m),3.89(3H,s),5.00−5.22(2H,m),
5.27(1H,d,J=6.9Hz),6.88(1H,d.d,J=2.1and8.4H
z),6.94(1H,d,J=2.1Hz),7.69(1H,d.d,J=1.5and7.
8Hz),7.92−8.01(3H,m),8.83(1H,s). IR(CHCl3):3465,3378,3276,3022,2957,1708,1630,160
9,1569,1459,1433,1314,1281,1229,1151/cm. [α]D=+19.3゜(CHCl3,C=1.01,21℃). No.1a−170 CDCl3 300MHz 0.88−2.25(17H,m),3.04(1H,m),3.84(3H,s),3.95
(3H,s),5.06−5.26(3H,m),6.87−6.93(2H,m),7.6
9(1H,d.d,J=1.6and8.2Hz),7.93−9.05(3H,m). IR(CHCl3):3026,2957,1708,1630,1601,1460,1331,124
3,1224,1152/cm. [α]D=+17.2゜(CHCl3,C=1.00,22℃). No.1a−171 CDCl3 300MHz 0.95−2.00(14H,m),2.16−2.32(3H,m),2.66(3H,
s),3.14(1H,m),3.68(3H,s),5.09(1H,d,J=6.8H
z),5.10−5.28(2H,m),7.45(1H,d.d,J=1.8&8.6H
z),7.75−7.84(2H,m). IR(CHCl3):3374,3018,2946,2868,1725,1585,1513,143
6,1340,1278,1153,1112/cm. [α]D=−14.7゜(CHCl3,c=1.07,25.0℃)。
No.1a−172 CDCl3 300MHz 0.97−2.02(14H,m),2.23(1H,m),2.28(2H,t,J=7.2
Hz),2.66(3H,s),3.14(1H,m),5.12−5.22(2H,m),
5.41(1H,d,J=7.2Hz),7.45(1H,d.d,J=2.1&8.7H
z),7.76(1H,d,J=8.7Hz),7.78(1H,d,J=2.1Hz). IR(CHCl3):3372,3250,3022,2950,2868,1707,1514,141
9,1336,1279,1154,1112/cm. [α]D=−4.1゜(CHCl3,C=1.08,26.0℃)m.p.141−
143℃ No.1a−173 CDCl3 300MHz 1.15−2.42(17H,m),2.91(1H,m),5.15(1H,d,J=4.2
Hz),5.25−5.40(2H,m),7.85(1H,d,J=7.2Hz),8.00
(1H,d,J=8.1Hz),8.15−8.20(2H,m),8.67(1H,d,J
=8.1Hz),8.73(1H,d,J=8.1Hz),8.83(1H,s),9.43
(1H,s). IR(KBr):3422,3269,3046,2952,2871,1711,1617,1447,
1333,1243,1161,1146/cm. [α]D=−41.0゜(CH30H,C=1.01,23℃). No.1a−174 CDCl3+d6−DMSO 300MHz 1.00−1.92(14H,m),2.20(2H,t,J=6.6Hz),2.35(1
H,m),2.92(1H,m),5.05−5.22(2H,m),6.63(1H,d,J
=5.4Hz),7.77−7.92(3H,m),8.31(1H,d.d,J=1.8an
d8.7Hz),8.59(1H,d,J=8.7Hz),8.73(1H,d,J=8.7H
z),9.01(1H,s),9.55(1H,d,J=1.8Hz). IR(KBr):3433,3252,2952,2871,1696,1578,1423,1335,
1308,1219,1185,1160,1106/cm. [α]D=−19.3゜(DMSO,C=0.50,23℃). No.1a−175 CDCl3 300MHz 0.96−1.87(14H,m),2.20−2.25(3H,m),2.95(1H,
m),3.66(3H,s),4.74(1H,d,J=6.6Hz),5.10−5.12
(2H,m),6.88(1H,d,J=1.2Hz),7.37−7.50(3H,m),
7.56(1H,dd,J=8.7,1.5Hz),7.68−7.77(3H,m),8.06
(1H,s),9.44(1H,dd,J=1.2Hz). IR(CHCl3):3462,3374,3026,3006,2952,2872,1724,161
0,1580,1484,1452,1358,1309,1147. [α]D=+16.4゜(CHCl3,c=1.05,26℃).mp.130−1
32℃. No.1a−176 CDCl3+CD3OD 300MHz 1.00−2.02(14H,m),2.22(1H,m),2.29(2H,t,J=6.9
Hz),2.88(1H,m),5.16−5.26(2H,m),6.87(1H,s),
7.28−7.57(4H,m),7.69(1H,d,J=8.4Hz),7.75−7.7
8(2H,m),7.99(1H,s). IR(KBr):3254,2944,1704,1484,1453,1358,1305,1147. [α]D=+13.0゜(CH3OH,c=1.02,24℃),mp.160−1
61℃ No.1a−177 CDCl3 300MHz 0.96−1.88(14H,m),1.88−2.26(3H,m),2.94(1H,
m),3.67(3H,s),3.87(3H,s),4.67(1H,brs),5.08
−5.14(2H,m),6.77(1H,d,J=1.5Hz),6.99−7.02(2
H,m),7.53−7.57(1H,m),7.65−7.70(3H,m),8.00
(1H,s),9.27(1H,brs). IR(CHCl3):3426,3376,3006,2952,1724,1610,1495,143
8,1357,1308,1282,1249,1177,1147/cm. [α]D=+18.1゜(CHCl3,C=1.02,22℃). No.1a−178 CDCl3+CD3OD 300MHz 0.96−1.91(14H,m),2.19(1H,m),2.27(2H,t,J=6.0
Hz),2.85(1H,m),3.87(3H,s),5.16−5.23(2H,m),
6.99−7.02(2H,m),7.41(1H,m),7.64−7.73(3H,
m),7.92(1H,m). IR(CHCl3):3366,3261,3004,2954,2873,1705,1611,149
6,1458,1438,1304,1286,1253,1180,1149,1128/cm. [α]D=+14.6゜(CHCl3,C=1.02,22℃). No.1a−179 CDCl3+CD3OD 300MHz 0.96−1.87(14H,m),2.15−2.23(3H,m),2.93(1H,
m),3.85(3H,s),5.10−5.16(2H,m),6.90−6.93(2
H,m),7.50(1H,m),7.60−7.65(3H,m),7.91(1H,d,J
=0.9Hz). IR(CHCl3):3369,3270,2950,2873,1719,1612,1498,145
6,1440,1359,1306,1269,1219,1146,1127/cm. [α]D=+18.1゜(CH3OH,C=1.00,22℃). No.1a−180 CDCl3+CD3OD 300MHz 1.03−1.86(14H,m),2.08−2.17(3H,m),2.91(1H,
m),5.06−5.10(2H,m),6.76(1H,m),6.86−6.90(2
H,m),7.48(1H,m),7.61−7.69(3H,m),7.89(1H,
m). IR(CHCl3):3360,3259,2954,2873,1706,1612,1497,145
7,1360,1306,1272,1230,1176,1148,1126/cm. [α]D=+20.3゜(CH3OH,C=1.00,22℃). No.1a−181 CDCl3 300MHz 0.97−1.96(14H,m),2.15(1H,m),2.29(2H,t,J=6.9
Hz),3.05(1H,m),3.81(3H,s),5.08(1H,d,J=6.9H
z),5.23−5.25(2H,m),6.62(1H,s),7.47−7.54(5
H,m),7.59(1H,m),7.70(1H,m),7.97(1H,m). IR(CHCl3):3380,3260,3020,2946,2868,1708,1466,138
8,1328,1149/cm. [α]D=+32.9゜(CHCl3,c=1.07,22℃). No.1a−182 CDCl3 300MHz 0.94−1.90(14H,m),2.25(2H,t,J=7.5Hz),2.30(1
H,m),2.98(1H,m),3.70(3H,s),4.83(1H,d,J=6.6H
z),5.13−5.16(2H,m),6.95(1H,d,J=1.5Hz),7.11
−7.23(2H,m),7.43(1H,d,J=8.1Hz),7.65(1H,d,J
=8.1Hz),7.79−7.93(4H,m),9.08(1H,br). IR(CHCl3):3458,3372,3020,3002,2946,2868,1719,159
8,1452,1422,1321,1300,1157/cm. [α]D=−6.6゜(CHCl3,c=1.00),mp150−151℃ No.1a−183 CDCl3 300MHz 0.95−1.94(14H,m),2.26(1H,m),2.28(2H,t,J=7.5
Hz),3.00(1H,m),5.16−5.19(2H,m),5.32(1H,d,J
=7.2Hz),6.93(1H,d,J=1.2Hz),7.13(1H,m),7.22
(1H,dd,J=7.8,6.6Hz),7.42(1H,d,J=7.8Hz)7.63
(1H,d,J=7.8Hz),7.76(2H,d,J=8.4Hz),7.90(2H,
d,J=8.4Hz),8.95(1H,br). IR(CHCl3):3458,3374,3260,3020,3002,2948,2868,170
8,1598,1452,1422,1301,1156/cm. [α]D=+17.9゜(CHCl3,c=1.01,22℃). No.1a−184 CDCl3 200MHz 0.92−2.00(14H,m),2.20(1H,m),2.34(2H,t,J=6.8
Hz),3.05(1H,m),5.20−5.36(3H,m),7.39−7.44(2
H,m),7.61−7.66(1H,m),7.80−7.84(1H,m),8.05
(2H,d,J=8.6Hz),8.40(2H,d,J=8.6Hz). IR(CHCl3):3384,3271,3019,2958,1709,1615,1599,155
1,1453,1405,1344,1326,1243,1163/cm. [α]D=+18.5゜(CHCl3,C=1.00,21℃). No.1a−185 CDCl3 300MHz 0.89−2.20(15H,m),2.26(2H,d.t,J=2.1and7.2Hz),
2.99(1H,m),5.08(1H,d,J=6.3Hz),5.09−5.24(2H,
m),6.90(1H,d,J=1.2Hz),7.32−7.48(4H,m),7.64
−7.72(3H,m),8.20(1H,d,J=1.2Hz),9.00(1H,
s). IR(CHCl3):3464,3375,3275,3022,2956,1707,1605,149
0,1449,1356,1322,1219,1147,1131/cm. [α]D=+21.6゜(CHCl3,C=1.01,23℃). No.1a−186 CDCl3 300MHz 1.36−2.24(14H,m),2.31(2H,t,J=7.4Hz),2.49(1
H,bs),3.37(1H,m),3.67(3H,s),5.38−5.50(2H,
m),7.40−7.68(9H,m). IR(CHCl3):3375,1727,1602,1435,1362,1221,1207,116
8,1045/cm. No.1a−187 CDCl3 300MHz 1.10−2.25(14H,m),2.36(2H,t,J=7.2Hz),2.47(1
H,m),3.37(1H,m),5.35−5.54(2H,m),5.62(1H,d,J
=7.2Hz),7.39−7.70(9H,m). IR(CHCl3):3674,3496,3376,3234,3012,2952,2880,265
0,1725(sh),1709,1602,1485,1420,1360,1167/cm. [α]D=+32゜(CHCl3,c=1.69). No.1a−188 CDCl3 200MHz 0.86−1.92(14H,m),2.22(3H,m),2.36(3H,s),2.95
(1H,m),3.67(3H,s),3.93(3H,s),4.81(1H,d,J=
6.2Hz),5.04−5.20(2H,m),7.02−7.05(2H,m),7.31
(1H,d,J=8.6Hz),7.39(1H,d,J=7.8Hz),7.79−7.89
(3H,m). IR(CHCl3):3385,3286,3029,3019,3015,2954,2877,171
8,1617,1598,1567,1507,1311,1269,1153/cm. [α]D=−29.4゜(CHCl3,c=1.01,25℃)。
Hz),2.66(3H,s),3.14(1H,m),5.12−5.22(2H,m),
5.41(1H,d,J=7.2Hz),7.45(1H,d.d,J=2.1&8.7H
z),7.76(1H,d,J=8.7Hz),7.78(1H,d,J=2.1Hz). IR(CHCl3):3372,3250,3022,2950,2868,1707,1514,141
9,1336,1279,1154,1112/cm. [α]D=−4.1゜(CHCl3,C=1.08,26.0℃)m.p.141−
143℃ No.1a−173 CDCl3 300MHz 1.15−2.42(17H,m),2.91(1H,m),5.15(1H,d,J=4.2
Hz),5.25−5.40(2H,m),7.85(1H,d,J=7.2Hz),8.00
(1H,d,J=8.1Hz),8.15−8.20(2H,m),8.67(1H,d,J
=8.1Hz),8.73(1H,d,J=8.1Hz),8.83(1H,s),9.43
(1H,s). IR(KBr):3422,3269,3046,2952,2871,1711,1617,1447,
1333,1243,1161,1146/cm. [α]D=−41.0゜(CH30H,C=1.01,23℃). No.1a−174 CDCl3+d6−DMSO 300MHz 1.00−1.92(14H,m),2.20(2H,t,J=6.6Hz),2.35(1
H,m),2.92(1H,m),5.05−5.22(2H,m),6.63(1H,d,J
=5.4Hz),7.77−7.92(3H,m),8.31(1H,d.d,J=1.8an
d8.7Hz),8.59(1H,d,J=8.7Hz),8.73(1H,d,J=8.7H
z),9.01(1H,s),9.55(1H,d,J=1.8Hz). IR(KBr):3433,3252,2952,2871,1696,1578,1423,1335,
1308,1219,1185,1160,1106/cm. [α]D=−19.3゜(DMSO,C=0.50,23℃). No.1a−175 CDCl3 300MHz 0.96−1.87(14H,m),2.20−2.25(3H,m),2.95(1H,
m),3.66(3H,s),4.74(1H,d,J=6.6Hz),5.10−5.12
(2H,m),6.88(1H,d,J=1.2Hz),7.37−7.50(3H,m),
7.56(1H,dd,J=8.7,1.5Hz),7.68−7.77(3H,m),8.06
(1H,s),9.44(1H,dd,J=1.2Hz). IR(CHCl3):3462,3374,3026,3006,2952,2872,1724,161
0,1580,1484,1452,1358,1309,1147. [α]D=+16.4゜(CHCl3,c=1.05,26℃).mp.130−1
32℃. No.1a−176 CDCl3+CD3OD 300MHz 1.00−2.02(14H,m),2.22(1H,m),2.29(2H,t,J=6.9
Hz),2.88(1H,m),5.16−5.26(2H,m),6.87(1H,s),
7.28−7.57(4H,m),7.69(1H,d,J=8.4Hz),7.75−7.7
8(2H,m),7.99(1H,s). IR(KBr):3254,2944,1704,1484,1453,1358,1305,1147. [α]D=+13.0゜(CH3OH,c=1.02,24℃),mp.160−1
61℃ No.1a−177 CDCl3 300MHz 0.96−1.88(14H,m),1.88−2.26(3H,m),2.94(1H,
m),3.67(3H,s),3.87(3H,s),4.67(1H,brs),5.08
−5.14(2H,m),6.77(1H,d,J=1.5Hz),6.99−7.02(2
H,m),7.53−7.57(1H,m),7.65−7.70(3H,m),8.00
(1H,s),9.27(1H,brs). IR(CHCl3):3426,3376,3006,2952,1724,1610,1495,143
8,1357,1308,1282,1249,1177,1147/cm. [α]D=+18.1゜(CHCl3,C=1.02,22℃). No.1a−178 CDCl3+CD3OD 300MHz 0.96−1.91(14H,m),2.19(1H,m),2.27(2H,t,J=6.0
Hz),2.85(1H,m),3.87(3H,s),5.16−5.23(2H,m),
6.99−7.02(2H,m),7.41(1H,m),7.64−7.73(3H,
m),7.92(1H,m). IR(CHCl3):3366,3261,3004,2954,2873,1705,1611,149
6,1458,1438,1304,1286,1253,1180,1149,1128/cm. [α]D=+14.6゜(CHCl3,C=1.02,22℃). No.1a−179 CDCl3+CD3OD 300MHz 0.96−1.87(14H,m),2.15−2.23(3H,m),2.93(1H,
m),3.85(3H,s),5.10−5.16(2H,m),6.90−6.93(2
H,m),7.50(1H,m),7.60−7.65(3H,m),7.91(1H,d,J
=0.9Hz). IR(CHCl3):3369,3270,2950,2873,1719,1612,1498,145
6,1440,1359,1306,1269,1219,1146,1127/cm. [α]D=+18.1゜(CH3OH,C=1.00,22℃). No.1a−180 CDCl3+CD3OD 300MHz 1.03−1.86(14H,m),2.08−2.17(3H,m),2.91(1H,
m),5.06−5.10(2H,m),6.76(1H,m),6.86−6.90(2
H,m),7.48(1H,m),7.61−7.69(3H,m),7.89(1H,
m). IR(CHCl3):3360,3259,2954,2873,1706,1612,1497,145
7,1360,1306,1272,1230,1176,1148,1126/cm. [α]D=+20.3゜(CH3OH,C=1.00,22℃). No.1a−181 CDCl3 300MHz 0.97−1.96(14H,m),2.15(1H,m),2.29(2H,t,J=6.9
Hz),3.05(1H,m),3.81(3H,s),5.08(1H,d,J=6.9H
z),5.23−5.25(2H,m),6.62(1H,s),7.47−7.54(5
H,m),7.59(1H,m),7.70(1H,m),7.97(1H,m). IR(CHCl3):3380,3260,3020,2946,2868,1708,1466,138
8,1328,1149/cm. [α]D=+32.9゜(CHCl3,c=1.07,22℃). No.1a−182 CDCl3 300MHz 0.94−1.90(14H,m),2.25(2H,t,J=7.5Hz),2.30(1
H,m),2.98(1H,m),3.70(3H,s),4.83(1H,d,J=6.6H
z),5.13−5.16(2H,m),6.95(1H,d,J=1.5Hz),7.11
−7.23(2H,m),7.43(1H,d,J=8.1Hz),7.65(1H,d,J
=8.1Hz),7.79−7.93(4H,m),9.08(1H,br). IR(CHCl3):3458,3372,3020,3002,2946,2868,1719,159
8,1452,1422,1321,1300,1157/cm. [α]D=−6.6゜(CHCl3,c=1.00),mp150−151℃ No.1a−183 CDCl3 300MHz 0.95−1.94(14H,m),2.26(1H,m),2.28(2H,t,J=7.5
Hz),3.00(1H,m),5.16−5.19(2H,m),5.32(1H,d,J
=7.2Hz),6.93(1H,d,J=1.2Hz),7.13(1H,m),7.22
(1H,dd,J=7.8,6.6Hz),7.42(1H,d,J=7.8Hz)7.63
(1H,d,J=7.8Hz),7.76(2H,d,J=8.4Hz),7.90(2H,
d,J=8.4Hz),8.95(1H,br). IR(CHCl3):3458,3374,3260,3020,3002,2948,2868,170
8,1598,1452,1422,1301,1156/cm. [α]D=+17.9゜(CHCl3,c=1.01,22℃). No.1a−184 CDCl3 200MHz 0.92−2.00(14H,m),2.20(1H,m),2.34(2H,t,J=6.8
Hz),3.05(1H,m),5.20−5.36(3H,m),7.39−7.44(2
H,m),7.61−7.66(1H,m),7.80−7.84(1H,m),8.05
(2H,d,J=8.6Hz),8.40(2H,d,J=8.6Hz). IR(CHCl3):3384,3271,3019,2958,1709,1615,1599,155
1,1453,1405,1344,1326,1243,1163/cm. [α]D=+18.5゜(CHCl3,C=1.00,21℃). No.1a−185 CDCl3 300MHz 0.89−2.20(15H,m),2.26(2H,d.t,J=2.1and7.2Hz),
2.99(1H,m),5.08(1H,d,J=6.3Hz),5.09−5.24(2H,
m),6.90(1H,d,J=1.2Hz),7.32−7.48(4H,m),7.64
−7.72(3H,m),8.20(1H,d,J=1.2Hz),9.00(1H,
s). IR(CHCl3):3464,3375,3275,3022,2956,1707,1605,149
0,1449,1356,1322,1219,1147,1131/cm. [α]D=+21.6゜(CHCl3,C=1.01,23℃). No.1a−186 CDCl3 300MHz 1.36−2.24(14H,m),2.31(2H,t,J=7.4Hz),2.49(1
H,bs),3.37(1H,m),3.67(3H,s),5.38−5.50(2H,
m),7.40−7.68(9H,m). IR(CHCl3):3375,1727,1602,1435,1362,1221,1207,116
8,1045/cm. No.1a−187 CDCl3 300MHz 1.10−2.25(14H,m),2.36(2H,t,J=7.2Hz),2.47(1
H,m),3.37(1H,m),5.35−5.54(2H,m),5.62(1H,d,J
=7.2Hz),7.39−7.70(9H,m). IR(CHCl3):3674,3496,3376,3234,3012,2952,2880,265
0,1725(sh),1709,1602,1485,1420,1360,1167/cm. [α]D=+32゜(CHCl3,c=1.69). No.1a−188 CDCl3 200MHz 0.86−1.92(14H,m),2.22(3H,m),2.36(3H,s),2.95
(1H,m),3.67(3H,s),3.93(3H,s),4.81(1H,d,J=
6.2Hz),5.04−5.20(2H,m),7.02−7.05(2H,m),7.31
(1H,d,J=8.6Hz),7.39(1H,d,J=7.8Hz),7.79−7.89
(3H,m). IR(CHCl3):3385,3286,3029,3019,3015,2954,2877,171
8,1617,1598,1567,1507,1311,1269,1153/cm. [α]D=−29.4゜(CHCl3,c=1.01,25℃)。
No.1a−189 [α]D=−7.7゜(CHCl3,c=1.00,24℃)。
No.1a−190 [α]D=−17.3゜(CHCl3,c=1.00,24℃)。
No.1a−191 CDCl3 300MHz 0.95−2.20(14H,m),2.30(1H,m),2.36(2H,d,J=6.9
Hz),3.21(1H,m),4.25(2H,s),5.07(1H,d,J=7.8H
z),5.35−5.48(2H,m),7.25(1H,dd,J=1.8and8.1H
z),7.32−7.35(2H,m),7.59(1H,d,J=8.1Hz),7.94
(1H,s),8.14(1H,d,J=2.7Hz),8.23(1H,d.d,J=2.7
and8.7Hz). IR(CHCl3):3386,3026,3015,2957,2877,2633,1702,161
7,1573,1530,1348,1123/cm. [α]D=−6.1゜(CHCl3,c=1.01,25℃)。
Hz),3.21(1H,m),4.25(2H,s),5.07(1H,d,J=7.8H
z),5.35−5.48(2H,m),7.25(1H,dd,J=1.8and8.1H
z),7.32−7.35(2H,m),7.59(1H,d,J=8.1Hz),7.94
(1H,s),8.14(1H,d,J=2.7Hz),8.23(1H,d.d,J=2.7
and8.7Hz). IR(CHCl3):3386,3026,3015,2957,2877,2633,1702,161
7,1573,1530,1348,1123/cm. [α]D=−6.1゜(CHCl3,c=1.01,25℃)。
No.1a−192 CDCl3 300MHz 0.92−2.20(14H,m),2.13(3H,m),3.23(1H,m),3.64
(3H,s),3.94(3H,s),4.22(2H,s),4.36(1H,d,J=
7.8Hz),5.37−5.42(2H,m),7.16−7.42(6H,m),7.53
(1H,d,J=8.4Hz),7.94(1H,s). IR(CHCl3):3389,3022,3013,2953,2877,1716,1616,156
0,1485,1340,1326,1124/cm. [α]D=−15.2゜(CHCl3,c=1.01,25℃)。
(3H,s),3.94(3H,s),4.22(2H,s),4.36(1H,d,J=
7.8Hz),5.37−5.42(2H,m),7.16−7.42(6H,m),7.53
(1H,d,J=8.4Hz),7.94(1H,s). IR(CHCl3):3389,3022,3013,2953,2877,1716,1616,156
0,1485,1340,1326,1124/cm. [α]D=−15.2゜(CHCl3,c=1.01,25℃)。
No.1a−193 CDCl3 300MHz 0.92−2.20(14H,m),2.25(1H,m),2.35(2H,t,J=7.2
Hz),3.17(1H,m),4.22(2H,s),4.91(1H,d,J=7.5H
z),5.37−5.42(2H,m),7.13−7.43(6H,m),7.60(1
H,d,J=8.1Hz),8.05(1H,s). IR(CHCl3):3511,3387,3029,3020,3011,2957,2877,265
1,1698,1614,1560,1505,1320,1280,1252,1126/cm. [α]D=−0.9゜(CHCl3,c=1.0,25℃)。
Hz),3.17(1H,m),4.22(2H,s),4.91(1H,d,J=7.5H
z),5.37−5.42(2H,m),7.13−7.43(6H,m),7.60(1
H,d,J=8.1Hz),8.05(1H,s). IR(CHCl3):3511,3387,3029,3020,3011,2957,2877,265
1,1698,1614,1560,1505,1320,1280,1252,1126/cm. [α]D=−0.9゜(CHCl3,c=1.0,25℃)。
No.1b−1 CDCl3 300MHz 0.98−1.56(15H,m),1.85−1.90(5H,m),2.23(1H,
m),3.05(1H,m),3.66(3H,s),4.77(1H,d,J=6.0H
z),5.08−5.28(2H,m),7.46(3H,m),7.38−7.54(2
H,d,J=7.5Hz),7.72(2H,d,J=8.4Hz),7.93(2H,d,J
=8.4Hz). IR(CHCl3):3384,3028,2952,2876,1719,1595,1391,132
2,1155/cm. [α]436+4.0〜+6.0(CHCl3,c=1.00,23℃). mp.96−98℃ No.1b−2 CDCl3 300MHz 0.98−1.52(15H,m),1.85−1.90(5H,m),2.17(1H,
m),3.00(1H,m),3.67(3H,s),4.05(2H,s),4.83(1
H,d,J=6.0Hz),5.05−5.23(2H,m),7.14(2H,d,J=7.
2Hz),7.17−7.32(5H,m),7.78(2H,d,J=8.4Hz). IR(CHCl3):3384,3026,2952,2874,1719,1595,1453,140
7,1320,1180/cm. [α]D=+2.5゜(CHCl3,c=1.02,24℃). No.1b−3 CDCl3 300MHz 0.96−2.05(20H,m),2.07(1H,m),3.07(1H,m),4.04
(2H,s),5.21−5.35(2H,m),5.55(1H,d,J=6.9Hz),
7.14(2H,d,J=6.6Hz),7.20−7.32(5H,m),7.78(2H,
d,J=8.1Hz). IR(CHCl3):3250,3022,2950,1699,1596,1495,1453,140
5,1318,1153/cm. [α]D=+17.1゜(CHCl3,c=1.01,25℃). mp.129−131℃. No.1b−4 CDCl3 200MHz 0.90−2.10(15H,m),1.19(3H,s),1.20(3H,s),3.11
(1H,m),5.24−5.32(2H,m),5.70(1H,d,J=6.6Hz),
7.38−7.68(4H,m),7.96−8.04(2H,m),8.53(1H,d,J
=1.4Hz). IR(CHCl3):3384,3246,2958,1701,1632,1595,1468,144
5,1322,1216,1202,1190,1155,1122/cm. [α]D=+10.8゜(CHCl3,C=0.51,23℃). No.1b−5 1.02−2.10(15H,m),1.16(6H,s),3.02(1H,m),4.09
(3H,s),5.23−5.28(2H,m),5.76(1H,d,J=7.2Hz),
7.36−7.63(4H,m),7.97(1H,d,J=7.8Hz),8.16(1H,
s). IR(CHCl3):3369,2959,1702,1635,1585,1468,1454,144
1,1415,1318,1222,1189,1170,1154/cm. [α]D=+9.9゜(CHCl3,C=1.00,23℃). No.1c−1 CDCl3 300MHz 1.10−2.02(14H,m),2.27(2H,t,J=7.5Hz),2.50(1
H,m),2.89(3H,s),3.31(1H,m),3.64(3H,s),5.16
−5.30(2H,m),7.34−7.42(3H,m),7.50−7.59(2H,
m),7.62−7.68(2H,m),7.76−7.82(2H,m). IR(CHCl3):3020,2946,2868,2212,1727,1596,1495,143
7,1339,1156,1135,1084/cm. [α]D=−16.1゜(CHCl3,c=1.05,25.0℃). m.p.100−102℃ No.1c−2 CDCl3 300MHz 1.10−2.05(14H,m),2.23(2H,t,J=7.5Hz),2.53(1
H,m),2.91(3H,s),3.35(1H,m),3.62(3H,s),5.02
−5.30(2H,m),7.50−7.60(3H,m),7.90−8.08(6H,
m). IR(CHCl3):3016,2946,2868,1728,1437,1398,1340,116
0,1086/cm. [α]D=−32.5゜(CHCl3,c=1.00,25.0℃). No.1c−3 CD3OD 300MHz 1.15−2.05(14H,m),2.13(2H,t,J=7.2Hz),2.47(1
H,m),2.91(3H,s),3.27(1H,m),4.90−5.30(2H,
m),7.37−7.44(3H,m),7.53−7.61(2H,m),7.71−7.
77(2H,m),7.81−7.87(2H,m). IR(KBr):3412,2999,2951,2871,2217,1560,1399,1243,
1159,1137,1103,1084. [α]D=−8.6゜(CH3OH,c=1.03,23℃). No.1d−1 CDCl3 300MHz 1.00−2.16(15H,m),2.36(2H,t,J=7.2Hz),3.17(1
H,m),3.33(3H,s),5.23−5.43(3H,m),7.51−7.59
(3H,m),7.91−8.10(6H,m),9.02(1H,brs). IR(CHCl3):3382,3268,3028,2954,2874,1715,1442,140
0,1337,1162,1120,1089/cm. [α]D=+40.0゜(CHCl3,c=0.53,22℃). No.1d−2 CDCl3 300MHz 1.03−2.30(17H,m),3.03(1H,m),4.03(2H,s),5.26
(2H,m),5.84(1H,br),5.25−5.29(1H,d,J=6.6H
z),6.03(1H,br),7.14(2H,d,J=8.1Hz),7.26−7.31
(5H,m),7.80(2H,d,J=8.1Hz). IR(CHCl3):3376,3002,2946,1669,1595,1492,1454,140
6,1318,1154/cm. [α]D=+4.3゜(CHCl3,c=1.00,23℃). No.1d−3 CDCl3 300MHz 0.96−2.17(17H,m),2.33(2H,t,J=6.9Hz),3.01(1
H,m),4.04(2H,s),5.10(1H,d,J=6.6Hz),5.21−5.2
6(2H,m),7.14(2H,d,J=8.7Hz),7.16−7.32(5H,
m),7.78(2H,d,J=8.4Hz). IR(CHCl3):3260,3020,2946,1711,1596,1492,1457,140
7,1318,1154/cm. [α]D=+9.3゜(CHCl3,c=1.09,25℃). No.1d−4 CDCl3 300MHz 0.95−2.14(15H,m),2.34(2H,t,J=7.2Hz),3.09(1
H,m),3.30(3H,s),4.04(2H,s),5.19(1H,d,J=7.2H
z),5.22−5.39(2H,m),7.10−7.35(7H,m),7.81(2
H,d,J=8.1Hz),9.10(1H,brs). IR(CHCl3):3382,3260,3028,2952,2874,2670,1713,159
5,1492,1450,1405,1338,1160,1120,1092/cm. [α]D=+22.2゜(CHCl3,C=1.07,22℃). No.1d−5 CDCl3 300MHz 1.00−2.10(14H,m),2.30−2.39(3H,m),3.15(1H,
m),3.35(3H,s),5.18−5.40(3H,m),7.41(1H,d.t.,
J=0.9and7.8Hz),7.50−7.69(3H,m),7.88−8.15(2
H,m),8.60(1H,d,J=1.5Hz),9.06(1H,s). IR(CHCl3):3382,3268,3028,2954,2874,1714,1442,140
2,1338,1188,1155,1121,1072/cm. [α]D=+15.3゜(CHCl3,C=1.00,22℃). No.1e−1 CDCl3 300MHz 1.19−2.45(19H,m),2.58(1H,m),5.63(1H,d,J=3.0
Hz),7.42−7.65(4H,m),7.94−8.03(2H,m),8.49−
8.50(1H,m). IR(CHCl3):3293,3024,1710,1595,1584,1467,1445,141
0,1324,1222,1213,1206,1190,1160/cm. [α]D=−41.1゜(CHCl3,C=1.01,23℃). No.1e−2 CDCl3 300MHz 1.10−2.25(19H,m),2.94(1H,m),4.12(3H,s),5.53
(1H,d,J=7.2Hz),7.39(1H,m),7.50−7.62(3H,m),
7.96(1H,d,J=7.5Hz),8.13(1H,s). IR(CHCl3):3367,3025,2955,1711,1634,1600,1584,146
8,1454,1440,1415,1342,1317,1222,1189,1157/cm. [α]D=+1.2゜(CHCl3,C=1.00,25℃). No.1f−1 CDCl3 300MHz 1.08−2.47(19H,m),2.56(1H,m),3.52(2H,t,J=6.6
Hz),5.59(1H,d,J=2.4Hz),7.40−7.64(4H,m),7.95
−8.04(2H,m),8.50(1H,d,J=1.8Hz). IR(CHCl3):3624,3383,3295,2950,2877,1705,1595,158
4,1468,1445,1405,1347,1337,1324,1224,1190,1160/cm. [α]D=−54.1゜(CHCl3,C=1.01,23℃). No.1f−2 CDCl3 300MHz 1.08−2.24(19H,m),2.94(1H,m),3.53(2H,t,J=6.3
Hz),4.13(3H,s),5.47(1H,d,J=6.6Hz),7.36−7.63
(4H,m),7.96(1H,d,J=6.3Hz),8.14(1H,s). IR(CHCl3):3625,3368,3025,3013,2949,2877,1710,163
4,1600,1584,1468,1454,1440,1415,1342,1317,1232,122
0,1189,1157/cm. [α]D=−5.6゜(CHCl3,C=1.00,25℃). No.1g−1 CDCl3 200MHz 1.17−2.34(15H,m),3.22(1H,m),5.10−5.16(2H,
m),5.45(1H,d,J=7.0Hz),7.35−7.66(4H,m),7.95
−8.01(2H,m),8.51(1H,d,J=2.0Hz). IR(CHCl3):3383,3275,2959,1707,1595,1584,1468,144
5,1425,1319,1269,1248,1190,1149,1123/cm. [α]D=+64.3゜(CHCl3,C=1.01,23℃). No.1g−2 CDCl3 300MHz 1.10−2.15(13H,m),2.36(2H,t,J=7.2Hz),3.21(1
H,m),4.09(3H,s),5.10−5.22(2H,m),5.43(1H,d,J
=7.8Hz),7.36−7.62(4H,m),7.96(1H,d,J=7.8H
z),8.12(1H,s). IR(CHCl3):3366,2959,1708,1635,1600,1585,1467,145
4,1440,1415,1345,1318,1233,1189,1152/cm. [α]D=+103.1゜(CHCl3,C=1.01,23℃). No.1h−1 CDCl3 300MHz 0.90−1.60(17H,m),1.83(1H,m),2.11(1H,m),2.22
(2H,t,J=7.2Hz),3.07(1H,m),5.11(1H,d,J=7.2H
z),7.38−7.47(1H,m),7.50−7.60(1H,m),7.60−7.
72(2H,m),7.88−8.12(2H,m),8.54(1H,d,J=0.9H
z). IR(CHCl3):3382,3274,2926,1707,1464,1442,1318,126
6,1188,1153,1121,1105,1071,1019/cm. [α]D=−2.8゜(CHCl3,C=1.01,23℃). No.1i−1 [α]365+50.9゜(CHCl3,c=1.01,24℃). No.1i−2 CDCl3 300MHz 0.98−1.70(11H,m),1.80−2.00(5H,m),2.19(1H,
m),3.03(1H,m),3.64(2H,t,J=6.6Hz),4.05(2H,
s),4.69(1H,d,J=6.6Hz),5.15(1H,m),5.25(1H,
m),7.16(2H,d,J=7.2Hz),7.27−7.32(5H,m),7.77
(2H,d,J=8.4Hz). IR(CHCl3):3376,3004,2946,2316,1596,1492,1453,140
7,1318,1154/cm. [α]D=+3.5゜(CHCl3,c=1.00,22℃). mp.80.5−82.0℃ No.1j−1 [α]436=−7.5±0.5゜(CHCl3,c=1.05,22℃). No.1j−2 [α]D==−9.7±0.5゜(CHCl3,c=1.06,22℃). No.1j−3 [α]D==+15.0±0.5゜(CH3OH,c=1.06,24.5
℃). mp.101−108℃ No.1j−4 [α]D==−28.0±0.6゜(CHCl3,c=1.06,24℃). mp.159−161℃ 1j−5 [α]D==−12.5±0.5゜(CHCl3,c=1.04,23℃). mp.99−101℃ No.1j−6 CDCl3 300MHz 0.90−2.03(14H,m),2.20(1H,m),2.30(2H,t,J=7.3
Hz),3.00(1H,m),3.68(3H,s),4.76(1H,d,J=6.8H
z),5.13−5.35(2H,m),7.01−7.08(4H,m),7.19−7.
26(1H,m),7.37−7.46(2H,m),7.80−7.84(2H,m). IR(CHCl3):3382,3280,3080,3016,2952,2900,1727,158
2,1486,1432,1322,1150/cm. [α]D=−31.0゜(CHCl3,c=1.05,26℃). No.1j−7 CDCl3 300MHz 0.91−2.09(14H,m),2.15(1H,m),2.35(2H,t,J=7.5
Hz),3.01(1H,m),5.17(1H,d,J=6.8Hz),5.21−5.34
(2H,m),7.01−7.08(4H,m),7.15−7.27(1H,m),7.3
7−7.43(2H,m),7.80−7.85(2H,m). IR(CHCl3):3474,3386,3270,3024,2958,2900,2675,171
1,1584,1488,1420,1323,1298,1150/cm. [α]D=−13.4゜(CHCl3,c=1.01,26℃). No.1j−8 CDCl3 300MHz 0.95−2.14(13H,m),2.30(2H,t,J=7.5Hz),2.36(1
H,m),2.84(1H,m),2.91(1J=4.8Hz),3.66(3H,s),
5.33−5.52(2H,m),6.82−6.87(1H,m),6.93−7.00
(2H,m),7.09−7.15(4H,m),7.28−7.36(2H,m),7.5
4−7.59(1H,m). IR(CHCl3):3350,3010,2950,2880,1728,1603,1582,148
9 1461,1438,1360,1160/cm. [α]D=+75.1゜(CHCl3,c=1.13,26℃). No.1j−9 CDCl3 300MHz 0.95−2.03(14H,m),2.20(1H,m),2.29(2H,t,J=7.5
Hz),3.06(1H,m),3.68(3H,s),4.98(1H,d,J=7.4H
z),5.14−5.34(2H,m),7.46−7.54(2H,m),7.60−7.
68(1H,m),7.75−7.80(2H,m),7.88−7.92(2H,m),
7.99−8.03(2H,m). IR(CHCl3):3384,3280,3020,2960,2888,1727,1662,160
0,1316,1273,1163/cm. [α]D=−41.0゜(CHCl3,c=1.17,26℃). No.1j−10 CDCl3+CD3OD 300MHz 0.94−2.08(14H,m),2.21(1H,m),2.34(2H,t,J=6.2
Hz),3.04(1H,m),5.21−5.35(2H,m),5.40(1H,m),
7.49−7.58(2H,m),7.64−7.68(1H,m),7.79−8.06
(6H,m). IR(CHCl3):3475,3370,3250,3018,2956,2976,2650,170
9,1662,1595,1445,1420,1395,1317,1274,1163/cm. [α]D=−17.1゜(CHCl3,c=1.13,25℃). No.1J−11 CDCl3 300MHz 1.06−1.98(14H,m),2.24−2.29(3H,m),3.13(1H,
m),3.66(3H,s),5.10−5.24(2H,m),5.40(1H,d,J=
6.3Hz),7.39−7.49(3H,m),7.59−7.64(3H,m),7.80
−7.83(2H,m),8.08−8.11(1H,m). IR(CHCl3):3302,3012,2948,2905,1727,1661,1593,143
5,1332,1312,1287,1271,1165/cm. [α]D=+15.6゜(CHCl3,c=1.03,26℃). No.1j−12 CDCl3 300MHz 1.08−1.98(14H,m),2.23(1H,m),2.33(2H,t,J=7.5
Hz),3.16(1H,m),5.18−5.26(2H,m),5.39−5.45(1
H,m),7.39−7.49(3H,m),7.60−7.64(3H,m),7.80−
7.83(2H,m),8.09−8.12(1H,m). IR(CHCl3):3325,3022,2956,2872,2680,1708,1662,160
3,1598,1425,1340,1316,1288,1271,1165/cm. [α]D=+9.7゜(CHCl3,c=0.52,25℃). No.1j−13 CDCl3 300MHz 0.95−2.00(14H,m),2.20(1H,m),2.27(2H,t,J=6.3
Hz),3.03(1H,m),3.67(3H,s),4.99(1H,d,J=6.6H
z),5.12−5.31(2H,m),7.47−7.55(2H,m),7.60−7.
69(2H,m),7.76−7.81(2H,m),7.96−8.05(1H,m),
8.08−8.14(1H,m),8.27−8.28(1H,m). IR(CHCl3):3674,3538,3376,3276,3012,2948,2860,172
6,1662,1595,1440,1335,1317,1297,1274,1166,1150/cm. [α]D=+10.2゜(CHCl3,c=1.00,25℃). No.1j−14 CDCl3 300MHz 0.93−2.08(14H,m),2.21(1H,m),2.32(2H,t,J=6.3
Hz),3.00(1H,m),5.20−5.36(2H,m),5.38(1H,d,J
=6.2Hz),7.50−7.55(2H,m),7.63−7.71(2H,m),7.
77−7.81(2H,m),7.99−8.04(1H,m),8.10−8.18(1
H,m),8.32−8.36(1H,m). IR(CHCl3):3674,3480,3374,3258,3012,2950,2875,265
0,1709,1662,1598,1418,1335,1317,1274,1143/cm. [α]D=+61.0゜(CHCl3,c=1.19,25℃). No.1j−15 CDCl3 300MHz 0.90−2.00(14H,m),2.19(1H,m),2.30(2H,t,J=7.3
Hz),3.01(1H,m),3.67(3H,s),4.82(1H,d,J=6.6H
z),5.14−5.34(2H,m),7.36−7.39(3H,m),7.53−7.
57(2H,m),7.62−7.66(2H,m),7.83−7.88(2H,m). IR(CHCl3):3376,3276,3010,2948,2868,2212,1727,159
7,1500,1437,1325,1161/cm. [α]D=−7.2゜(CHCl3,c=1.00,26℃). No.1j−16 CDCl3 300MHz 0.93−2.03(14H,m),2.15(1H,m),2.36(2H,t,J=7.5
5Hz),3.05(1H,m),5.20−5.40(3H,m),7.36−7.39
(3H,m),7.55−7.66(4H,m),7.84−7.88(2H,m). IR(CHCl3):3470,3376,3260,3012,2950,2868,2675,221
2,1708,1596,1503,1416,1396,1322,1160. [α]D=−22.4゜(CHCl3,c=1.00,26℃). No.1j−17 CDCl3 300MHz 1.00−1.60(9H,m),1.79−1.89(5H,m),2.17(1H,b
s),2.23(2H,t,J=7.2Hz),3.03(1H,m),5.10−5.23
(2H,m),5.49(1H,d,J=6.6Hz),7.40(1H,t,J=7.4H
z),7.53(1H,t,J=7.2Hz),7.60−7.68(2H,m),7.98
−8.03(2H,m),8.55(1H,d,J=1.5Hz). IR(CHCl3):3516,3384,3270,2666,1708,1632,1595,158
4,1467,1445,1425,1374,1345,1321,1269,1248,1218/cm. [α]D=−7.8゜(CHCl3,c=1.01,22℃). No.1j−18 CDCl3 300MHz 0.90−2.03(14H,m),2.19(1H,m),2.30(2H,t,J=7.5
Hz),3.00(1H,m),3.67(3H,s),4.80(1H,d,J=6.4H
z),5.14−5.35(2H,m),6.99−7.04(2H,m),7.16−7.
22(2H,m),7.34−7.49(4H,m),7.57−7.61(1H,m). IR(CHCl3):3376,3276,3012,2948,2875,1727,1583,148
8,1471,1432,1330,1311,1150/cm. [α]D=+54.0゜(CHCl3,c=0.99,25℃). No.1j−19 CDCl3 300MHz 0.91−2.09(14H,m),2.15(1H,m),2.34(2H,t,J=7.5
Hz),3.01(1H,m),5.16(1H,d,J=6.6Hz),5.24−5.40
(2H,m),7.01−7.08(2H,m),7.15−7.25(2H,m),7.3
5−7.53(4H,m),7.59−7.65(1H,m). IR(CHCl3):3470,3376,3260,3012,2950,2875,2640,170
8,1583,1488,1471,1430,1335,1305,1149/cm. [α]D=−21.0゜(CHCl3,c=1.30,25℃). No.1j−20 CDCl3 300MHz 1.17(1H,m),1.26−1.34(2H,m),1.54−2.24(11H,
m),2.31(2H,t,J=7.4Hz),2.48(1H,bs),3.37(1H,
m),3.67(3H,s),5.35−5.50(2H,m),7.39−7.68(9
H,m). IR(CHCl3):3377,1727,1601,1435,1362,1168/cm. No.1j−21 CDCl3 300MHz 1,10−2.25(14H,m),2.36(2H,t,J=7.2Hz),2.47(1
H,m),2.89(1H,m),5.35−5.53(2H,m),5.63(1H,d,J
=7.2Hz),7.40−7.71(9H,m). IR(CHCl3):3674,3496,3374,3234,3010,2952,2870,264
0,1730(sh),1710,1605,1485,1425,1360,1167/cm. [α]D=−43.0゜(CHCl3,c=1.01,25℃). No.1j−22 CDCl3 300MHz 0,98−1.95(14H,m),2.25−2,31(3H,m),2.95(1H,
m),5.19−5.30(2H,m),5.33(1H,d,J=3.9Hz),6.58
(1H,d,J=7.5Hz),6.80(1H,t,J=7.5Hz),6.99−7.05
(1H,m),7.44−7.53(6H,m),7.60−7.73(9H,m),7.9
4−7.73(3H,m),8.23−8.26(2H,m),10.66(1H,s). IR(CHCl3):3475,3372,3260,3008,2952,2868,2722,172
5,1710(sh),1663,1590,1571,1525,1448,1437,1345,13
14,1161,1112/cm. [α]D=+12.9゜(CHCl3,c=0.12,23℃). No.1j−23 CDCl3 300MHz 0.94〜1.94(14H,m),2.23−2.30(3H,m),2.98(1H,
m),3.68(3H,s),5.09(1H,d,J=6.2Hz),5.15−5.28
(2H,m),7.14−7.22(1H,m),7.34−7.42(2H,m),7.6
8−7.73(2H,m),7.89−8.03(4H,m),8.51(1H,s). IR(CHCl3):3372,3275,1724,1673,1599,1438,1320,116
1/cm. [α]D=+17.0゜(CHCl3,c=1.38,25℃). No.1j−24 CDCl3+CD3OD 300MHz 0.96−2.05(14H,m),2,25−2.34(3H,m),2.92(1H,
m),5.16−5.34(2H,m),7.14−7.22(1H,m),7.29−7.
42(2H,m),7.70(2H,d,J=7.6Hz),7.92−8.05(4H,
m). IR(CHCl3):3616,3426,3375,3010,2950,2828,2645,170
8,1672,1599,1439,1323,1161/cm. [α]D=+21.0゜(CH3OH,c=1.00,22℃). No.1j−25 CDCl3 300MHz 1.03(1H,m),1.18−2.01(13H,m),2.20(1H,bs),2.2
7(2H,t,J=7.4Hz),3.08(1H,m),3.66(3H,s),5.11
(1H,d,J=6.6Hz),5.14−5.34(2H,m),7.54−7.62(3
H,m),8.04−8.32(6H,m). IR(CHCl3):3384,3278,1726,1605,1484,1448,1331,116
1/cm. No.1j−26 CDCl3+CD3OD 300MHz 1,03−2.10(14H,m),2.22(1H,m),2.31(2H,t,J=7.5
Hz),2.98(1H,m),5.23−5.38(2H,m),7.55−7.66(3
H,m),8.05−8.08(2H,m),8.14−8.18(2H,m),8.28−
8.31(2H,m). IR(Nujol):3260,2720,2660,1711,1545,1460,1317,116
3/cm. [α]D=+15.8゜(CH3OH,c=1.01,22℃). No.1j−27 [α]D=+16.7゜(CHCl3,c=1.00,23℃). No.1j−28 CDCl3 300MHz 1.01(1H,m),1.14−1.29(2H,m),1.46−2.19(11H,
m),2.33(2H,t,J=7.2Hz),2.41(1H,bs),3.18−3.21
(5H,m),3.68(3H,s),3.73−3.76(4H,m),4.37(1H,
d,J=7.2Hz),5.35−5.45(2H,m). IR(CHCl3):3392,1727,1435,1335,1148/cm. [α]D=+10.7゜(CHCl3,c=1.39,26℃). No.1j−29 CDCl3 300MHz 1.00(1H,m),1.20−1.29(2H,m),1,48−2.25(12H,
m),2.37(2H,t,J=7.2Hz),3.17−3.22(5H,m),3.74
−3.79(4H,m),4.79(1H,d,J=7.8Hz),5.34−5.54(2
H,m). IR(CHCl3):3470,3390,3270,2675,1709,1455,1420,131
5,1147/cm. [α]D=+16.8゜(CHCl3,c=1.42,26℃). No.1k−1 [α]D=−25.4゜(CHCl3,c=1.08,23℃). No.1k−2 CDCl3 200MHz 1.07−2.28(14H,m),2.32(2H,t,J=7.4Hz),2.63(1
H,m),3.63(3H,s),3.93(1H,m),5.30−5.52(2H,
m),6.35(1H,d,J=7.0Hz),7.48−7.60(3H,m),7.88
−8.02(6H,m). IR(CHCl3):3438,3002,2946,2868,1727,1652,1514,148
5,1363,1310,1245,1154/cm. [α]D==−80.4゜(CHCl3,c=1.01,24.0℃)。
m),3.05(1H,m),3.66(3H,s),4.77(1H,d,J=6.0H
z),5.08−5.28(2H,m),7.46(3H,m),7.38−7.54(2
H,d,J=7.5Hz),7.72(2H,d,J=8.4Hz),7.93(2H,d,J
=8.4Hz). IR(CHCl3):3384,3028,2952,2876,1719,1595,1391,132
2,1155/cm. [α]436+4.0〜+6.0(CHCl3,c=1.00,23℃). mp.96−98℃ No.1b−2 CDCl3 300MHz 0.98−1.52(15H,m),1.85−1.90(5H,m),2.17(1H,
m),3.00(1H,m),3.67(3H,s),4.05(2H,s),4.83(1
H,d,J=6.0Hz),5.05−5.23(2H,m),7.14(2H,d,J=7.
2Hz),7.17−7.32(5H,m),7.78(2H,d,J=8.4Hz). IR(CHCl3):3384,3026,2952,2874,1719,1595,1453,140
7,1320,1180/cm. [α]D=+2.5゜(CHCl3,c=1.02,24℃). No.1b−3 CDCl3 300MHz 0.96−2.05(20H,m),2.07(1H,m),3.07(1H,m),4.04
(2H,s),5.21−5.35(2H,m),5.55(1H,d,J=6.9Hz),
7.14(2H,d,J=6.6Hz),7.20−7.32(5H,m),7.78(2H,
d,J=8.1Hz). IR(CHCl3):3250,3022,2950,1699,1596,1495,1453,140
5,1318,1153/cm. [α]D=+17.1゜(CHCl3,c=1.01,25℃). mp.129−131℃. No.1b−4 CDCl3 200MHz 0.90−2.10(15H,m),1.19(3H,s),1.20(3H,s),3.11
(1H,m),5.24−5.32(2H,m),5.70(1H,d,J=6.6Hz),
7.38−7.68(4H,m),7.96−8.04(2H,m),8.53(1H,d,J
=1.4Hz). IR(CHCl3):3384,3246,2958,1701,1632,1595,1468,144
5,1322,1216,1202,1190,1155,1122/cm. [α]D=+10.8゜(CHCl3,C=0.51,23℃). No.1b−5 1.02−2.10(15H,m),1.16(6H,s),3.02(1H,m),4.09
(3H,s),5.23−5.28(2H,m),5.76(1H,d,J=7.2Hz),
7.36−7.63(4H,m),7.97(1H,d,J=7.8Hz),8.16(1H,
s). IR(CHCl3):3369,2959,1702,1635,1585,1468,1454,144
1,1415,1318,1222,1189,1170,1154/cm. [α]D=+9.9゜(CHCl3,C=1.00,23℃). No.1c−1 CDCl3 300MHz 1.10−2.02(14H,m),2.27(2H,t,J=7.5Hz),2.50(1
H,m),2.89(3H,s),3.31(1H,m),3.64(3H,s),5.16
−5.30(2H,m),7.34−7.42(3H,m),7.50−7.59(2H,
m),7.62−7.68(2H,m),7.76−7.82(2H,m). IR(CHCl3):3020,2946,2868,2212,1727,1596,1495,143
7,1339,1156,1135,1084/cm. [α]D=−16.1゜(CHCl3,c=1.05,25.0℃). m.p.100−102℃ No.1c−2 CDCl3 300MHz 1.10−2.05(14H,m),2.23(2H,t,J=7.5Hz),2.53(1
H,m),2.91(3H,s),3.35(1H,m),3.62(3H,s),5.02
−5.30(2H,m),7.50−7.60(3H,m),7.90−8.08(6H,
m). IR(CHCl3):3016,2946,2868,1728,1437,1398,1340,116
0,1086/cm. [α]D=−32.5゜(CHCl3,c=1.00,25.0℃). No.1c−3 CD3OD 300MHz 1.15−2.05(14H,m),2.13(2H,t,J=7.2Hz),2.47(1
H,m),2.91(3H,s),3.27(1H,m),4.90−5.30(2H,
m),7.37−7.44(3H,m),7.53−7.61(2H,m),7.71−7.
77(2H,m),7.81−7.87(2H,m). IR(KBr):3412,2999,2951,2871,2217,1560,1399,1243,
1159,1137,1103,1084. [α]D=−8.6゜(CH3OH,c=1.03,23℃). No.1d−1 CDCl3 300MHz 1.00−2.16(15H,m),2.36(2H,t,J=7.2Hz),3.17(1
H,m),3.33(3H,s),5.23−5.43(3H,m),7.51−7.59
(3H,m),7.91−8.10(6H,m),9.02(1H,brs). IR(CHCl3):3382,3268,3028,2954,2874,1715,1442,140
0,1337,1162,1120,1089/cm. [α]D=+40.0゜(CHCl3,c=0.53,22℃). No.1d−2 CDCl3 300MHz 1.03−2.30(17H,m),3.03(1H,m),4.03(2H,s),5.26
(2H,m),5.84(1H,br),5.25−5.29(1H,d,J=6.6H
z),6.03(1H,br),7.14(2H,d,J=8.1Hz),7.26−7.31
(5H,m),7.80(2H,d,J=8.1Hz). IR(CHCl3):3376,3002,2946,1669,1595,1492,1454,140
6,1318,1154/cm. [α]D=+4.3゜(CHCl3,c=1.00,23℃). No.1d−3 CDCl3 300MHz 0.96−2.17(17H,m),2.33(2H,t,J=6.9Hz),3.01(1
H,m),4.04(2H,s),5.10(1H,d,J=6.6Hz),5.21−5.2
6(2H,m),7.14(2H,d,J=8.7Hz),7.16−7.32(5H,
m),7.78(2H,d,J=8.4Hz). IR(CHCl3):3260,3020,2946,1711,1596,1492,1457,140
7,1318,1154/cm. [α]D=+9.3゜(CHCl3,c=1.09,25℃). No.1d−4 CDCl3 300MHz 0.95−2.14(15H,m),2.34(2H,t,J=7.2Hz),3.09(1
H,m),3.30(3H,s),4.04(2H,s),5.19(1H,d,J=7.2H
z),5.22−5.39(2H,m),7.10−7.35(7H,m),7.81(2
H,d,J=8.1Hz),9.10(1H,brs). IR(CHCl3):3382,3260,3028,2952,2874,2670,1713,159
5,1492,1450,1405,1338,1160,1120,1092/cm. [α]D=+22.2゜(CHCl3,C=1.07,22℃). No.1d−5 CDCl3 300MHz 1.00−2.10(14H,m),2.30−2.39(3H,m),3.15(1H,
m),3.35(3H,s),5.18−5.40(3H,m),7.41(1H,d.t.,
J=0.9and7.8Hz),7.50−7.69(3H,m),7.88−8.15(2
H,m),8.60(1H,d,J=1.5Hz),9.06(1H,s). IR(CHCl3):3382,3268,3028,2954,2874,1714,1442,140
2,1338,1188,1155,1121,1072/cm. [α]D=+15.3゜(CHCl3,C=1.00,22℃). No.1e−1 CDCl3 300MHz 1.19−2.45(19H,m),2.58(1H,m),5.63(1H,d,J=3.0
Hz),7.42−7.65(4H,m),7.94−8.03(2H,m),8.49−
8.50(1H,m). IR(CHCl3):3293,3024,1710,1595,1584,1467,1445,141
0,1324,1222,1213,1206,1190,1160/cm. [α]D=−41.1゜(CHCl3,C=1.01,23℃). No.1e−2 CDCl3 300MHz 1.10−2.25(19H,m),2.94(1H,m),4.12(3H,s),5.53
(1H,d,J=7.2Hz),7.39(1H,m),7.50−7.62(3H,m),
7.96(1H,d,J=7.5Hz),8.13(1H,s). IR(CHCl3):3367,3025,2955,1711,1634,1600,1584,146
8,1454,1440,1415,1342,1317,1222,1189,1157/cm. [α]D=+1.2゜(CHCl3,C=1.00,25℃). No.1f−1 CDCl3 300MHz 1.08−2.47(19H,m),2.56(1H,m),3.52(2H,t,J=6.6
Hz),5.59(1H,d,J=2.4Hz),7.40−7.64(4H,m),7.95
−8.04(2H,m),8.50(1H,d,J=1.8Hz). IR(CHCl3):3624,3383,3295,2950,2877,1705,1595,158
4,1468,1445,1405,1347,1337,1324,1224,1190,1160/cm. [α]D=−54.1゜(CHCl3,C=1.01,23℃). No.1f−2 CDCl3 300MHz 1.08−2.24(19H,m),2.94(1H,m),3.53(2H,t,J=6.3
Hz),4.13(3H,s),5.47(1H,d,J=6.6Hz),7.36−7.63
(4H,m),7.96(1H,d,J=6.3Hz),8.14(1H,s). IR(CHCl3):3625,3368,3025,3013,2949,2877,1710,163
4,1600,1584,1468,1454,1440,1415,1342,1317,1232,122
0,1189,1157/cm. [α]D=−5.6゜(CHCl3,C=1.00,25℃). No.1g−1 CDCl3 200MHz 1.17−2.34(15H,m),3.22(1H,m),5.10−5.16(2H,
m),5.45(1H,d,J=7.0Hz),7.35−7.66(4H,m),7.95
−8.01(2H,m),8.51(1H,d,J=2.0Hz). IR(CHCl3):3383,3275,2959,1707,1595,1584,1468,144
5,1425,1319,1269,1248,1190,1149,1123/cm. [α]D=+64.3゜(CHCl3,C=1.01,23℃). No.1g−2 CDCl3 300MHz 1.10−2.15(13H,m),2.36(2H,t,J=7.2Hz),3.21(1
H,m),4.09(3H,s),5.10−5.22(2H,m),5.43(1H,d,J
=7.8Hz),7.36−7.62(4H,m),7.96(1H,d,J=7.8H
z),8.12(1H,s). IR(CHCl3):3366,2959,1708,1635,1600,1585,1467,145
4,1440,1415,1345,1318,1233,1189,1152/cm. [α]D=+103.1゜(CHCl3,C=1.01,23℃). No.1h−1 CDCl3 300MHz 0.90−1.60(17H,m),1.83(1H,m),2.11(1H,m),2.22
(2H,t,J=7.2Hz),3.07(1H,m),5.11(1H,d,J=7.2H
z),7.38−7.47(1H,m),7.50−7.60(1H,m),7.60−7.
72(2H,m),7.88−8.12(2H,m),8.54(1H,d,J=0.9H
z). IR(CHCl3):3382,3274,2926,1707,1464,1442,1318,126
6,1188,1153,1121,1105,1071,1019/cm. [α]D=−2.8゜(CHCl3,C=1.01,23℃). No.1i−1 [α]365+50.9゜(CHCl3,c=1.01,24℃). No.1i−2 CDCl3 300MHz 0.98−1.70(11H,m),1.80−2.00(5H,m),2.19(1H,
m),3.03(1H,m),3.64(2H,t,J=6.6Hz),4.05(2H,
s),4.69(1H,d,J=6.6Hz),5.15(1H,m),5.25(1H,
m),7.16(2H,d,J=7.2Hz),7.27−7.32(5H,m),7.77
(2H,d,J=8.4Hz). IR(CHCl3):3376,3004,2946,2316,1596,1492,1453,140
7,1318,1154/cm. [α]D=+3.5゜(CHCl3,c=1.00,22℃). mp.80.5−82.0℃ No.1j−1 [α]436=−7.5±0.5゜(CHCl3,c=1.05,22℃). No.1j−2 [α]D==−9.7±0.5゜(CHCl3,c=1.06,22℃). No.1j−3 [α]D==+15.0±0.5゜(CH3OH,c=1.06,24.5
℃). mp.101−108℃ No.1j−4 [α]D==−28.0±0.6゜(CHCl3,c=1.06,24℃). mp.159−161℃ 1j−5 [α]D==−12.5±0.5゜(CHCl3,c=1.04,23℃). mp.99−101℃ No.1j−6 CDCl3 300MHz 0.90−2.03(14H,m),2.20(1H,m),2.30(2H,t,J=7.3
Hz),3.00(1H,m),3.68(3H,s),4.76(1H,d,J=6.8H
z),5.13−5.35(2H,m),7.01−7.08(4H,m),7.19−7.
26(1H,m),7.37−7.46(2H,m),7.80−7.84(2H,m). IR(CHCl3):3382,3280,3080,3016,2952,2900,1727,158
2,1486,1432,1322,1150/cm. [α]D=−31.0゜(CHCl3,c=1.05,26℃). No.1j−7 CDCl3 300MHz 0.91−2.09(14H,m),2.15(1H,m),2.35(2H,t,J=7.5
Hz),3.01(1H,m),5.17(1H,d,J=6.8Hz),5.21−5.34
(2H,m),7.01−7.08(4H,m),7.15−7.27(1H,m),7.3
7−7.43(2H,m),7.80−7.85(2H,m). IR(CHCl3):3474,3386,3270,3024,2958,2900,2675,171
1,1584,1488,1420,1323,1298,1150/cm. [α]D=−13.4゜(CHCl3,c=1.01,26℃). No.1j−8 CDCl3 300MHz 0.95−2.14(13H,m),2.30(2H,t,J=7.5Hz),2.36(1
H,m),2.84(1H,m),2.91(1J=4.8Hz),3.66(3H,s),
5.33−5.52(2H,m),6.82−6.87(1H,m),6.93−7.00
(2H,m),7.09−7.15(4H,m),7.28−7.36(2H,m),7.5
4−7.59(1H,m). IR(CHCl3):3350,3010,2950,2880,1728,1603,1582,148
9 1461,1438,1360,1160/cm. [α]D=+75.1゜(CHCl3,c=1.13,26℃). No.1j−9 CDCl3 300MHz 0.95−2.03(14H,m),2.20(1H,m),2.29(2H,t,J=7.5
Hz),3.06(1H,m),3.68(3H,s),4.98(1H,d,J=7.4H
z),5.14−5.34(2H,m),7.46−7.54(2H,m),7.60−7.
68(1H,m),7.75−7.80(2H,m),7.88−7.92(2H,m),
7.99−8.03(2H,m). IR(CHCl3):3384,3280,3020,2960,2888,1727,1662,160
0,1316,1273,1163/cm. [α]D=−41.0゜(CHCl3,c=1.17,26℃). No.1j−10 CDCl3+CD3OD 300MHz 0.94−2.08(14H,m),2.21(1H,m),2.34(2H,t,J=6.2
Hz),3.04(1H,m),5.21−5.35(2H,m),5.40(1H,m),
7.49−7.58(2H,m),7.64−7.68(1H,m),7.79−8.06
(6H,m). IR(CHCl3):3475,3370,3250,3018,2956,2976,2650,170
9,1662,1595,1445,1420,1395,1317,1274,1163/cm. [α]D=−17.1゜(CHCl3,c=1.13,25℃). No.1J−11 CDCl3 300MHz 1.06−1.98(14H,m),2.24−2.29(3H,m),3.13(1H,
m),3.66(3H,s),5.10−5.24(2H,m),5.40(1H,d,J=
6.3Hz),7.39−7.49(3H,m),7.59−7.64(3H,m),7.80
−7.83(2H,m),8.08−8.11(1H,m). IR(CHCl3):3302,3012,2948,2905,1727,1661,1593,143
5,1332,1312,1287,1271,1165/cm. [α]D=+15.6゜(CHCl3,c=1.03,26℃). No.1j−12 CDCl3 300MHz 1.08−1.98(14H,m),2.23(1H,m),2.33(2H,t,J=7.5
Hz),3.16(1H,m),5.18−5.26(2H,m),5.39−5.45(1
H,m),7.39−7.49(3H,m),7.60−7.64(3H,m),7.80−
7.83(2H,m),8.09−8.12(1H,m). IR(CHCl3):3325,3022,2956,2872,2680,1708,1662,160
3,1598,1425,1340,1316,1288,1271,1165/cm. [α]D=+9.7゜(CHCl3,c=0.52,25℃). No.1j−13 CDCl3 300MHz 0.95−2.00(14H,m),2.20(1H,m),2.27(2H,t,J=6.3
Hz),3.03(1H,m),3.67(3H,s),4.99(1H,d,J=6.6H
z),5.12−5.31(2H,m),7.47−7.55(2H,m),7.60−7.
69(2H,m),7.76−7.81(2H,m),7.96−8.05(1H,m),
8.08−8.14(1H,m),8.27−8.28(1H,m). IR(CHCl3):3674,3538,3376,3276,3012,2948,2860,172
6,1662,1595,1440,1335,1317,1297,1274,1166,1150/cm. [α]D=+10.2゜(CHCl3,c=1.00,25℃). No.1j−14 CDCl3 300MHz 0.93−2.08(14H,m),2.21(1H,m),2.32(2H,t,J=6.3
Hz),3.00(1H,m),5.20−5.36(2H,m),5.38(1H,d,J
=6.2Hz),7.50−7.55(2H,m),7.63−7.71(2H,m),7.
77−7.81(2H,m),7.99−8.04(1H,m),8.10−8.18(1
H,m),8.32−8.36(1H,m). IR(CHCl3):3674,3480,3374,3258,3012,2950,2875,265
0,1709,1662,1598,1418,1335,1317,1274,1143/cm. [α]D=+61.0゜(CHCl3,c=1.19,25℃). No.1j−15 CDCl3 300MHz 0.90−2.00(14H,m),2.19(1H,m),2.30(2H,t,J=7.3
Hz),3.01(1H,m),3.67(3H,s),4.82(1H,d,J=6.6H
z),5.14−5.34(2H,m),7.36−7.39(3H,m),7.53−7.
57(2H,m),7.62−7.66(2H,m),7.83−7.88(2H,m). IR(CHCl3):3376,3276,3010,2948,2868,2212,1727,159
7,1500,1437,1325,1161/cm. [α]D=−7.2゜(CHCl3,c=1.00,26℃). No.1j−16 CDCl3 300MHz 0.93−2.03(14H,m),2.15(1H,m),2.36(2H,t,J=7.5
5Hz),3.05(1H,m),5.20−5.40(3H,m),7.36−7.39
(3H,m),7.55−7.66(4H,m),7.84−7.88(2H,m). IR(CHCl3):3470,3376,3260,3012,2950,2868,2675,221
2,1708,1596,1503,1416,1396,1322,1160. [α]D=−22.4゜(CHCl3,c=1.00,26℃). No.1j−17 CDCl3 300MHz 1.00−1.60(9H,m),1.79−1.89(5H,m),2.17(1H,b
s),2.23(2H,t,J=7.2Hz),3.03(1H,m),5.10−5.23
(2H,m),5.49(1H,d,J=6.6Hz),7.40(1H,t,J=7.4H
z),7.53(1H,t,J=7.2Hz),7.60−7.68(2H,m),7.98
−8.03(2H,m),8.55(1H,d,J=1.5Hz). IR(CHCl3):3516,3384,3270,2666,1708,1632,1595,158
4,1467,1445,1425,1374,1345,1321,1269,1248,1218/cm. [α]D=−7.8゜(CHCl3,c=1.01,22℃). No.1j−18 CDCl3 300MHz 0.90−2.03(14H,m),2.19(1H,m),2.30(2H,t,J=7.5
Hz),3.00(1H,m),3.67(3H,s),4.80(1H,d,J=6.4H
z),5.14−5.35(2H,m),6.99−7.04(2H,m),7.16−7.
22(2H,m),7.34−7.49(4H,m),7.57−7.61(1H,m). IR(CHCl3):3376,3276,3012,2948,2875,1727,1583,148
8,1471,1432,1330,1311,1150/cm. [α]D=+54.0゜(CHCl3,c=0.99,25℃). No.1j−19 CDCl3 300MHz 0.91−2.09(14H,m),2.15(1H,m),2.34(2H,t,J=7.5
Hz),3.01(1H,m),5.16(1H,d,J=6.6Hz),5.24−5.40
(2H,m),7.01−7.08(2H,m),7.15−7.25(2H,m),7.3
5−7.53(4H,m),7.59−7.65(1H,m). IR(CHCl3):3470,3376,3260,3012,2950,2875,2640,170
8,1583,1488,1471,1430,1335,1305,1149/cm. [α]D=−21.0゜(CHCl3,c=1.30,25℃). No.1j−20 CDCl3 300MHz 1.17(1H,m),1.26−1.34(2H,m),1.54−2.24(11H,
m),2.31(2H,t,J=7.4Hz),2.48(1H,bs),3.37(1H,
m),3.67(3H,s),5.35−5.50(2H,m),7.39−7.68(9
H,m). IR(CHCl3):3377,1727,1601,1435,1362,1168/cm. No.1j−21 CDCl3 300MHz 1,10−2.25(14H,m),2.36(2H,t,J=7.2Hz),2.47(1
H,m),2.89(1H,m),5.35−5.53(2H,m),5.63(1H,d,J
=7.2Hz),7.40−7.71(9H,m). IR(CHCl3):3674,3496,3374,3234,3010,2952,2870,264
0,1730(sh),1710,1605,1485,1425,1360,1167/cm. [α]D=−43.0゜(CHCl3,c=1.01,25℃). No.1j−22 CDCl3 300MHz 0,98−1.95(14H,m),2.25−2,31(3H,m),2.95(1H,
m),5.19−5.30(2H,m),5.33(1H,d,J=3.9Hz),6.58
(1H,d,J=7.5Hz),6.80(1H,t,J=7.5Hz),6.99−7.05
(1H,m),7.44−7.53(6H,m),7.60−7.73(9H,m),7.9
4−7.73(3H,m),8.23−8.26(2H,m),10.66(1H,s). IR(CHCl3):3475,3372,3260,3008,2952,2868,2722,172
5,1710(sh),1663,1590,1571,1525,1448,1437,1345,13
14,1161,1112/cm. [α]D=+12.9゜(CHCl3,c=0.12,23℃). No.1j−23 CDCl3 300MHz 0.94〜1.94(14H,m),2.23−2.30(3H,m),2.98(1H,
m),3.68(3H,s),5.09(1H,d,J=6.2Hz),5.15−5.28
(2H,m),7.14−7.22(1H,m),7.34−7.42(2H,m),7.6
8−7.73(2H,m),7.89−8.03(4H,m),8.51(1H,s). IR(CHCl3):3372,3275,1724,1673,1599,1438,1320,116
1/cm. [α]D=+17.0゜(CHCl3,c=1.38,25℃). No.1j−24 CDCl3+CD3OD 300MHz 0.96−2.05(14H,m),2,25−2.34(3H,m),2.92(1H,
m),5.16−5.34(2H,m),7.14−7.22(1H,m),7.29−7.
42(2H,m),7.70(2H,d,J=7.6Hz),7.92−8.05(4H,
m). IR(CHCl3):3616,3426,3375,3010,2950,2828,2645,170
8,1672,1599,1439,1323,1161/cm. [α]D=+21.0゜(CH3OH,c=1.00,22℃). No.1j−25 CDCl3 300MHz 1.03(1H,m),1.18−2.01(13H,m),2.20(1H,bs),2.2
7(2H,t,J=7.4Hz),3.08(1H,m),3.66(3H,s),5.11
(1H,d,J=6.6Hz),5.14−5.34(2H,m),7.54−7.62(3
H,m),8.04−8.32(6H,m). IR(CHCl3):3384,3278,1726,1605,1484,1448,1331,116
1/cm. No.1j−26 CDCl3+CD3OD 300MHz 1,03−2.10(14H,m),2.22(1H,m),2.31(2H,t,J=7.5
Hz),2.98(1H,m),5.23−5.38(2H,m),7.55−7.66(3
H,m),8.05−8.08(2H,m),8.14−8.18(2H,m),8.28−
8.31(2H,m). IR(Nujol):3260,2720,2660,1711,1545,1460,1317,116
3/cm. [α]D=+15.8゜(CH3OH,c=1.01,22℃). No.1j−27 [α]D=+16.7゜(CHCl3,c=1.00,23℃). No.1j−28 CDCl3 300MHz 1.01(1H,m),1.14−1.29(2H,m),1.46−2.19(11H,
m),2.33(2H,t,J=7.2Hz),2.41(1H,bs),3.18−3.21
(5H,m),3.68(3H,s),3.73−3.76(4H,m),4.37(1H,
d,J=7.2Hz),5.35−5.45(2H,m). IR(CHCl3):3392,1727,1435,1335,1148/cm. [α]D=+10.7゜(CHCl3,c=1.39,26℃). No.1j−29 CDCl3 300MHz 1.00(1H,m),1.20−1.29(2H,m),1,48−2.25(12H,
m),2.37(2H,t,J=7.2Hz),3.17−3.22(5H,m),3.74
−3.79(4H,m),4.79(1H,d,J=7.8Hz),5.34−5.54(2
H,m). IR(CHCl3):3470,3390,3270,2675,1709,1455,1420,131
5,1147/cm. [α]D=+16.8゜(CHCl3,c=1.42,26℃). No.1k−1 [α]D=−25.4゜(CHCl3,c=1.08,23℃). No.1k−2 CDCl3 200MHz 1.07−2.28(14H,m),2.32(2H,t,J=7.4Hz),2.63(1
H,m),3.63(3H,s),3.93(1H,m),5.30−5.52(2H,
m),6.35(1H,d,J=7.0Hz),7.48−7.60(3H,m),7.88
−8.02(6H,m). IR(CHCl3):3438,3002,2946,2868,1727,1652,1514,148
5,1363,1310,1245,1154/cm. [α]D==−80.4゜(CHCl3,c=1.01,24.0℃)。
No.1k−3 CDCl3 200MHz 1.10−2.26(14H,m),2.37(2H,t,J=7.2Hz),2.60(1
H,m),3.93(1H,m),5.30−5.50(2H,m),6.33(1H,d,J
=7.5Hz),7.48−7.58(3H,m),7.88−7.99(6H,m). IR(CHCl3):3446,3004,2952,2874,1709,1652,1515,148
5,1305,1153/cm. [α]D==−96.4゜(CHCl3,c=1.05,23.0℃)。
H,m),3.93(1H,m),5.30−5.50(2H,m),6.33(1H,d,J
=7.5Hz),7.48−7.58(3H,m),7.88−7.99(6H,m). IR(CHCl3):3446,3004,2952,2874,1709,1652,1515,148
5,1305,1153/cm. [α]D==−96.4゜(CHCl3,c=1.05,23.0℃)。
No.1k−4 CDCl3 300MHz 1.05−2.17(14H,m),2.38(2H,t,J=7.2Hz),2.52(1
H,m),3.81(1H,m),5.33−5.50(2H,m),6.08(1H,d,J
=7.6Hz),7.39−7.53(3H,m),7.57−7.62(6H,m). IR(CHCl3):3420,3250,3008,2948,2870,2660,2208,173
5(sh),1705,1640,1500/cm. [α]D=−21.9±0.6゜(CHCl3,c=1.02,22℃). No.1k−5 CDCl3 300MHz 1.05−2.14(14H,m),2.38(2H,t,J=7.2Hz),2.51(1
H,m),3.81(1H,m),5.34−5.46(2H,m),6.07(1H,d,J
=7.6Hz),7.33−7.56(5H,m). IR(CHCl3):3422,3250,3010,2950,2876,2664,2558,221
0,1735(sh),1705,1645,1502,1441,1410,1307,1276/c
m. [α]D=−63.6±1.9゜(CHCl3,c=0.56,22℃). No.1k−6 CDCl3 300MHz 1.04−2.24(14H,m),2.36(2H,t,J=7.5Hz),2.58(1
H,m),3.88(1H,m),5.30−5.43(2H,m),6.21(1H,d,J
=7.2Hz),7.41−7.49(3H,m),7.73−7.77(2H,m). IR(CHCl3):3447,3011,2955,1708,1653,1603,1578,151
5,1486,1457,1312,1211,1164/cm. [α]D=−60.3゜(CHCl3,C=1.00,23℃). No.1k−7 CDCl3 300MHz 1.04−2.22(14H,m),2.36(2H,t,J=7.2Hz),2.57(1
H,m),3.87(1H,m),5.30−5.44(2H,m),6.17(1H,d,J
=8.7Hz),6.99−7.40(7H,m),7.73(2H,d,J=7.5H
z). IR(CHCl3):3449,3013,2955,1739,1708,1651,1609,158
8,1522,1487,1243,1227,1169/cm. [α]D=−60.2゜(CHCl3,c=0.92,23℃). No.1k−8 CDCl3 300MHz 1.04−2.25(14H,m),2.34(2H,t,J=7.5Hz),2.56(1
H,m),3.87(1H,m),5.30−5.44(2H,m),6.19(1H,d,J
=7.5Hz),6.83−6.94(6H,m),7.69(2H,d,J=8.7H
z). IR(CHCl3):3599,3455,3012,2955,1711,1644,1604,157
7,1524,1507,1492,1290,1236,1197,1170/cm. [α]D=−47.7゜(CHCl3,C=1.01,22℃). No.1k−9 CDCl3 300MHz 1.04−2.20(14H,m),2.31(3H,s),2.36(2H,t,J=7.2
Hz),2.56(1H,m),3.86(1H,m),5.30−5.43(2H,m),
6.16(1H,d,J=7.2Hz),7.00−7.11(6H,m),7.74(2H,
d,J=8.7Hz). IR(CHCl3):3450,3010,2955,1750,1709,1651,1609,159
6,1523,1489,1370,1247,1227,1183/cm. [α]D=−54.7゜(CHCl3,C=1.01,22℃). No.1k−10 CDCl3 300MHz 1.04−2.22(14H,m),2.35(2H,t,J=7.2Hz),2.56(1
H,m),3.82(3H,s),3.86(1H,m),5.30−5.43(2H,
m),6.17(1H,d,J=6.9Hz),6.89−7.01(6H,m),7.70
(2H,d,J=8.7Hz). IR(CHCl3):3023,2955,1742,1708,1649,1613,1602,157
7,1522,1507,1490,1227,1210,1170/cm. [α]D=−58.1゜(CHCl3,c=1.01,22℃). No.1m−1 CDCl3 300MHz 1.06−2.25(14H,m),2.32(2H,t,J=7.4Hz),2.61(1
H,m),3.63(3H,s),3.91(1H,m),5.33−5.47(2H,
m),6.24(1H,d,J=6.9Hz),7.35−7.38(3H,m),7.53
−7.60(4H,m),7.75−7.78(2H,m)。
H,m),3.81(1H,m),5.33−5.50(2H,m),6.08(1H,d,J
=7.6Hz),7.39−7.53(3H,m),7.57−7.62(6H,m). IR(CHCl3):3420,3250,3008,2948,2870,2660,2208,173
5(sh),1705,1640,1500/cm. [α]D=−21.9±0.6゜(CHCl3,c=1.02,22℃). No.1k−5 CDCl3 300MHz 1.05−2.14(14H,m),2.38(2H,t,J=7.2Hz),2.51(1
H,m),3.81(1H,m),5.34−5.46(2H,m),6.07(1H,d,J
=7.6Hz),7.33−7.56(5H,m). IR(CHCl3):3422,3250,3010,2950,2876,2664,2558,221
0,1735(sh),1705,1645,1502,1441,1410,1307,1276/c
m. [α]D=−63.6±1.9゜(CHCl3,c=0.56,22℃). No.1k−6 CDCl3 300MHz 1.04−2.24(14H,m),2.36(2H,t,J=7.5Hz),2.58(1
H,m),3.88(1H,m),5.30−5.43(2H,m),6.21(1H,d,J
=7.2Hz),7.41−7.49(3H,m),7.73−7.77(2H,m). IR(CHCl3):3447,3011,2955,1708,1653,1603,1578,151
5,1486,1457,1312,1211,1164/cm. [α]D=−60.3゜(CHCl3,C=1.00,23℃). No.1k−7 CDCl3 300MHz 1.04−2.22(14H,m),2.36(2H,t,J=7.2Hz),2.57(1
H,m),3.87(1H,m),5.30−5.44(2H,m),6.17(1H,d,J
=8.7Hz),6.99−7.40(7H,m),7.73(2H,d,J=7.5H
z). IR(CHCl3):3449,3013,2955,1739,1708,1651,1609,158
8,1522,1487,1243,1227,1169/cm. [α]D=−60.2゜(CHCl3,c=0.92,23℃). No.1k−8 CDCl3 300MHz 1.04−2.25(14H,m),2.34(2H,t,J=7.5Hz),2.56(1
H,m),3.87(1H,m),5.30−5.44(2H,m),6.19(1H,d,J
=7.5Hz),6.83−6.94(6H,m),7.69(2H,d,J=8.7H
z). IR(CHCl3):3599,3455,3012,2955,1711,1644,1604,157
7,1524,1507,1492,1290,1236,1197,1170/cm. [α]D=−47.7゜(CHCl3,C=1.01,22℃). No.1k−9 CDCl3 300MHz 1.04−2.20(14H,m),2.31(3H,s),2.36(2H,t,J=7.2
Hz),2.56(1H,m),3.86(1H,m),5.30−5.43(2H,m),
6.16(1H,d,J=7.2Hz),7.00−7.11(6H,m),7.74(2H,
d,J=8.7Hz). IR(CHCl3):3450,3010,2955,1750,1709,1651,1609,159
6,1523,1489,1370,1247,1227,1183/cm. [α]D=−54.7゜(CHCl3,C=1.01,22℃). No.1k−10 CDCl3 300MHz 1.04−2.22(14H,m),2.35(2H,t,J=7.2Hz),2.56(1
H,m),3.82(3H,s),3.86(1H,m),5.30−5.43(2H,
m),6.17(1H,d,J=6.9Hz),6.89−7.01(6H,m),7.70
(2H,d,J=8.7Hz). IR(CHCl3):3023,2955,1742,1708,1649,1613,1602,157
7,1522,1507,1490,1227,1210,1170/cm. [α]D=−58.1゜(CHCl3,c=1.01,22℃). No.1m−1 CDCl3 300MHz 1.06−2.25(14H,m),2.32(2H,t,J=7.4Hz),2.61(1
H,m),3.63(3H,s),3.91(1H,m),5.33−5.47(2H,
m),6.24(1H,d,J=6.9Hz),7.35−7.38(3H,m),7.53
−7.60(4H,m),7.75−7.78(2H,m)。
IR(CHCl3):3438,3008,2946,2875,2212,1732,1650,160
5,1519,1496/cm. [α]D=+76゜(CHCl3,c=1.39,24℃) No.1m−2 CDCl3 300MHz 1.05−2.20(14H,m),2.36(2H,t,J=6.2Hz),2.59(1
H,m),3.89(1H,m),5.29−5.48(2H,m),6.26(1H,d,J
=7.0Hz),7.26−7.38(3H,m),7.52−7.60(4H,m),7.
73−7.77(2H,m)。
5,1519,1496/cm. [α]D=+76゜(CHCl3,c=1.39,24℃) No.1m−2 CDCl3 300MHz 1.05−2.20(14H,m),2.36(2H,t,J=6.2Hz),2.59(1
H,m),3.89(1H,m),5.29−5.48(2H,m),6.26(1H,d,J
=7.0Hz),7.26−7.38(3H,m),7.52−7.60(4H,m),7.
73−7.77(2H,m)。
IR(CHCl3):3444,3012,2952,2874,2664,2214,1718(s
h),1708,1649,1605,1520,1498/cm. [α]D=+81.4゜(CHCl3,c=1.01,23℃) No.1m−3 CDCl3 300MHz 1.06−2.23(14H,m),2.32(2H,t,J=7.0Hz),2.62(1
H,m),3.63(3H,s),3.93(1H,m),5.30−5.50(2H,
m),6.28(1H,d,J=7.0Hz),7.38−7.51(3H,m),7.58
−7.67(4H,m),7.83−7.88(2H,m)。
h),1708,1649,1605,1520,1498/cm. [α]D=+81.4゜(CHCl3,c=1.01,23℃) No.1m−3 CDCl3 300MHz 1.06−2.23(14H,m),2.32(2H,t,J=7.0Hz),2.62(1
H,m),3.63(3H,s),3.93(1H,m),5.30−5.50(2H,
m),6.28(1H,d,J=7.0Hz),7.38−7.51(3H,m),7.58
−7.67(4H,m),7.83−7.88(2H,m)。
IR(CHCl3):3438,3008,2948,2875,1783(w),1727,16
50,1608,1580(w),1523,1501,1482/cm. [α]D=+59゜(CHCl3,c=1.49,25℃) No.1m−4 CDCl3 300MHz 1.08−2.25(14H,m),2.36(2H,t,J=7.4Hz),2.59(1
H,m),3.91(1H,m),5.28−5.48(3H,m),6.29(1H,d,J
=7.4Hz),7.38−7.50(3H,m),7.61−7.67(4H,m),7.
81−7.86(2H,m). IR(CHCl3):3436,3010,2948,2868,1727,1715(sh)164
9,1615(w),1524,1502,1482,1372/cm. [α]D=+72゜(CHCl3,c=0.98,25℃) No.1m−5 CDCl3 300MHz 1.09−2.20(14H,m),2.32(2H,t,J=7.2Hz),2.63(1
H,m),3.63(3H,s),3.92(1H,m),5.31−5.51(2H,
m),6.35(1H,d,J=7.0Hz),7.51−7.60(3H,m),7.92
−7.97(6H,m). IR(CHCl3):3436,3008,2946,2875,1727,1652,1608
(w),1515,1484/cm. [α]D=+82゜(CHCl3,c=0.99,25℃) No.1m−6 CDCl3 300MHz 1.09−2.23(14H,m),2.37(2H,t,J=7.2Hz),2.60(1
H,m),3.92(1H,m),5.30−5.49(2H,m),6.32(1H,d,J
=7.4Hz),7.51−7.55(3H,m),7.85−7.98(6H,m). IR(CHCl3):3436,3010,2950,2875,2670,1727,1715(s
h)1650,1605(w),1515,1484/cm. [α]D=+84゜(CHCl3,c=1.54,25℃) No.1m−7 CDCl3 300MHz 1.03−2.18(14H,m),2.32(2H,t,J=7.4Hz),2.59(1
H,m),3.64(3H,s),3.89(1H,m),5.29−5.49(2H,
m),6.16(1H,d,J=7.8Hz),6.98−7.06(4H,m),7.14
−7.20(1H,m),7.34−7.41(2H,m),7.73−7.78(2H,
m). IR(CHCl3):3438,3008,2946,2868,1727,1648,1610,158
6,1519,1485/cm. [α]D=+54゜(CHCl3,c=1.29,25℃). No.1m−8 CDCl3 300MHz 1.06−2.21(14H,m),2.36(2H,t,J=7.5Hz),2.58(1
H,m),3.88(1H,m),5.31−5.46(2H,m),6.17(1H,d,J
=6.9Hz),6.99−7.05(4H,m),7.15−7.21(1H,m),7.
36−7.41(2H,m),7.72−7.75(2H,m). IR(CHCl3):3436,3010,2948,2868,2675,1730(sh),17
09,1647,1608,1586,1520,1485/cm. [α]D=+56゜(CHCl3,c=0.97,25℃) No.1m−9 CDCl3 300MHz 1.05−2.18(14H,m),2.29−2.34(5H,m),2.59(1H,
m),3.64(3H,s),3.89(1H,m),5.32−5.46(2H,m),
6.16(1H,d,J=7.5Hz),7.00−7.11(6H,m),7.74−7.7
7(2H,m). IR(CHCl3):3440,3010,2946,2868,1729,1649,1595,151
9,1488/cm. [α]D=+47゜(CHCl3,c=0.82,25℃). No.1m−10 CDCl3 300MHz 1.04−2.20(14H,m),2.31−2.39(5H,m),2.57(1H,
m),3.87(1H,m),5.28−5.47(2H,m),6.17(1H,d,J=
7.0Hz),6.99−7.12(6H,m),7.72−7.76(2H,m). IR(CHCl3):3674,3572,3438,3010,2948,2868,2626,174
8,1710,1648,1615,1595,1520,1489/cm. [α]D=+51゜(CHCl3,c=0.91,25℃) No.1m−11 CDCl3 300MHz 1.04−2.16(14H,m),2.31(2H,t,J=7.2Hz),2.59(1
H,m),3.63(3H,s),3.89(1H,m),5.29−5.49(2H,
m),6.24(1H,d,J=7.4Hz),6.54(1H,s),6.83−6.93
(6H,m),7.69−7.73(2H,m). IR(CHCl3):3674,3588,3438,3296,3010,2946,2868,172
5,1646,1603,1520,1504,1489/cm. [α]D=+51゜(CHCl3,c=0.91,25℃) No.1m−12 CDCl3 300MHz 1.04−2.21(14H,m),2.33(2H,t,J=8.0Hz),2.56(1
H,m),3.87(1H,m),5.28−5.48(2H,m),6.23(1H,d,J
=8.0Hz),6.75(1H,m),6.87−6.94(6H,m),7.66−7.
71(2H,m),9.63(1H,bs). IR(CHCl3):3674,3582,3436,3275,3010,2950,2868,267
5,1727,1710(sh),1643,1603,1522,1504,1490/cm. [α]D=+30゜(CHCl3,c=0.97,25℃) No.1m−13 CDCl3 300MHz 1.01−2.18(14H,m),2.31(2H,t,J=7.4Hz),2.58(1
H,m),3.63(3H,s),3.82(3H,s),3.89(1H,m),5.29
−5.48(2H,m),6.14(1H,d,J=7.0Hz),6.88−7.02(6
H,m),7.70−7.74(2H,m). IR(CHCl3):3442,3402,3004,2946,2868,1727,1648,160
0,1518,1499/cm. [α]D=+42゜(CHCl3,c=1.82,26℃) No.1m−14 CDCl3 300MHz 1.05−2.21(14H,m),2.35(2H,t,J=7.2Hz),2.55(1
H,m),3.82(3H,s),3.88(1H,m),5.27−5.46(2H,
m),6.16(1H,d,J=7.2Hz),6.88−7.02(6H,m),7.68
−7.73(2H,m). IR(CHCl3):3438,3012,2948,2870,2650,1730(sh),17
09,1647,1615(sh)1601,1519,1492/cm. [α]D=+64゜(CHCl3,c=0.70,25℃) No.1m−15 CDCl3 300MHz 1.05−2.20(14H,m),2.29−2.36(5H,m),2.62(1H,
m),3.63(3H,s),3.92(1H,m),5.30−5.50(2H,m),
6.25(1H,d,J=7.2Hz),7.16−7.21(2H,m),7.59−7.6
4(4H,m),7.83−7.87(2H,m). IR(CHCl3):3446,3010,2946,2868,1745(sh),1728,16
50,1615,1525,1507,1486/cm. [α]D=+65.0゜(CHCl3,c=1.02,23℃) No.1m−16 CDCl3 300MHz 1.08−2.21(14H,m),2.34−2.40(5H,m),2.59(1H,
m),3.90(1H,m),5.29−5.48(2H,m),6.29(1H,d,J=
7.0Hz),7.18(2H,d,J=8.6Hz),7.58−7.64(4H,m),
7.83(2H,d,J=8.2Hz). IR(CHCl3):3438,3012,2948,2870,2622,1749,1710,164
9,1610,1526,1508,1487/cm. [α]D=+66゜(CHCl3,c=1.21,24℃) No.1m−17 CDCl3 300MHz 1.06−2.19(14H,m),2.32(2H,t,J=7.2Hz),2.62(1
H,m),3.63(3H,s),3.93(1H,m),5.30−5.50(2H,
m),6.32(1H,d,J=7.6Hz),6.41(1H,s),6.94(2H,d,
J=9.0Hz),7.47(2H,d,J=9.0Hz),7.58(2H,d,J=8.6
Hz),7.81(2H,d,J=8.6Hz). IR(CHCl3):3580,3434,3284,3010,2946,2868,1726,164
6,1606,1528,1490/cm. [α]D=+62.4゜(CHCl3,c=1.01,23℃) No.1m−18 CDCl3+CD3OD 300MHz 1.11−2.18(14H,m),2.32(2H,t,J=7.4Hz),2.59(1
H,m),3.88(1H,m),5.30−5.49(2H,m),6.55(1H,d,J
=7.0Hz),6.92(2H,d,J=8.6Hz),7.47(2H,d,J=8.6H
z),7.59(2H,d,J=8.6Hz),7.79(2H,d,J=8.2Hz). IR(Nujol):3398,3175,2725,1696,1635,1601,1531,150
1/cm. [α]D=+99.5゜(CH3OH,c=1.011,25℃) No.1m−19 CDCl3 300MHz 1.05−2.20(14H,m),2.32(2H,t,J=7.4Hz),2.61(1
H,m),3.63(3H,s),3.86(3H,s),3.94(1H,m),5.30
−5.50(2H,m),6.24(1H,d,J=7.0Hz),6.99(2H,d,J
=8.6Hz),7.53−7.63(4H,m),7.82(2H,d,J=8.6H
z). IR(CHCl3):3440,3006,2946,2875,1726,1649,1606,152
7,1510,1489/cm. [α]D=+68゜(CHCl3,c=0.88,26℃) No.1m−20 CDCl3 300MHz 1.09−2.20(14H,m),2.35(2H,t,J=7.3Hz),2.58(1
H,m),3.85(3H,s),3.89(1H,m),5.28−5.48(2H,
m),6.35(1H,d,J=7.2Hz),6.98(2H,d,J=8.8Hz),7.
51−7.61(4H,m),7.81(2H,d,J=8.4Hz),8.34(1H,b
s). IR(CHCl3):3446,3012,2952,2881,2640,1730(sh),17
07,1647,1606,1527,1510,1489/cm. [α]D=+83゜(CHCl3,c=1.00,25℃). No.1m−21 CDCl3 300MHz 1.05−2.14(14H,m),2.37(2H,t,J=7.2Hz),2.51(1
H,m),3.81(1H,m),5.34−5.46(2H,m),6.11(1H,d,J
=7.5Hz),7.33−7.48(3H,m),7.53−7.55(2H,m). IR(CHCl3):3420,3250,3008,2948,2870,2660,2210,173
5(sh),1705,1645,1503,1441,1409/cm. [α]D=+59.2±1.0゜(CHCl3,c=1.023,22℃). No.1m−22 CDCl3 300MHz 1.05−2.17(14H,m),2.37(2H,t,J=7.2Hz),2.52(1
H,m),3.82(1H,m),5.32−5.47(2H,m),6.20(1H,d,J
=7.6Hz),7.38−7.53(3H,m),7.58−7.61(6H,m),9.
11(1H,bs). IR(CHCl3):3420,3250,3010,2984,2870,2675,2208,173
0(sh),1705,1640,1500,1406/cm. [α]D=+57.4゜(CHCl3,c=1.83,23℃). No.1m−23 CDCl3 300MHz 1.05−2.18(14H,m),2.31(2H,t,J=7.5Hz),2.60(1
H,m),3.63(3H,s),3.90(1H,m),5.32−5.47(2H,
m),6.22(1H,d,J=6.9Hz),7.40−7.49(3H,m),7.76
−7.79(2H,m). IR(CHCl3):3438,3008,2946,2868,1727,1651,1603,158
5,1512,1484/cm. [α]D=+52゜(CHCl3,c=1.49,25℃). No.1m−24 CDCl3 300MHz 1.05−2.21(14H,m),2.36(2H,t,J=7.2Hz),2.57(1
H,m),3.89(1H,m),5.28−5.47(2H,m),6.22(1H,d,J
=7.0Hz),7.39−7.55(3H,m),7.73−7.79(2H,m). IR(CHCl3):3676,3572,3436,3010,2948,2875,1730(s
h),1709,1650,1600,1580,1514,1484/cm. [α]D=+57゜(CHCl3,c=0.97,26℃). No.1m−25 CDCl3 300MHz 1.04−2.18(14H,m),2.28−2.35(5H,m),2.59(1H,
m),3.62(3H,s),3.88(1H,m),5.29−5.49(2H,m),
6.20(1H,d,J=7.2Hz),7.15(2H,d,J=9.0Hz),7.80
(2H,d,J=8.8Hz). IR(CHCl3):3436,3010,2946,2868,1752,1727,1653,160
2,1519,1491/cm. [α]D=+53゜(CHCl3,c=1.63,25℃). No.1m−26 CDCl3 300MHz 1.05−2.19(14H,m),2.32−2.38(5H,m),2.56(1H,
m),3.88(1H,m),5.29−5.47(2H,m),6.25(1H,d,J=
7.4Hz),7.15(2H,d,J=9.0Hz),7.78(2H,d,J=8.6H
z). IR(CHCl3):3434,3016,3006,2948,2880,2622,1752,173
0(sh),1710,1651,1605,1520,1492/cm. [α]D=+58゜(CHCl3,c=3.68,24℃) No.1m−27 CDCl3 300MHz 1.05−2.16(14H,m),2.30(2H,t,J=7.5Hz),2.57(1
H,m),3.62(3H,s),3.87(1H,m),5.27−5.47(2H,
m),6.32(1H,d,J=7.4Hz),6.85(2H,d,J=8.6Hz),7.
62(2H,d,J=8.6Hz),8.35(1H,s). IR(CHCl3):3580,3450,3216,3010,2946,2868,1726,164
0,1608,1584,1528,1496/cm. [α]D=+56.2゜(CHCl3,c=0.713,23℃) No.1m−28 CDCl3 200MHz 1.10−2.25(14H,m),2.32(2H,t,J=7.2Hz),2.55(1
H,bs),3.82−3.93(1H,m),5.27−5.47(2H,m),6.25
(1H,d,J=7.4Hz),6.86(2H,d,J=8.6Hz),7.62(2H,
d,J=8.6Hz). IR(CHCl3):3438,3242,2675,1730(sh),1708,1639,16
07,1585/cm. No.1m−29 CDCl3 300MHz 1.05−2.18(14H,m),2.31(2H,t,J=7.4Hz),2.58(1
H,m),3.64(3H,s),3.85(3H,s),3.89(1H,m),5.29
−5.48(2H,m),6.14(1H,d,J=6.6Hz),6.92(2H,d,J
=9.0Hz),7.74(2H,d,J=9.0Hz). IR(CHCl3):3445,3008,2946,2868,1727,1646,1606,157
8,1523,1493/cm. [α]D=+53゜(CHCl3,c=2.03,24℃) No.1m−30 CDCl3 300MHz 1.04−2.21(14H,m),2.36(2H,t,J=7.3Hz),2.56(1
H,m),3.85(3H,s),3.88(1H,m),5.27−5.46(2H,
m),6.15(1H,d,J=7.2Hz),6.92(2H,d,J=8.6Hz),7.
73(2H,d,J=8.6Hz). IR(CHCl3):3440,3010,2950,2870,2645,1727,1710(s
h),1646,1606,1575,1524,1494/cm. [α]D=+62゜(CHCl3,c=1.01,24℃). No.1m−31 CDCl3+CD3OD 300MHz 1.16−2.20(14H,m),2.31(2H,t,J=7.2Hz),2.59(1
H,m),3.85(1H,m),5.31−5.51(2H,m),7.13−7.21
(1H,m),7.31−7.42(2H,m),7.68−7.93(6H,m). IR(Nujol):3344,3175,2715,2675,1699,1631,1566/cm. [α]D=+67゜(CH3OH,c=1.01,24℃). No.1m−32 CDCl3 200MHz 1.09−2.23(14H,m),2.33(2H,t,J=7.1Hz),2.57(1
H,bs),3.40−3.93(9H,m),4.41(1H,bs),5.29−5.48
(2H,m),6.44(1H,d,J=7.4Hz),7.43(2H,d,J=8.2H
z),7.80(2H,d,J=7.8Hz). IR(CHCl3)3434,3354,1726,1720(sh),1660(sh),16
26/cm. No.1m−33 CDCl3 200MHz 1.14−2.25(14H,m),2.37(2H,t,J=7.3Hz),2.64(1
H,bs),3.93−4.01(1H,m),5.30−5.51(2H,m),6.47
(1H,d,J=7.4Hz),7.63−7.74(2H,m),7.79(2H,s),
7.89−7.93(1H,m),8.00(1H,dd,J=2.3,1.0Hz),8.30
(1H,d,J=1.0Hz),8.65−8.73(2H,m). IR(CHCl3):3450,2675,1728,1707,1649,1528,1509/cm. [α]D=+82.8±1.2゜(CHCl3,c=1.01,23℃). No.2a−1 [α]D=+69.0゜(MeOH,c=1.01,25℃) No.2a−2 CDCl3 300MHz 0.99(1H,d,J=10.2Hz),1.15and1.24(each 3H,each
s),1.50−2.50(14H,m),4.30(1H,m),5.35−5.52(2
H,m),6.32(1H,d,J=8.7Hz),7.36−7.49(3H,m),7.5
8−7.62(2H,m),7.66and7.80(each 2H,each d,J=8.7
Hz). IR(CHCl3):3116,3014,2925,2870,2663,1708,1651,161
0,1524,1504,1484,1472/cm. [α]D=+64.1゜(MeOH,c=1.02,25℃). No.2a−3 [α]D=+76.6゜(MeOH,c=1.18,26℃). No.2a−4 CDCl3 300MHz 0.99(1H,d,J=10.2Hz),1.15and1.25(each 3H,each
s),1.64−2.51(14H,m),4.31(1H,m),5.36−5.53(2
H,m),6.33(1H,d,J=8.4Hz),7.50−7.56(3H,m),7.8
5−7.98(6H,m). IR(CHCl3):3515,3452,3014,2925,2870,1740,1708,165
4,1517,1486,1470/cm. [α]D=+79.5゜(MeOH,c=1.18,22℃). No.2a−5 CD3OD 300MHz 0.98(1H,d,J=9.9Hz),1.18and1.25(each 3H,each
s),1.56−1.71(3H,m),1.98−2.40(11H,m),4.17(1
H,m),5.41−5.52(2H,m),7.52−7.61(3H,m),7.91−
8.01(6H,m). IR(CHCl3):3416,3063,2983,2921,2869,1704,1643,156
6,1518,1488,1408/cm. [α]D=+62.0゜(MeOH,c=1.00,25℃). No.2a−6 [α]D=+64.1゜(MeOH,c=1.01,25℃). No.2a−7 [α]D=+65.3゜(MeOH,c=0.99,25℃). No.2a−8 [α]D=+74.0゜(MeOH,c=1.01,25℃). No.2a−9 [α]D=+71.0゜(MeOH,c=1.10,25℃). No.2a−10 [α]D=+74.7゜(MeOH,c=1.00,25℃). No.2a−11 [α]D=+72.1゜(MeOH,c=1.00,25℃). No.2a−12 [α]D=+53.1゜(CHCl3,c=1.01,26℃). m.p.155.0−156.0℃ No.2a−13 CDCl3 300MHz 0.98(1H,d,J=10.2Hz),1.18and1.25(each 3H,each
s),1.63−2.40(14H,m),4.30(1H,m),5.46−5.58(2
H,m),6.44(1H,d,J=8.4Hz),7.49and7.77(each 2H,e
ach d,J=8.7Hz),7.54(1H,s). IR(CHCl3):3689,3378,3028,3014,2924,1713,1652,160
2,1522,1496/cm. [α]D=+78.3゜(MeOH,c=0.84,25℃). m.p.205.0−206.0℃ No.2a−14 [α]D=+72.5゜(MeOH,c=1.07,25℃). No.2a−15 CDCl3 300MHz 0.99(1H,d,J=9.9Hz),1.14and1.24(each 3H,each
s),1.55−2.44(14H,m),4.27(1H,m),5.30−5.50(2
H,m),6.29(1H,d,J=9.0Hz),7.11and7.20(each 1H,e
ach d,J=16.2Hz),7.29−7.55(5H,m),7.57and7.72
(each 2H,each d,J=8.7Hz). IR(CHCl3):3453,3083,3022,3013,2925,2870,1708,165
0,1607,1560,1522,1496/cm. [α]D=+72.3゜(MeOH,c=1.00,27℃). m.p.115.0−117.0℃ No.2a−16 CDCl3 300MHz 0.92(1H,d,J=10.2Hz),1.11and1.23(each 3H,each
s),1.50−2.48(14H,m),3.62(3H,s),4.29(1H,m),
5.30−5.50(2H,m),6.20(1H,d,J=8.7Hz),6.59and6.
68(each 1H,each d,J=12.3Hz),7.23(5H,s),7.29an
d7.59(each 2H,each d,J=8.1Hz). IR(CHCl3):3453,3024,3016,2924,2870,1730,1651,160
7,1520,1495/cm. [α]D=+56.8゜(MeOH,c=1.04,24℃). No.2a−17 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.11and1.23(each 3H,each
s),1.50−2.38(14H,m),4.26(1H,m),5.30−5.50(2
H,m),6.23(1H,d,J=8.4Hz),6.59and6.70(each 1H,e
ach d,J=12.3Hz),7.23(5H,s),7.30and7.57(each 2
H,each d,J=8.7Hz). IR(CHCl3):3452,3081,3019,3014,2925,2870,2665,170
8,1650,1607,1521,1495/cm. [α]D=+61.6゜(MeOH,c=1.00,27℃). No.2a−18 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.11and1.23(each 3H,each
s),1.50−2.50(14H,m),3.61(3H,s),4.31(1H,m),
5.35−5.51(2H,m),6.33(1H,d,J=8.4Hz),7.48−7.6
4(4H,m),7.79−7.83(2H,m),7.91(1H,dt,J=1.5and
7.8Hz),8.01(1H,dt,J=1.5and7.8Hz),8.13(1H,t,J
=1.5Hz). IR(CHCl3):3450,3026,3013,2925,2870,1730,1659,160
0,1510/cm. [α]D=+56.0゜(MeOH,c=1.01,25℃). No.2a−19 CDCl3 300MHz 0.95(1H,d,J=9.9Hz),1.14and1.21(each 3H,each
s),1.53−2.60(14H,m),4.25(1H,m),5.35−5.64(2
H,m),7.21(1H,d,J=7.8Hz),7.49−7.68(4H,m),7.7
6−7.84(3H,m),8.25(1H,m),8.43(1H,m). IR(CHCl3):3382,3196,3025,3015,2925,2870,1725,165
2,1599,1577,1521/cm. [α]D=+55.9゜(MeOH,c=1.00,25℃). No.2a−20 CDCl3 300MHz 0.98(1H,d,J=10.2Hz),1.13and1.24(each 3H,each
s),1.50−2.50(14H,m),3.62(3H,s),4.31(1H,m),
5.35−5.51(2H,m),6.24(1H,d,J=8.4Hz),7.40−7.5
2(3H,m),7.71−7.76(2H,m). IR(CHCl3):3453,3025,3013,2925,2870,1730,1753,157
9,1514,1486/cm. [α]D=+61.2゜(MeOH,c=1.04,25℃). No.2a−21 CDCl3 300MHz 0.98(1H,d,J=10.2Hz),1.13and1.23(each 3H,each
s),1.52−2.50(14H,m),4.28(1H,m),5.34−5.51(2
H,m),6.27(1H,d,J=8.7Hz),7.41−7.53(3H,m),7.7
1−7.74(2H,m). IR(CHCl3):3452,3063,3027,3014,2925,2871,1708,165
2,1578,1515,1486/cm. [α]D=+62.0゜(MeOH,c=1.01,27℃). No.2a−22 d6−DMSO 300MHz 0.86(1H,d,J=9.9Hz),1.10and1.16(each 3H,each
s),1.42−1.52(3H,m),1.85−2.46(11H,m),3.98(1
H,m),5.32−5.43(2H,m),7.41(3H,m),7.88(2H,d,J
=6.6Hz),8.19(1H,d,J=6.6Hz). IR(KBr):3367,3060,2984,2922,2868,1634,1563,1529,
1487/cm. [α]D=+47.7゜(MeOH,c=1.00,25℃). No.2a−23 [α]D=+62.7゜(MeOH,c=1.01,27℃). No.2a−24 CDCl3 300MHz 0.99(1H,d,J=10.2Hz),1.14and1.25(each 3H,each
s),1.52−2.50(14H,m),4.31(1H,m),5.36−5.52(2
H,m),6.34(1H,d,J=8.4Hz),7.47−7.52(2H,m),7.5
9−7.64(1H,m),7.78−7.83(6H,m). IR(CHCl3):3449,3027,3013,2925,2869,1708,1656,159
9,1518,1493/cm. [α]D=+63.1゜(MeOH,c=1.00,25℃). No.2a−25 [α]D=+35.1゜(MeOH,c=1.00,25℃). No.2a−26 [α]D=+35.5゜(MeOH,c=1.02,25℃). No.2a−27 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.12and1.23(each 3H,each
s),1.52−2.50(14H,m),3.63(3H,s),4.29(1H,m),
5.36−5.51(2H,m),6.18(1H,d,J=8.4Hz),7.01and7.
71(each 2H,each d,J=8.7Hz),6.98−7.05(2H,m),
7.16(1H,t,J=7.5Hz),7.34−7.41(2H,m). IR(CHCl3):3455,3024,3016,2924,2870,1730,1651,158
8,1520,1487/cm. [α]D=+56.4゜(MeOH,c=1.01,25℃). No.2a−28 CDCl3 300MHz 0.98(1H,d,J=10.2Hz),1.12and1.23(each 3H,each
s),1.52−2.50(14H,m),4.26(1H,m),5.34−5.51(2
H,m),6.20(1H,d,J=9.0Hz),7.01and7.70(each 2H,e
ach d,J=9.0Hz),6.98−7.15(2H,m),7.17(1H,t,J=
7.5Hz),7.34−7.40(2H,m). IR(CHCl3):3454,3031,3018,2925,2870,1708,1650,158
8,1523,1487/cm. [α]D=+56.2゜(MeOH,c=1.00,25℃). No.2a−29 [α]D=+53.0゜(MeOH,c=1.03,25℃). No.2a−30 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.10and1.23(each 3H,each
s),1.52−2.50(14H,m),4.25(1H,m),5.30−5.50(2
H,m),6.23(1H,d,J=8.7Hz),6.36(1H,s),7.26−7.3
9(10H,m),7.60and7.68(each 2H,each d,J=8.4H
z). IR(CHCl3):3451,3088,3064,3029,3014,2925,2869,170
7,1652,1522,1495/cm. [α]D=+54.2゜(MeOH,c=1.00,25℃). No.2a−31 CDCl3 300MHz 0.98(1H,d,J=10.2Hz),1.14and1.24(each 3H,each
s),1.50−2.50(14H,m),3.63(3H,s),4.31(1H,m),
5.30−5.50(2H,m),6.26(1H,d,J=8.4Hz),6.90(1H,
d,J=7.4Hz),7.13(1H,d,J=8.7Hz),7.29(2H,t,J=
8.0Hz),7.67−7.75(5H,m),7.82(1H,s). IR(Nuj4ol):3380,3244,1723,1638,1601,1578,1535,14
95/cm. [α]D=+73.6゜(MeOH,c=0.50,26℃). m.p.133.0−134.0℃ No.2a−32 [α]D=+56.1゜(MeOH,c=1.02,26℃). No.2a−33 CDCl3 300MHz 0.95(1H,d,J=10.2Hz),1.10and1.21(each 3H,each
s),1.50−2.50(14H,m),4.25(1H,m),5.13(2H,s),
5.30−5.70(3H,m),6.41(1H,d,J=8.2Hz),6.89(1H,
s),7.09(1H,s),7.17and7.72(each 2H,each d,J=8.
2Hz),7.62(1H,s). IR(CHCl3):3450,3125,3031,3013,2925,2870,2467,191
7,1708,1654,1615,1575,1523,1497/cm. [α]D=+55.2゜(MeOH,c=1.01,26℃). No.2a−34 [α]D=+72.9゜(MeOH,c=1.03,25℃). No.2a−35 CDCl3 300MHz 0.98(1H,d,J=10.2Hz),1.13and1.24(each 3H,each
s),1.52−2.48(14H,m),4.28(1H,m),5.35−5.51(2
H,m),6.28(1H,d,J=8.7Hz),7.34−7.37(3H,m),7.5
2−7.55(2H,m),7.58and7.71(each 2H,each d,J=8.7
Hz). IR(CHCl3):3515,3452,3030,3012,2925,2870,1739,170
8,1652,1607,1555,1521,1497/cm. [α]D=+74.3゜(MeOH,c=1.01,25℃). No.2a−36 [α]D=+23.4゜(MeOH,c=1.07,25℃). No.2a−37 CDCl3 300MHz 0.83(1H,d,J=10.5Hz),0.95and1.18(each 3H,each
s),1.44−2.46(14H,m),3.92(1H,m),5.34−5.52(3
H,m),7.26−7.54(9H,m),7.62(1H,s). IR(CHCl3):3432,3310,3189,3023,3014,2924,2870,170
4,1610,1594,1523,1487/cm. [α]D=+25.3゜(MeOH,c=1.00,26℃). No.2a−38 [α]D=+70.9゜(MeOH,c=1.02,25℃). No.2a−39 [α]D=+70.6゜(MeOH,c=1.01,25℃). No.2a−40 [α]D=+74.7゜(MeOH,c=1.00,25℃). No.2a−41 [α]D=+72.1゜(MeOH,c=1.01,24℃). No.2a−42 [α]D=+69.2゜(MeOH,c=1.00,25℃). No.2a−43 [α]D=+70.8゜(MeOH,c=1.00,25℃). No.2a−44 [α]D=+60.4゜(MeOH,c=1.00,26℃). No.2a−45 CDCl3 300MHz 0.97(1H,d,J=9.9Hz),1.13and1.23(each 3H,each
s),1.55−2.52(14H,m),4.29(1H,m),5.34−5.54(2
H,m),6.33(1H,d,J=9.0Hz),7.10(1H,t,J=7.4Hz),
7.34(2H,t,J=7.4Hz),7.52(2H,m),7.68and7.75(ea
ch 2H,each d,J=8.4Hz),7.80(1H,s),8.10(1H,s),
10.09(1H,s). IR(CHCl3):3393,3195,3093,3033,3013,2925,2870,169
8,1656,1598,1537,1498/cm. [α]D=+59.4゜(MeOH,c=1.01,24℃). No.2a−46 [α]D=+63.5゜(MeOH,c=1.00,25℃). No.2a−47 CDCl3 300MHz 0.97(1H,d,J=9.9Hz),1.12and1.23(each 3H,each
s),1.54−2.48(14H,m),4.29(1H,m),5.35−5.52(2
H,m),6.32(1H,d,J=8.7Hz),7.26(1H,m),7.41(2H,
t,J=7.8Hz),7.64(2H,d,J=7.5Hz),7.73and7.77(ea
ch 2H,each d,J=8.4Hz),7.95(1H,s),9.20(1H,s),
10.38(1H,s). IR(CHCl3):3450,3339,3003,2992,2925,2870,1706,165
3,1596,1523,1495/cm. [α]D=+63.3゜(MeOH,c=1.00,25℃). No.2a−48 [α]D=+63.8゜(MeOH,c=1.00,24℃). No.2a−49 CDCl3 300MHz 1.00(1H,d,J=10.5Hz),1.17and1.26(each 3H,each
s),1.55−2.52(14H,m),4.34(1H,m),5.36−5.54(2
H,m),6.35(1H,d,J=9.0Hz),7.50−7.62(3H,m),7.9
0and8.33(each 2H,each d,J=8.4Hz),8.21(2H,m). IR(CHCl3):3451,3029,3022,3016,2925,2870,1708,165
5,1542,1508,1498,1471,1459/cm. [α]D=+63.5゜(MeOH,c=1.02,25℃). m.p.135.0−137.0℃ No.2a−50 [α]D=+68.9゜(MeOH,c=1.01,24℃). No.2a−51 d6−DMSO 300MHz 0.87(1H,d,J=9.9Hz),1.10and1.17(each 3H,each
s),1.40−1.60(3H,m),1.90−2.40(11H,m),3.98(1
H,m),5.35−5.46(2H,m),7.64(1H,s),7.65and7.91
(each 2H,each d,J=8.7Hz),8.06(1H,d,J=6.0Hz),
9.32(1H,bs). IR(KBr):3385,2962,1734,1707,1632,1529,1498/cm. [α]D=+68.4゜(MeOH,c=1.01,24℃). No.2a−52 [α]D=+76.2゜(MeOH,c=1.01,24℃). No.2a−53 [α]D=+73.9゜(MeOH,c=1.02,24℃). No.2a−54 [α]D=+68.1゜(MeOH,c=1.00,24℃). No.2a−55 [α]D=+67.8゜(MeOH,c=1.00,24℃). No.2a−56 [α]D=+65.4゜(MeOH,c=1.03,25℃). No.2a−57 [α]D=+63.4゜(MeOH,c=1.01,24℃). No.2a−58 [α]D=+66.6゜(MeOH,c=1.01,24℃). No.2a−59 [α]D=+65.5゜(MeOH,c=1.00,24℃). No.2a−60 [α]D=+60.9゜(MeOH,c=1.02,25℃). No.2a−61 CDCl3 300MHz 0.97(1H,d,J=10.0Hz),1.10and1.22(each 3H,each
s),1.50−2.50(14H,m),4.26(1H,m),5.30−5.54(2
H,m),6.28(1H,d,J=8.6Hz),6.60and6.82(each 1H,e
ach d,J=12.4Hz),7.12(2H,d,J=6.0Hz),7.25and7.6
2(each 2H,each d,J=8.6Hz),8.47(2H,d,J=6.0H
z). IR(CHCl3):3452,3027,3019,3013,2925,2870,2480,170
8,1651,1606,1520,1494/cm. [α]D=+61.6゜(MeOH,c=1.01,25℃). No.2a−62 [α]D=+72.0゜(MeOH,c=0.93,25℃). No.2a−63 CDCl3 300MHz 0.99(1H,d,J=10.2Hz),1.14and1.24(each 3H,each
s),1.50−2.50(14H,m),4.29(1H,m),5.36−5.55(2
H,m),6.35(1H,d,J=9.1Hz),7.04and7.27(each 1H,e
ach d,J=16.5Hz),7.37(2H,d,J=6.6Hz),7.56and7.7
6(each 2H,each d,J=8.4Hz),8.57(2H,d,J=6.6H
z). IR(CHCl3):3452,3024,3018,3014,2925,2870,2470,193
3,1708,1652,1605,1521,1496/cm. [α]D=+69.2゜(MeOH,c=1.01,25℃). No.2a−64 [α]D=+56.9゜(MeOH,c=1.24,25℃). No.2a−65 CDCl3 300MHz 0.98(1H,d,J=10.5Hz),1.12and1.23(each 3H,each
s),1.54−2.46(14H,m),4.27(1H,m),5.23(2H,s),
5.34−5.52(2H,m),6.26(1H,d,J=8.4Hz),7.32−7.4
5(5H,m),7.64and7.71(each 2H,each d,J=8.4Hz),
8.15(1H,s). IR(CHCl3):3452,3088,3065,3032,3013,2925,2870,170
8,1653,1611,1559,1522,1496/cm. [α]D=+61.0゜(MeOH,c=0.91,25℃). No.2a−66 [α]D=+76.0゜(MeOH,c=1.01,25℃). No.2a−67 CDCl3 300MHz 0.98(1H,d,J=10.4Hz),1.14and1.24(each 3H,each
s),1.54−2.46(14H,m),4.28(1H,m),5.32−5.53(2
H,m),6.27(1H,d,J=8.6Hz),6.92−7.31(each 1H,ea
ch d,J=16.4Hz),7.02(1H,dd,J=5.8and3.6Hz),7.12
(1H,d,J=3.6Hz),7.24(1H,d,J=5.8Hz),7.51and7.7
0(each 2H,each d,J=8.4Hz). IR(CHCl3):3453,3029,3013,2925,2870,1739,1650,160
4,1524,1515,1494/cm. [α]D=+76.2゜(MeOH,c=1.00,24℃). m.p.104.0−106.0℃ No.2a−68 [α]D=+57.7゜(MeOH,c=1.01,25℃). No.2a−69 CDCl3 300MHz 0.99(1H,d,J=10.2Hz),1.14and1.24(each 3H,each
s),1.54−2.48(14H,m),4.28(1H,m),5.34−5.53(2
H,m),6.29(1H,d,J=9.0Hz),6.54−6.74(each 1H,ea
ch d,J=12.0Hz),7.02(1H,dd,J=4.8and3.3Hz),6.97
(1H,dd,J=3.3and1.2Hz),7.13(1H,dd,J=4.8and1.2H
z),7.44and7.70(each 2H,each d,J=8.7Hz). IR(CHCl3):3453,3025,3010,2925,2870,1708,1650,160
7,1559,1523,1493/cm. [α]D=+58.4゜(MeOH,c=1.00,25℃). No.2a−70 [α]D=+48.6゜(MeOH,c=1.00,25℃). No.2a−71 CDCl3 300MHz 0.98(1H,d,J=10.2Hz),1.12and1.23(each 3H,each
s),1.52−2.46(14H,m),2.31(3H,s),4.26(1H,m),
5.33−5.52(2H,m),6.20(1H,d,J=9.3Hz),7.02−7.1
1(6H,m),7.70(2H,d,J=9.0Hz). IR(CHCl3):3460,3031,3022,3011,2925,2870,1750,170
8,1650,1608,1597,1523,1490/cm. [α]D=+48.9゜(MeOH,c=1.01,25℃). No.2a−72 [α]D=+51.2゜(MeOH,c=1.02,25℃). No.2a−73 CDCl3 300MHz 0.97(1H,d,J=9.9Hz),1.11and1.23(each 3H,each
s),1.54−2.48(14H,m),4.27(1H,m),5.32−5.52(2
H,m),6.24(1H,d,J=9.0Hz),6.83−6.94(6H,m),7.6
5(2H,d,J=9.0Hz). IR(CHCl3):3598,3451,3199,3033,3012,2925,2870,170
8,1642,1604,1524,1507,1491/cm. [α]D=+52.2゜(MeOH,c=1.01,25℃). No.2a−74 [α]D=+51.5゜(MeOH,c=0.92,25℃). No.2a−75 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.11and1.23(each 3H,each
s),1.55−2.46(14H,m),3.82(3H,s),4.25(1H,m),
5.32−5.52(2H,m),6.19(1H,d,J=8.7Hz),6.89−7.0
1(6H,m),7.65−7.68(2H,m). IR(CHCl3):3450,3025,3008,2925,2870,2837,1741,164
9,1612,1521,1505,1490/cm. [α]D=+51.1゜(MeOH,c=1.00,25℃). No.2a−76 [α]D=+60.4゜(MeOH,c=0.98,25℃). No.2a−77 CDCl3 300MHz 0.99(1H,d,J=10.5Hz),1.15and1.24(each 3H,each
s),1.54−2.48(14H,m),2.34(3H,s),4.29(1H,m),
5.32−5.54(2H,m),6.32(1H,d,J=8.4Hz),7.19and7.
60(each 2H,each d,J=8.4Hz),7.63and7.79(each 2
H,each d,J=8.4Hz). IR(CHCl3):3452,3027,3012,2925,2870,1751,1709,165
1,1611,1560,1527,1509,1489/cm. [α]D=+61.2゜(MeOH,c=1.00,25℃). No.2a−78 [α]D=+67.4゜(MeOH,c=1.01,25℃). No.2a−79 CDCl3 300MHz 0.99(1H,d,J=10.2Hz),1.15and1.24(each 3H,each
s),1.54−2.54(14H,m),4.31(1H,m),5.32−5.54(2
H,m),6.36(1H,d,J=8.2Hz),6.93and7.48(each 2H,e
ach d,J=8.6Hz),7.59and7.75(each 2H,each d,J=8.
4Hz). IR(CHCl3):3593,3448,3192,3030,3010,2925,2870,170
8,1644,1608,1591,1559,1530,1516,1491/cm. [α]D=+65.8゜(MeOH,c=1.01,25℃). No.2a−80 [α]D=+66.9゜(MeOH,c=1.01,25℃). No.2a−81 CDCl3 300MHz 0.99(1H,d,J=10.5Hz),1.15and1.24(each 3H,each
s),1.54−2.48(14H,m)3.86(3H,s),4.29(1H,m),
5.34−5.52(2H,m),6.20(1H,d,J=8.7Hz),6.99and7.
55(each 2H,each d,J=9.0Hz),7.61and7.77(each 2
H,each d,J=8.7Hz). IR(CHCl3):3450,3009,2925,2870,2838,1740,1708,165
0,1608,1557,1528,1512,1491/cm. [α]D=+66.2゜(MeOH,c=1.01,25℃). No.2a−82 [α]D=+57.7゜(MeOH,c=1.02,24℃). No.2a−83 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.12and1.23(each 3H,each
s),1.54−2.48(14H,m),2.33(3H,s),4.26(1H,m),
5.32−5.52(2H,m),6.25(1H,d,J=8.7Hz),7.16and7.
75(each 2H,each d,J=8.7Hz). IR(CHCl3):3452,3030,3022,3012,2925,2870,1754,170
9,1654,1604,1585,1522,1493/cm. [α]D=+57.4゜(MeOH,c=1.01,24℃). No.2a−84 [α]D=+57.8゜(MeOH,c=1.01,24℃). No.2a−85 CDCl3 300MHz 0.95(1H,d,J=10.2Hz),1.12and1.22(each 3H,each
s),1.54−2.48(14H,m),4.25(1H,m),5.32−5.52(2
H,m),6.28(1H,d,J=8.7Hz),6.87and7.57(each 2H,e
ach d,J=9.0Hz). IR(CHCl3):3590,3450,3166,3019,3012,2925,2871,170
8,1637,1608,1583,1531,1498/cm. [α]D=+56.0゜(MeOH,c=1.01,24℃). No.2a−86 [α]D=+59.3゜(MeOH,c=1.01,22℃). No.2a−87 CDCl3 300MHz 0.98(1H,d,J=10.0Hz),1.13and1.23(each 3H,each
s),1.54−2.48(14H,m),3.85(3H,s),4.25(1H,m),
5.32−5.53(2H,m),6.19(1H,d,J=8.8Hz),6.93and7.
69(each 2H,each d,J=9.0Hz). IR(CHCl3):3450,3030,3017,3012,2925,2870,2840,174
0,1708,1647,1606,1575,1525,1496/cm. [α]D=+58.2゜(MeOH,c=0.99,22℃). No.2a−88 [α]D=+50.9゜(MeOH,c=1.02,25℃). No.2a−89 CDCl3 300MHz 0.99(1H,d,J=10.2Hz),1.18and1.26(each 3H,each
s),1.56−2.48(14H,m),4.29(1H,m),5.36−5.54(2
H,m),7.03(1H,d,J=8.7Hz),7.21(1H,s),7.43(2H,
m),7.74(1H,ddd,J=1.8,6.9and8.7Hz),8.22(1H,dd,
J=1.8and8.1Hz). IR(CHCl3):3443,3087,3023,3014,2925,2870,1708,168
5,1658,1630,1517,1466/cm. [α]D=+57.1゜(MeOH,c=1.01,25℃). m.p.117.0−118.0℃ No.2a−90 [α]D=+54.1゜(MeOH,c=1.01,22℃). No.2a−91 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.13and1.23(each 3H,each
s),1.52−2.46(14H,m),4.24(1H,m),5.34−5.52(2
H,m),6.49−6.53(2H,m),7.11(1H,dd,J=0.9and3.6H
z),7.44(1H,dd,J=0.9and1.8Hz). IR(CHCl3):3437,3033,3022,3014,2925,2870,1739,170
8,1655,1595,1520,1472/cm. [α]D=+55.0゜(MeOH,c=1.00,22℃). No.2a−92 [α]D=+50.3゜(MeOH,c=1.00,22℃). No.2a−93 CDCl3 300MHz 0.95(1H,d,J=10.5Hz),1.12and1.23(each 3H,each
s),1.52−2.46(14H,m),4.25(1H,m),5.34−5.52(2
H,m),6.12(1H,d,J=8.7Hz),7.07(1H,dd,J=3.9and
5.1Hz),7.45−7.48(2H,m). IR(CHCl3):3450,3023,3011,2925,2870,1739,1708,164
5,1531,1501,1471/cm. [α]D=+49.1゜(MeOH,c=1.02,24℃). No.2a−94 [α]D=+51.5゜(MeOH,c=1.00,24℃). No.2a−95 CDCl3 300MHz 0.96(1H,d,J=10.5Hz),1.11and1.23(each 3H,each
s),1.52−2.46(14H,m),4.25(1H,m),5.34−5.56(2
H,m),6.14(1H,d,J=8.7Hz),7.34(2H,d,J=2.0Hz),
7.85(1H,t,J=2.0Hz). IR(CHCl3):3452,3114,3030,3013,2925,2870,1708,164
9,1535,1498,1471/cm. [α]D=+55.5゜(MeOH,c=1.00,25℃). m.p.87.0−88.0℃ No.2a−96 CD3OD 300MHz 0.94(1H,d,J=10.2Hz),1.13and1.22(each 3H,each
s),1.50−1.76(3H,m),1.94−2.39(11H,m),4.11(1
H,m),5.39−5.49(2H,m),7.43−7.51(2H,m),8.05
(1H,m). IR(KBr):3369,3084,2985,2921,2868,1630,1566,1538,
1503/cm. [α]D=+38.8゜(MeOH,c=1.01,22℃). No.2a−97 CD3OD 300MHz 0.93(1H,d,J=9.9Hz),1.13and1.22(each 3H,each
s),1.48−1.58(3H,m),1.96−2.36(11H,m),4.10(1
H,m),5.35−5.50(2H,m),7.42−7.51(2H,m),8.06
(1H,m). IR(KBr):3447,3087,2987,2922,2868,1629,1545,1501/
cm. [α]D=+52.9゜(MeOH,c=1.01,24℃). No.2a−98 [α]D=+53.2゜(MeOH,c=1.02,23℃). No.2a−99 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.12and1.22(each 3H,each
s),1.26−2.45(24H,m),4.25(2H,m),5.34−5.52(2
H,m),6.18(1H,d,J=8.7Hz),6.91and7.66(each 2H,e
ach d,J=9.0Hz). IR(CHCl3):3455,3029,3019,2939,2862,1738,1709,164
5,1605,1523,1494/cm. [α]D=+51.4゜(MeOH,c=1.00,23℃). No.2a−100 [α]D=+49.3゜(MeOH,c=1.00,24℃). No.2a−101 [α]D=+51.3゜(MeOH,c=1.00,24℃). No.2a−102 [α]D=+48.8゜(MeOH,c=1.01,23℃). No.2a−103 CDCl3 300MHz 0.94(1H,d,J=10.2Hz),1.12and1.22(each 3H,each
s),1.52−2.46(14H,m),2.48(3H,d,J=0.3Hz),4.20
(1H,m),5.32−5.54(2H,m),6.46(1H,bs),7.12(1
H,d,J=9.0Hz). IR(CHCl3):3415,3144,3029,3011,2926,2871,1708,167
1,1598,1538,14564/cm. [α]D=+49.6゜(MeOH,c=1.01,23℃). No.2a−104 [α]D=+77.0゜(MeOH,c=1.02,23℃). No.2a−105 CDCl3 300MHz 0.93(1H,d,J=9.9Hz),1.09and1.21(each 3H,each
s),1.51−2.44(14H,m),3.90(6H,s),4.20(1H,m),
5.38−5.50(2H,m),5.87(1H,d,J=9.0Hz),6.25and7.
54(each 1H,each d,J=15.6Hz),6.84(1H,d,J=8.1H
z),7.03(1H,d,J=1.8Hz),7.09(1H,dd,J=1.8and8.1
Hz). IR(CHCl3):3439,3028,3012,2937,2871,2841,1739,170
8,1661,1620,1600,1513/cm. [α]D=+77.3゜(MeOH,c=1.01,23℃). No.2a−106 [α]D=+67.0゜(MeOH,c=1.00,25℃). No.2a−107 [α]D=+66.6゜(MeOH,c=1.01,24℃). m.p.168.0−170.0℃ No.2a−108 [α]D=+61.8゜(MeOH,c=1.00,22℃). No.2a−109 CDCl3 300MHz 0.96(1H,d,J=10.2Hz),1.10and1.22(each 3H,each
s),1.51−2.45(14H,m),4.25(1H,m),5.35−5.49(2
H,m),6.21(1H,d,J=8.7Hz),7.25and7.60(each 2H,e
ach d,J=8.7Hz),7.33−7.41(5H,s). IR(CHCl3):3453,3062,3028,3014,2925,2870,1739,170
8,1651,1594,1557,1515,1481/cm. [α]D=+61.0゜(MeOH,c=1.01,22℃). No.2a−110 CD3OD 300MHz 0.94(1H,d,J=9.9Hz),1.13and1.22(each 3H,each
s),1.54−2.37(14H,m),4.12(1H,m),5.38−5.49(2
H,m),7.25and7.68(each 2H,each d,J=8.7Hz),7.41
(5H,s). IR(KBr):3435,3058,2986,2920,2866,1635,1595,1562,
1521,1482,1439,1411/cm. [α]D=+47.3゜(MeOH,c=1.01,23℃). No.2a−111 [α]D=+65.6゜(MeOH,c=1.01,24℃). No.2a−112 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.12and1.23(each 3H,each
s),1.51−2.46(14H,m),4.27(1H,m),5.35−5.50(2
H,m),6.22(1H,d,J=8.4Hz),7.40and7.66(each 2H,e
ach d,J=9.0Hz). IR(CHCl3):3439,3028,3012,2937,2871,2841,1739,170
8,1661,1620,1600,1513/cm. [α]D=+65.6゜(MeOH,c=1.01,22℃). No.2a−113 [α]D=+59.6゜(MeOH,c=1.00,24℃). No.2a−114 CDCl3 300MHz 0.98(1H,d,J=10.2Hz),1.12and1.24(each 3H,each
s),1.52−2.46(14H,m),4.29(1H,m),5.33−5.51(2
H,m),6.28(1H,d,J=8.4Hz),7.70and7.83(each 2H,e
ach d,J=8.4Hz). IR(CHCl3):3439,3028,3012,2937,2871,2841,1739,170
8,1661,1620,1600,1513/cm. [α]D=+60.6゜(MeOH,c=1.01,22℃). No.2a−115 [α]D=+59.7゜(MeOH,c=0.99,24℃). No.2a−116 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.12and1.23(each 3H,each
s),1.52−2.46(14H,m),2.39(3H,s),4.27(1H,m),
5.33−5.51(2H,m),6.24(1H,d,J=9.0Hz),7.23and7.
62(each 2H,each d,J=8.4Hz). IR(CHCl3):3439,3028,3012,2937,2871,2841,1739,170
8,1661,1620,1600,1513/cm. [α]D=+59.7゜(MeOH,c=0.99,24℃). No.2a−117 [α]D=+56.7゜(MeOH,c=1.00,23℃). No.2a−118 CDCl3 300MHz 0.96(1H,d,J=10.2Hz),1.11and1.23(each 3H,each
s),1.53−2.44(14H,m),4.23(1H,m),5.34−5.51(2
H,m),6.02(2H,s),6.13(1H,d,J=8.7Hz),6.83(1H,
dd,J=1.2and7.8Hz),7.22−7.25(2H,m). IR(CHCl3):3453,3031,3020,3012,2924,2870,1740,170
8,1650,1619,1605,1519,1504,1480/cm. [α]D=+57.2゜(MeOH,c=1.02,23℃). No.2a−119 CDCl3 300MHz 0.96(1H,d,J=10.5Hz),1.07and1.23(each 3H,each
s),1.51−2.44(14H,m),2.32(3H,s),4.26(1H,m),
5.37−5.52(2H,m),6.40(1H,d,J=9.0Hz),7.09(1H,
m),7.30(1H,m),7.46(1H,m),7.66(1H,m). IR(CHCl3):3443,3028,3012,2925,2870,1766,1747,170
9,1657,1607,1516,1479/cm. [α]D=+53.2゜(MeOH,c=0.99,21℃). No.2a−120 CDCl3 300MHz 0.98(1H,d,J=10.2Hz),1.14and1.24(each 3H,each
s),1.53−2.44(14H,m),4.30(1H,m),5.35−5.52(2
H,m),6.42(1H,d,J=8.7Hz),6.85(1H,m),6.99(1H,
dd,J=1.2and8.4Hz),7.27(1H,m),7.39(1H,m). IR(CHCl3):3463,3033,3021,3014,2992,2924,2870,170
8,1643,1597,1523,1488/cm. [α]D=+46.3゜(MeOH,c=1.01,21℃). No.2a−121 CDCl3 300MHz 0.98(1H,d,J=10.2Hz),1.14and1.23(each 3H,each
s),1.47−2.47(14H,m),3.95(3H,s),4.31(1H,m),
5.32−5.50(2H,m),6.98(1H,dd,J=0.9and8.4Hz),7.
09(1H,ddd,J=0.9,7.7and8.4Hz),7.45(1H,m),8.19
(1H,dd,J=2.1and8.1Hz),8.32(1H,d,J=9.Hz). IR(CHCl3):3400,3078,3028,3020,3007,2924,2870,284
2,1736,1708,1640,1600,1536,1483,1470/cm. [α]D=+38.1゜(MeOH,c=1.02,23℃). No.2a−122 [α]D=+42.3゜(MeOH,c=0.99,23℃). No.2a−123 [α]D=+38.7゜(MeOH,c=1.00,21℃). No.2a−124 [α]D=+45.0゜(MeOH,c=1.01,21℃). m.p.119.0−120.0℃ No.2a−125 [α]D=+49.8゜(MeOH,c=1.01,22℃). No.2a−126 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.11and1.23(each 3H,each
s),1.52−2.47(14H,m),4.26(1H,m),5.34−5.50(2
H,m),6.22(1H,d,J=8.7Hz),7.55−7.61(4H,m). IR(CHCl3):3400,3078,3028,3020,3007,2924,2870,284
2,1736,1708,1640,1600,1536,1483,1470/cm. [α]D=+63.0゜(MeOH,c=1.01,23℃). No.2a−127 CDCl3 300MHz 0.91(1H,d,J=10.2Hz),1.10and1.20(each 3H,each
s),1.50−2.42(14H,m),4.23(1H,m),5.31−5.51(2
H,m),6.45(1H,d,J=8.4Hz),7.01(1H,d,J=7.4Hz),
7.22−7.27(2H,m),7.33−7.40(4H,m),7.53(2H,d,J
=9.0Hz),8.30and8.49(each 1H,each s). IR(CHCl3):3452,3028,3022,3015,2925,2870,1708,165
4,1590,1514,1478/cm. [α]D=+59.5゜(MeOH,c=1.01,23℃). No.2a−128 d6−DMSO 300MHz 0.84(1H,d,J=9.9Hz),1.06and1.19(each 3H,each
s),1.37−2.37(14H,m),3.79(1H,m),5.35−5.51(2
H,m),6.08(1H,d,J=8.7Hz),6.85−6.90(1H,m),7.1
8−7.23(2H,m),7.35−7.38(2H,m),8.42(1H,s),1
2.00(1H,s). IR(Nujol):3395,3345,2925,2866,2623,2506,1697,165
8,1638,1597,1557/cm. [α]D=+26.0゜(MeOH,c=1.01,23℃). m.p.164.0−166.0℃ No.2a−129 CDCl3 300MHz 1.01(1H,d,J=10.0Hz),1.17and1.25(each 3H,each
s),1.54−2.52(14H,m),4.34(1H,m),5.36−5.57(2
H,m),6.42(1H,d,J=8.6Hz),7.51−7.60(2H,m),7.7
7(1H,dd,J=1.8and8.6Hz),7.85−7.96(3H,m),8.24
(1H,bs). IR(CHCl3):3451,3060,3028,3010,2925,2870,1708,165
2,1629,1600,1517,1502/cm. [α]D=+68.6゜(MeOH,c=1.00,22℃) No.2a−130 CDCl3 300MHz 1.02(1H,d,J=10.2Hz),1.04and1.26(each 3H,each
s),1.54−2.52(14H,m),4.41(1H,m),5.41−5.58(2
H,m),6.14(1H,d,J=9.0Hz),7.43−7.59(4H,m),7.8
5−7.92(2H,m),8.27(1H,dd,J=1.8and7.2Hz). IR(CHCl3):3436,3032,3010,2924,2870,2664,1708,165
2,1512,1498/cm. [α]D=+93.9゜(MeOH,c=1.00,22℃). m.p.94.0−96.0℃ No.2a−131 [α]D=+50.2゜(MeOH,c=0.95,21℃). No.2a−132 [α]D=+10.9゜(MeOH,c=0.92,21℃). No.2a−133 [α]D=+60.4゜(MeOH,c=1.00,21℃). No.2a−134 [α]D=+38.5゜(MeOH,c=1.01,23℃). No.2a−135 [α]D=+52.5゜(MeOH,c=1.01,23℃). m.p.180.0−182.0℃ No.2a−136 [α]D=+35.3゜(MeOH,c=1.02,23℃). m.p.79.0−80.0℃ No.2a−137 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.11and1.22(each 3H,each
s),1.43(3H,t,J=6.9Hz),1.52−2.44(14H,m),4.03
(2H,q,J=9.6Hz),4.26(1H,m),5.33−5.50(2H,m),
6.19(1H,d,J=8.7Hz),6.88−7.00(6H,m),7.65−7.6
8(2H,m). IR(CHCl3):3455,3031,3024,3014,2988,2925,2870,174
1,1708,1649,1602,1521,1504,1490/cm. [α]D=+52.0゜(MeOH,c=1.01,23℃). No.2a−138 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.11and1.22(each 3H,each
s),1.35(6H,d,J=6.0Hz),1.53−2.46(14H,m),4.25
(1H,m),4.51(1H,m),5.33−5.50(2H,m),6.12(1H,
d,J=9.0Hz),6.87−6.99(6H,m),7.65−7.68(2H,
m). IR(CHCl3):3454,3031,3014,2980,2925,2870,1741,170
8,1649,1602,1522,1490/cm. [α]D=+50.0゜(MeOH,c=1.05,22℃). No.2a−139 CDCl3 300MHz 1.00(1H,d,J=10.2Hz),1.16and1.24(each 3H,each
s),1.59−2.52(14H,m),4.31(1H,m),5.40−5.53(2
H,m),6.36(1H,d,J=8.7Hz),6.70(1H,d,J=1.5Hz),
7.12(1H,m),7.30(1H,m),7.47(1H,dd,J=0.6and8.1
Hz),7.61(1H,d,J=8.4Hz). IR(CHCl3):3449,3243,3029,3022,3013,2925,2871,170
7,1631,1542,1505/cm. [α]D=+63.4゜(MeOH,c=1.00,23℃). m.p.178.0−179.0℃ No.2a−140 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.18and1.23(each 3H,each
s),1.57−2.50(14H,m),4.35(1H,m),5.32−5.55(2
H,m),6.42(1H,d,J=8.7Hz),6.70(1H,d,J=1.5Hz),
7.21−7.24(2H,m),,7.46(1H,m),7.76(1H,m),7.86
(1H,d,J=3.0Hz),10.20(1H,s). IR(CHCl3):3465,3010,2924,1739,1604,1546,1504/cm. [α]D=+39.4゜(MeOH,c=1.01,22℃). m.p.167.0−168.0℃ No.2a−141 CDCl3 300MHz 0.99(1H,d,J=10.2Hz),1.14and1.24(each 3H,each
s),1.55−2.44(14H,m),3.84(3H,s),4.27(1H,m),
5.34−5.52(2H,m),6.28(1H,d,J=9.0Hz),6.91and7.
47(each 2H,each d,J=9.0Hz),6.98and7.14(each 1
H,each d,J=16.5Hz),7.54and7.70(each 2H,eachd,J
=8.7Hz). IR(CHCl3):3453,3025,3015,2925,2870,2839,1740,170
8,1649,1602,1510,1493,1470/cm. [α]D=+73.4゜(MeOH,c=1.02,22℃). m.p.155.0−157.0℃ No.2a−142 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.11and1.23(each 3H,each
s),1.52−2.45(14H,m),3.79(3H,s),4.27(1H,m),
5.34−5.50(2H,m),6.24(1H,d,J=9.0Hz),6.49and6.
62(each 1H,each d,J=12.3Hz),6.77and7.16(each 2
H,each d,J=8.7Hz),7.32and7.59(each 2H,eachd,J=
8.1Hz). IR(CHCl3):3453,3025,3014,2925,2870,2839,1739,170
8,1649,1606,1510,1494/cm. [α]D=+60.7゜(MeOH,c=0.99,22℃). No.2a−143 [α]D=+57.3゜(MeOH,c=1.01,23℃). No.2a−144 [α]D=+12.2゜(MeOH,c=1.00,23℃). m.p.114.0−126.0℃ No.2a−145 CDCl3 300MHz 0.95(1H,d,J=10.2Hz),1.10and1.21(each 3H,each
s),1.52−2.44(14H,m),4.25(1H,m),5.33−5.49(2
H,m),6.37(1H,d,J=8.7Hz),7.45−7.47(3H,m),7.6
2−7.66(2H,m),7.69and7.80(each 2H,each d,J=7.5
Hz). IR(CHCl3):3449,3058,3027,3012,2925,2870,1708,165
5,1513,1481,1043/cm. [α]D=+61.0゜(MeOH,c=1.01,23℃). No.2a−146 CDCl3 300MHz 0.95(1H,d,J=10.5Hz),1.09and1.21(each 3H,each
s),1.50−2.41(14H,m),4.25(1H,m),5.33−5.49(2
H,m),6.33(1H,d,J=8.4Hz),7.49−7.61(3H,m),7.9
1−7.92(2H,m),7.82and7.97(each 2H,each d,J=8.7
Hz). IR(CHCl3):3447,3029,3023,3015,2925,2870,1708,166
0,1514,1484,1321,1161/cm. [α]D=+62.0゜(MeOH,c=1.00,22℃). No.2a−147 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.12and1.23(each 3H,each
s),1.52−2.46(14H,m),2.51(3H,s),4.26(1H,m),
5.34−5.51(2H,m),6.23(1H,d,J=8.4Hz),7.26and7.
64(each 2H,each d,J=8.4Hz). IR(CHCl3):3453,3027,3015,2925,2870,2665,1708,164
8,1596,1516,1484/cm. [α]D=+67.7゜(MeOH,c=0.82,22℃). No.2a−148 [α]D=+72.5゜(MeOH,c=1.01,25℃). No.2a−149 [α]D=+67.8゜(MeOH,c=0.98,25℃). No.2a−150 CDCl3 300MHz 0.94(1H,d,J=10.2Hz),1.10and1.23(each 3H,each
s),1.52−2.50(14H,m),4.22(1H,m),5.36−5.55(2
H,m),6.48(1H,d,J=8.4Hz),8.35(1H,s),8.90(1H,
s). IR(CHCl3):3443,3374,3091,3024,3012,2925,2871,170
9,1652,1525,1494/cm. [α]D=+58.1゜(MeOH,c=1.01,23℃). m.p.120.0−122.0℃ No.2a−151 [α]D=+40.6゜(MeOH,c=1.01,23℃). No.2a−152 CDCl3 300MHz 0.96(1H,d,J=10.5Hz),1.10and1.24(each 3H,each
s),1.50−2.50(14H,m),2.71(3H,s),4.26(1H,m),
5.37−5.51(2H,m),6.02(1H,d,J=9.0Hz),8.73(1H,
s). IR(CHCl3):3463,3435,3087,3025,3014,2925,2870,170
8,1649,1523,1503/cm. [α]D=+54.1゜(MeOH,c=1.02,22℃). No.2a−153 CDCl3 300MHz 0.95(1H,d,J=9.9Hz),1.11and1.23(each 3H,each
s),1.50−2.50(14H,m),2.50(3H,s),4.26(1H,m),
5.36−5.51(2H,m),6.01(1H,d,J=8.4Hz),6.88(1H,
d,J=5.1Hz),7.26(1H,d,J=5.1Hz). IR(CHCl3):3469,3431,3025,3013,2925,2871,2664,170
8,1639,1544,1505/cm. [α]D=+35.8゜(MeOH,c=1.03,22℃). No.2a−154 CDCl3 300MHz 0.95(1H,d,J=9.9Hz),1.10and1.22(each 3H,each
s),1.52−2.46(14H,m),2.51(3H,d,J=1.2Hz),4.26
(1H,m),5.34−5.50(2H,m),6.00(1H,d,J=8.4Hz),
6.73(1H,dd,J=5.1and3.6Hz),7.29(1H,d,J=3.6H
z). IR(CHCl3):3450,3431,3026,3011,2925,2869,1739,170
8,1639,1547,1508/cm. [α]D=+50.5゜(MeOH,c=1.01,22℃). No.2a−155 CDCl3 300MHz 0.99(1H,d,J=10.2Hz),1.19and1.25(each 3H,each
s),1.53−2.48(14H,m),4.31(1H,m),5.36−5.51(2
H,m),6.79(1H,d,J=9.3Hz),7.29(1H,m),7.41(1H,
m),7.48(1H,s),7.51(1H,m),7.66(1H,d,J=8.1H
z). IR(CHCl3):3436,3029,3024,3015,2925,2871,2670,170
8,1659,1598,1510/cm. [α]D=+69.1゜(MeOH,c=1.01,22℃). No.2a−156 CDCl3:CD3OD=10:1 300MHz 0.99(1H,d,J=9.9Hz),1.11and1.21(each 3H,each
s),1.56−2.58(14H,m),4.22(1H,m),5.35−5.59(2
H,m),6.83(1H,d,J=8.4Hz),7.48(1H,d,J=8.4Hz),
7.61(1H,dd,J=1.5and8.4Hz),8.09(1H,d,J=1.5H
z),8.12(1H,s). IR(KBr):3422,3115,2985,2922,2869,2609,1708,1636,
1578,1529,1470/cm. [α]D=+62.8゜(MeOH,c=1.01,22℃). No.2a−157 [α]D=+40.0゜(MeOH,c=0.95,22℃). No.2a−158 CDCl3 300MHz 1.00(1H,d,J=10.5Hz),1.17and1.24(each 3H,each
s),1.54−2.50(14H,m),4.34(1H,m),5.36−5.52(2
H,m),7.80(1H,d,J=9.0Hz),9.30(1H,s). IR(CHCl3):3410,3122,3030,3012,2925,2871,2668,170
9,1667,1538,1466/cm. [α]D=+44.9゜(MeOH,c=0.99,22℃). No.2a−159 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.13and1.22(each 3H,each
s),1.55−2.43(14H,m),3.03(6H,s),4.23(1H,m),
5.32−5.51(2H,m),6.16(1H,d,J=8.7Hz),6.87and7.
63(each 2H,each d,J=8.7Hz). IR(CHCl3):3457,3028,3006,2924,2870,2654,1739,170
9,1637,1608,1608,1534,1501/cm. [α]D=+64.8゜(MeOH,c=1.01,22℃). No.2a−160 d6−DMSO 300MHz 0.83(1H,d,J=9.9Hz),1.02and1.19(each 3H,each
s),1.38−1.61(3H,m),1.90−2.32(11H,m),3.90(1
H,m),5.41−5.44(2H,m),7.32(1H,dd,J=0.9and7.2H
z),7.45−7.60(2H,m),7.77(1H,dd,J=0.9and7.8H
z),8.03(1H,d,J=6.9Hz),12.40(1H,s). IR(Nujol):3315,2924,2856,2656,2535,1737,1703,163
7,1598,1581,1541/cm. [α]D=+78.5゜(MeOH,c=1.01,24℃). m.p.161.0−162.0℃ No.2a−161 [α]D=+65.3゜(MeOH,c=1.00,22℃). No.2a−162 CDCl3 300MHz 0.99(1H,d,J=10.2Hz),1.13and1.25(each 3H,each
s),1.53−2.45(14H,m),4.30(1H,m),5.36−5.51(2
H,m),6.32(1H,d,J=8.4Hz),7.88and8.28(each 2H,e
ach d,J=9.0Hz). IR(CHCl3):3448,3029,3016,2925,2870,1708,1664,160
2,1527,1484,1347/cm. [α]D=+72.7゜(MeOH,c=1.02,22℃). No.2a−163 CDCl3 300MHz 0.96(1H,d,J=10.2Hz),1.11and1.23(each 3H,each
s),1.55−2.51(14H,m),4.26(1H,m),5.36−5.57(2
H,m),6.68(1H,d,J=7.8Hz),7.41(1H,dd,J=4.8and
8.1Hz),8.20(1H,d,J=8.1Hz),8.66(1H,d,J=4.8H
z),9.00(1H,s). IR(CHCl3):3448,3026,3013,2925,2870,2534,1709,165
8,1590,1515,1471/cm. [α]D=+71.3゜(MeOH,c=1.01,22℃). No.2a−164 [α]D=+40.8゜(MeOH,c=0.98,22℃). No.2a−165 CDCl3 300MHz 0.96(1H,d,J=10.5Hz),1.11and1.24(each 3H,each
s),1.55−2.52(14H,m),4.24(1H,m),5.37−5.57(2
H,m),6.63(1H,d,J=7.8Hz),7.59and8.63(each 2H,e
ach d,J=6.0Hz). IR(CHCl3):3447,3346,3028,3016,2925,2870,2538,194
1,1708,1662,1556,1516/cm. [α]D=+75.4゜(MeOH,c=1.01,22℃). No.2a−166 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.11and1.22(each 3H,each
s),1.51−2.44(14H,m),2.95(6H,s),4.25(1H,m),
5.33−5.50(2H,m),6.19(1H,d,J=8.7Hz),6.77and6.
97(each 2H,each d,J=8.4Hz),6.94and7.65(each 2
H,each d,J=9.0Hz). IR(CHCl3):3453,3024,3016,2924,2871,2806,1739,170
8,1647,1612,1604,1515,1490/cm. [α]D=+53.1゜(MeOH,c=1.02,23℃). m.p.104.0−105.5℃ No.2a−167 CDCl3 300MHz 1.01(1H,d,J=9.9Hz),1.19and1.26(each 3H,each
s),1.56−2.53(14H,m),4.37(1H,m),5.35−5.55(2
H,m),6.47(1H,d,J=8.4Hz),7.61−7.71(2H,m),7.7
9(2H,s),7.89−7.97(2H,m),8.27(1H,d,J=2.1H
z),8.66−8.73(2H,m). IR(CHCl3):3450,3024,3014,2925,2870,2667,1707,165
0,1531,1509/cm. [α]D=+70.5゜(MeOH,c=1.00,22℃). No.2a−168 CDCl3 300MHz 1.02(1H,d,J=10.2Hz),1.20and1.26(each 3H,each
s),1.56−2.50(14H,m),4.38(1H,m),5.36−5.56(2
H,m),6.51(1H,d,J=8.4Hz),7.61−7.93(7H,m),8.7
4(1H,d,J=8.4Hz),9.15(1H,s). IR(CHCl3):3517,3451,3060,3028,3011,2925,2870,266
4,1709,1651,1519,1498/cm. [α]D=+54.4゜(MeOH,c=1.00,23℃). No.2a−169 CDCl3 300MHz 0.96(1H,d,J=10.5Hz),1.09and1.21(each 3H,each
s),1.50−2.44(14H,m),3.85(3H,s),4.24(1H,m),
5.32−5.48(2H,m),6.19(1H,d,J=8.4Hz),6.94and7.
45(each 2H,each d,J=9.0Hz),7.11and7.45(each 2
H,each d,J=8.7Hz). IR(CHCl3):3516,3453,3029,3009,2925,2870,2840,266
5,1708,1650,1593,1515,1493,1482/cm. [α]D=+57.8゜(MeOH,c=1.00,23℃). No.2a−170 CDCl3 300MHz 0.98(1H,d,J=10.2Hz),1.15and1.24(each 3H,each
s),1.52−2.50(14H,m),4.28(1H,m),5.33−5.54(2
H,m),6.25(1H,d,J=8.2Hz),7.38−7.44(2H,m),7.7
4(1H,s),7.81−7.86(2H,m). IR(CHCl3):3517,3448,3427,3024,3013,2925,2870,266
9,1708,1650,1562,1535,1500/cm. [α]D=+61.6゜(MeOH,c=1.00,23℃). No.2a−171 CDCl3 300MHz 0.96(1H,d,J=10.2Hz,1.11and1.22(each 3H,each
s),1.52−2.42(14H,m),2.48(3H,s),4.21(1H,m),
5.31−5.52(2H,m),6.06(1H,d,J=8.2Hz),6.97and7.
59(each 1H,each d,J=1.2Hz). IR(CHCl3):3452,3113,3028,3007,2925,2870,2669,170
8,1645,1554,1509/cm. [α]D=+52.4゜(MeOH,c=1.00,23℃). No.2a−172 CDCl3 300MHz 0.96(1H,d,J=10.2Hz),1.09and1.28(each 3H,each
s),1.50−2.40(14H,m),2.69(3H,s),4.24(1H,m),
5.35−5.51(2H,m),5.96(1H,d,J=8.7Hz),7.03and7.
07(each 1H,each d,J=5.4Hz). IR(CHCl3):3451,3031,3013,2925,2870,2666,1708,164
7,1542,1497/cm. [α]D=+51.2゜(MeOH,c=1.00,23℃). No.2a−173 CDCl3 300MHz 0.95(1H,d,J=10.2Hz),1.10and1.23(each 3H,each
s),1.50−2.45(14H,m),4.22(1H,m),5.35−5.49(2
H,m),6.05(1H,d,J=8.4Hz),7.26and7.75(each 1H,e
ach d,J=1.5Hz). IR(CHCl3):3451,3011,3029,3011,2925,2870,1708,165
2,1538,1500/cm. [α]D=+50.6゜(MeOH,c=1.01,23℃). No.2a−174 CDCl3 300MHz 0.96(1H,d,J=10.2Hz),1.13and1.23(each 3H,each
s),1.52−2.50(14H,m),4.29(1H,m),5.35−5.51(2
H,m),7.02(1H,d,J=8.4Hz),7.32and8.16(each 1H,e
ach d,J=3.9Hz). IR(CHCl3):3417,3115,3023,3014,2925,2870,1708,164
5,1530/cm. [α]D=+48.8゜(MeOH,c=1.02,23℃). No.2a−175 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.14and1.23(each 3H,each
s),1.50−2.52(14H,m),2.52(3H,s),4.29(1H,m),
5.34−5.51(2H,m),7.78(1H,d,J=9.0Hz),7.24and7.
52(each 1H,each d,J=5.4Hz). IR(CHCl3):3329,3093,3023,3015,2924,2871,1708,164
0,1526/cm. [α]D=+45.0゜(MeOH,c=1.01,23℃). No.2a−176 CDCl3 300MHz 0.95(1H,d,J=10.5Hz),1.09and1.23(each 3H,each
s),1.52−2.46(14H,m),2.40(3H,d,J=0.9Hz),4.24
(1H,m),5.35−5.51(2H,m),6.05(1H,d,J=8.7Hz),
6.95(1H,m),7.57(1H,d,J=3.3Hz). IR(CHCl3):3517,3444,3103,3024,3013,2926,2870,173
9,1708,1649,1636,1507/cm. [α]D=+54.8゜(MeOH,c=1.01,23℃). m.p.97.0−99.0℃ No.2a−177 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.11and1.23(each 3H,each
s),1.52−2.45(14H,m),3.93(3H,s),4.27(1H,m),
5.34−5.50(2H,m),6.35(1H,d,J=3.3Hz),7.80(1H,
d,J=8.7Hz),8.10(1H,d,J=3.3Hz). IR(CHCl3):3395,3121,3031,3019,3012,2925,2871,173
9,1709,1640,1557,1533/cm. [α]D=+22.8゜(MeOH,c=1.01,23℃). m.p.109.0−112.0℃ No.2a−178 CDCl3 300MHz 0.96(1H,d,J=10.5Hz),1.10and1.23(each 3H,each
s),1.51−2.45(14H,m),4.24(1H,m),5.35−5.50(2
H,m),6.09(1H,d,J=8.4Hz),7.17−7.31(6H,m),7.9
5(1H,d,J=1.5Hz). IR(CHCl3):3510,3451,3062,3031,3022,3011,2925,287
0,2662,1708,1651,1582,15351497,1477/cm. [α]D=+47.9゜(MeOH,c=1.01,25℃). No.2a−179 CDCl3 300MHz 0.96(1H,d,J=10.2Hz),1.14and1.24(each 3H,each
s),1.52−2.48(14H,m),4.30(1H,m),5.36−5.52(2
H,m),6.73(1H,d,J=9.0Hz),6.26and7.37(each 1H,e
ach d,J=6.0Hz). IR(CHCl3):3509,3429,3115,3094,3025,3014,2925,287
1,2666,1708,1649,1529,1510/cm. [α]D=+51.0゜(MeOH,c=1.02,25℃). No.2a−180 CDCl3 300MHz 0.95(1H,d,J=10.2Hz),1.14and1.24(each 3H,each
s),1.52−2.46(14H,m),3.89(3H,s),4.21(1H,m),
5.35−5.50(2H,m),6.05(1H,d,J=8.4Hz),6.46and7.
04(each 1H,each d,J=1.8Hz). IR(CHCl3):3516,3450,3114,3031,3010,2925,2871,170
8,1648,1546,1511,1477/cm. [α]D=+49.1゜(MeOH,c=1.01,25℃). No.2a−181 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.14and1.23(each 3H,each
s),1.52−2.48(14H,m),2.42(3H,s),4.31(1H,m),
5.34−5.52(2H,m),8.07(1H,d,J=9.3Hz),7.27and8.
17(each 1H,each d,J=3.3Hz). IR(CHCl3):3510,3301,3112,3023,3007,2924,2871,266
3,1708,1636,1534/cm. [α]D=+41.0゜(MeOH,c=0.96,25℃). No.2a−182 CDCl3 300MHz 0.96(1H,d,J=10.2Hz),1.11and1.23(each 3H,each
s),1.53−2.46(14H,m),2.51(3H,s),4.21(1H,m),
5.35−5.51(2H,m),6.05(1H,d,J=8.1Hz),7.26and7.
78(each 1H,each d,J=1.8Hz). IR(CHCl3):3509,3450,3109,3024,3012,2925,2870,266
6,1708,1650,1535,1498,1471/cm. [α]D=+52.9゜(MeOH,c=0.95,25℃). No.2a−183 CDCl3 300MHz 0.96(1H,d,J=10.5Hz),1.12and1.22(each 3H,each
s),1.52−2.46(14H,m),4.25(1H,m),5.33−5.51(2
H,m),6.17(1H,d,J=8.7Hz),7.01−7.05(3H,m),7.1
4and7.62(each 2H,each d,J=8.7Hz),7.27−7.34(2
H,m). IR(CHCl3):3428,3026,3015,2925,2870,2666,1739,170
8,1643,1613,1594,1526,1499/cm. [α]D=+64.8゜(MeOH,c=1.02,23℃). No.2a−184 CDCl3 300MHz 1.01(1H,d,J=10.2Hz),1.18and1.26(each 3H,each
s),1.55−2.50(14H,m),4.35(1H,m),5.35−5.55(2
H,m),6.42(1H,t,J=8.7Hz),7.46−7.52(2H,m),7.7
3(1H,dd,J=1.8and8.4Hz),7.83−7.89(2H,m),8.21
(1H,m),8.59(1H,d,J=1.5Hz). IR(CHCl3):3451,3031,3014,2925,2870,2660,1739,170
8,1650,1604,1513,1463/cm. [α]D=+58.3゜(MeOH,c=1.00,23℃). No.2a−185 CDCl3 300MHz 1.00(1H,d,J=10.2Hz),1.18and1.25(each 3H,each
s),1.55−2.50(14H,m),4.34(1H,m),5.35−5.54(2
H,m),6.36(1H,d,J=8.7Hz),7.37(1H,d,J=7.4Hz),
7.50(1H,m),7.57−7.59(2H,m),7.79(1H,dd,J=1.8
and8.1Hz),7.99(1H,d,J=7.8Hz),8.39(1H,d,J=1.8
Hz). IR(CHCl3):3451,3030,3020,2870,2665,1708,1652,163
2,1603,1586,1514,1469,1448/cm. [α]D=+59.4゜(MeOH,c=1.01,24℃). No.2a−186 CDCl3 300MHz 1.00(1H,d,J=10.5Hz),1.17and1.25(each 3H,each
s),1.54−2.50(14H,m),4.33(1H,m),5.35−5.54(2
H,m),6.37(1H,d,J=8.7Hz),7.37(1H,d,J=7.4Hz),
7.51(1H,d,J=7.8Hz),7.56(1H,m),7.70(1H,dd,J=
1.2and8.4Hz),7.97(3H,m). IR(CHCl3):3451,3030,3014,2924,2870,2671,1739,170
8,1652,1577,1517,1488,1471/cm. [α]D=+72.2゜(MeOH,c=1.00,24℃). No.2a−187 CDCl3 300MHz 1.00(1H,d,J=9.8Hz),1.18and1.25(each 3H,each
s),1.54−2.53(14H,m),4.07(3H,s),4.37(1H,m),
5.30−5.54(2H,m),7.34(1H,m),7.47(1H,s),7.47
−7.60(2H,m),7.93(1H,d,J=7.8Hz),8.43(1H,s),
8.49(1H,d,J=9.0Hz). IR(CHCl3):3397,3074,3027,3020,3009,2924,1738,170
8,1647,1633,1534,1465,1453/cm. [α]D=+43.7゜(MeOH,c=1.01,25℃). No.2a−188 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.11and1.23(each 3H,each
s),1.53−2.50(14H,m),4.23(1H,m),5.37−5.50(2
H,m),6.10(1H,d,J=9.0Hz),6.20(1H,m),6.51(1H,
m),6.97(1H,m),10.81(1H,bs). IR(CHCl3):3450,3236,3112,3029,3015,2925,2871,264
5,1701,1616,1558,1516/cm. [α]D=+50.6゜(MeOH,c=1.01,24℃). No.2a−189 CDCl3 300MHz 0.94(1H,d,J=9.9Hz),1.11and1.23(each 3H,each
s),1.50−2.46(14H,m),3.93(3H,s),4.18(1H,m),
5.35−5.52(2H,m),6.03(1H,d,J=9.3Hz),6.09(1H,
m),6.48(1H,m),6.73(1H,m). IR(CHCl3):3452,3102,3028,3007,2925,2871,2666,173
9,1708,1650,1536,1499,1471/cm. [α]D=+49.8゜(MeOH,c=1.01,23℃). m.p.101.5−103.5℃ No.2a−190 CDCl3 300MHz 0.94(1H,d,J=10.2Hz),1.11and1.21(each 3H,each
s),1.54−2.47(14H,m),4.23(1H,m),5.33−5.52(2
H,m),6.06(1H,d,J=9.0Hz),6.34(1H,m),6.75(1H,
m),6.36(1H,m),9.71(1H,bs). IR(CHCl3):3470,3215,3030,3020,3010,2925,2871,266
4,1709,1613,1564,1510/cm. [α]D=+43.3゜(MeOH,c=1.01,24℃). No.2a−191 CDCl3 300MHz 0.96(1H,d,J=10.2Hz),1.11and1.22(each 3H,each
s),1.55−2.44(14H,m),3.66(3H,s),4.20(1H,m),
5.35−5.51(2H,m),5.93(1H,d,J=8.4Hz),6.27(1H,
dd,J=1.8and2.7Hz),6.56(1H,d,J=2.7Hz),7.19(1
H,d,J=1.8Hz). IR(CHCl3):3452,3031,3018,3006,2925,2871,2662,173
6,1710,1634,1609,1556,1498/cm. [α]D=+43.1゜(MeOH,c=1.01,23℃). No.2a−192 CDCl3 300MHz 0.96(1H,d,J=10.5Hz),1.11and1.21(each 3H,each
s),1.43(3H,t,J=7.5Hz),1.54−2.44(14H,m),3.93
(1H,q,J=7.5Hz),4.21(1H,m),5.33−5.51(2H,m),
5.94(1H,d,J=8.4Hz),6.27(1H,dd,J=1.8and2.7H
z),6.62(1H,d,J=2.7Hz),7.26(1H,t,J=1.8Hz). IR(CHCl3):3630,3452,3032,3018,3006,2925,2871,266
1,1735,1710,1633,1610,1555,1497/cm. [α]D=+40.1゜(MeOH,c=1.00,23℃). No.2a−193 CDCl3 300MHz 0.95(1H,d,J=10.2Hz),1.10and1.22(each 3H,each
s),1.53−2.49(14H,m),2.58(3H,s),4.21(1H,m),
5.35−5.54(2H,m),6.15(1H,d,J=8.1Hz),6.52(1H,
dd,J=1.8and3.6Hz),7.29(1H,t,J=3.6Hz),7.94(1
H,t,J=1.8Hz). IR(CHCl3):3516,3450,3410,3152,3027,3015,2925,287
1,2670,1732,1648,1574,1509/cm. [α]D=+45.0゜(MeOH,c=1.01,25℃). No.2a−194 CDCl3 300MHz 0.99(1H,d,J=10.2Hz),1.11and1.24(each 3H,each
s),1.52−2.53(14H,m),4.34(1H,m),5.33−5.57(2
H,m),6.21(1H,d,J=8.6Hz),7.35−7.50(2H,m),7.8
3(1H,s),7.86(1H,m),8.31(1H,m). IR(CHCl3):3443,3067,3013,2925,2870,2665,1708,165
1,1515,1493/cm. [α]D=+55.7゜(MeOH,c=1.01,23℃). No.2a−195 CDCl3 300MHz 1.01(1H,d,J=10.0Hz),1.06and1.26(each 3H,each
s),1.50−2.64(14H,m),2.68(3H,s),4.40(1H,m),
5.36−5.61(2H,m),6.02(1H,d,J=9.4Hz),7.30−7.4
2(2H,m),7.73−7.86(2H,m). IR(CHCl3):3510,3434,3062,3029,3014,2924,2871,266
9,1708,1650,1563,1539,1500/cm. [α]D=+72.4゜(MeOH,c=1.00,23℃). m.p.111.0−112.0℃ No.2a−196 CDCl3 300MHz 0.42and1.04(each 3H,each s),0.80(1H,d,J=10.0H
z),1.11−2.48(14H,m),2.24(3H,s),4.02(1H,m),
5.23−5.44(2H,m),5.53(1H,d,J=8.8Hz),7.27−7.3
1(2H,m),7.42−7.48(3H,m),7.93(1H,s). IR(CHCl3):3419,3114,3025,3006,2924,2871,2662,173
7,1709,1636,1540,1519/cm. [α]D=+43.7゜(MeOH,c=1.01,23℃). No.2a−197 CDCl3 300MHz 0.95(1H,d,J=10.0Hz),1.09and1.23(each 3H,each
s),1.54−2.46(18H,m),2.77(4H,bs),4.21(1H,
m),5.32−5.54(2H,m),6.02(1H,d,J=8.6Hz),7.43
(1H,s). IR(CHCl3):3445,3101,3024,3014,2928,2865,2661,173
9,1708,1646,1550,1507/cm. [α]D=+51.9゜(MeOH,c=1.01,23℃). No.2a−198 CDCl3 300MHz 0.96(1H,d,J=10.2Hz),1.11and1.22(each 3H,each
s),1.50−2.44(14H,m),4.24(1H,m),4.42(2H,s),
5.35−5.49(2H,m),6.25(1H,d,J=8.1Hz),7.33(1H,
m),7.43(1H,dd,J=1.5and7.5Hz),7.49(1H,d,J=8.1
Hz),7.60−7.63(1H,m),7.68(1H,dd,J=1.8and7.8H
z),8.02(1H,d,J=1.8Hz),8.19(1H,dd,J=1.5and8.1
Hz). IR(CHCl3):3448,3030,3012,2925,2870,1739,1708,167
1,1588,1559,1514,1472/cm. [α]D=+56.9゜(MeOH,c=1.01,24℃). No.2a−199 CDCl3 300MHz 0.96(1H,d,J=10.2Hz),1.11and1.22(each 3H,each
s),1.51−2.46(14H,m),3.40(1H,m),3.76(1H,m),
4.24(1H,m),5.33−5.51(2H,m),6.25(1H,m),7.16
(1H,m),7.24−7.33(2H,m),7.46(1H,d,J=7.5Hz),
7.52−7.60(2H,m),7.85(1H,dd,J=1.8and4.5Hz). IR(CHCl3):3583,3447,3062,3028,3013,2924,2871,266
3,1708,1651,1600,1557,1514,1471/cm. [α]D=+54.8゜(MeOH,c=1.00,23℃). No.2a−200 CDCl3 300MHz 0.96(1H,d,J=10.2Hz),1.12and1.23(each 3H,each
s),1.51−2.46(14H,m),4.25(1H,m),5.34−5.51(2
H,m),6.25(1H,d,J=8.4Hz),7.02and7.10(each 1H,e
ach d,J=12.3Hz)7.23−7.33(4H,m),7.50(1H,m),
7.64(1H,dd,J=1.8and7.8Hz),7.82(1H,d,J=1.8H
z). IR(CHCl3):3450,3060,3025,3014,2925,2871,2662,170
8,1653,1596,1542,1513,1473/cm. [α]D=+62.5゜(MeOH,c=1.00,24℃). No.2a−201 CDCl3 300MHz 0.95(1H,d,J=9.9Hz),1.15and1.22(each 3H,each
s),1.55−2.60(14H,m),4.26(1H,m),5.35−5.63(2
H,m),7.14(1H,d,J=9.9Hz),7.34and7.40(each 1H,e
ach d,J=1.29Hz),7.62−7.73(4H,m),8.25−8.30(2
H,m),8.72(1H,d,J=1.5Hz). IR(CHCl3):3443,3389,3297,3061,3030,3016,2925,287
0,1726,1708,1652,1603,1521,1483,1472,1309/cm. [α]D=+61.1゜(MeOH,c=1.01,23℃). No.2a−202 CDCl3 300MHz 0.96(1H,d,J=10.2Hz),1.09and1.22(each 3H,each
s),1.52−2.43(14H,m),2.63(3H,s),4.25(1H,m),
5.33−5.49(2H,m),6.19(1H,d,J=8.4Hz),7.10and7.
58(each 2H,each d,J=9.0Hz),7.21(1H,m),7.30−
7.32(2H,m),7.46(1H,d,J=7.5Hz). IR(CHCl3):3511,3453,3062,3032,3014,2925,2870,173
9,1708,1650,1595,1556,1516,1482,1471/cm. [α]D=+60.2゜(MeOH,c=1.01,25℃). No.2a−203 CDCl3 300MHz 0.96(1H,d,J=10.5Hz),1.09and1.23(each 3H,each
s),1.52−2.43(14H,m),4.23(1H,m),5.35−5.51(2
H,m),5.93(1H,d,J=8.7Hz),6.56(1H,dd,J=0.9and
1.8Hz),7.43(1H,t,J=1.8Hz),7.92(1H,dd,J=0.9an
d1.8Hz). IR(CHCl3):3517,3450,3134,3031,3008,2925,2870,266
7,1708,1656,1588,1570,1514/cm. [α]D=+46.7゜(MeOH,c=0.92,25℃). No.2b−1 [α]D=+25.6゜(MeOH,c=1.01,23℃). No.2b−2 [α]D=+38.9゜(MeOH,c=1.01,24℃). No.2c−1 [α]D=+60.5゜(MeOH,c=1.01,22℃). No.2c−2 [α]D=+55.8゜(MeOH,c=0.92,22℃). No.2c−3 [α]D=+54.7゜(MeOH,c=1.01,22℃). No.2d−1 [α]D=−6.2゜(MeOH,c=1.00,21℃). No.2d−2 [α]D=+15.8゜(MeOH,c=0.34,22℃). No.2d−3 [α]D=+31.6゜(MeOH,c=1.01,22℃). No.2e−1 [α]D=−9.4゜(MeOH,c=1.00,22℃). No.2e−2 [α]D=−1.8゜(MeOH,c=1.02,23℃). No.2e−3 [α]D=−6.7゜(MeOH,c=1.01,23℃). No.2f−1 [α]D=+6.8゜(MeOH,c=1.01,23℃). No.2f−2 [α]D=−2.6゜(MeOH,c=1.00,22℃). No.2f−3 [α]D=−3.5゜(MeOH,c=1.01,22℃). No.2g−1 [α]D=+54.6゜(MeOH,c=1.01,24℃). No.3a−2 CDCl3 300MHz 0.98−2.15(14H,m),2.31(2H,t,J=7.2Hz),2.35−2.
40(1H,m),3.10−3.20(1H,m),5.00(1H,d,J=6.9H
z),5.30−5.48(2H,m),6.75(1H,d,J=10.2Hz),7.38
−7.52(6H,m). IR(CDCl3):3266,3028,2954,2874,1709,1620,1448,141
2,1318,1141,970,892/cm. [α]D=+20.3±0.6゜(CHCl3,c=1.05,24℃). No.3a−3 CDCl3 300MHz 0.95−2.00(14H,m),2.20−2.29)(3H,m),3.00−3.0
8(1H,m),3.66−(3H,s),5.00(1H,d,J=6.6Hz),5.1
3−5.29(2H,m),7.38−7.52(3H,m),7.59−7.65(2H,
m).7.69−7.75(2H,m),7.92−7.98(2H,m). IR(CHCl3):3376,3018,2946,2868,1727,1594,1436,139
5,1322,1157,1095,890/cm. [α]D=+2.3±0.4゜(CHCl3,c=1.03,22℃). mp.65−66.5℃ No.3a−4 CDCl3 300MHz 0.93−2.05(14H,m),2.15−2.22(1H,m),2.31(2H,t,
J=7.2Hz),3.01−3.10(1H,m),5.18−5.31(3H,m),
7.38−7.52(3H,m),7.58−7.66(2H,m),7.69−7.76
(2H,m),7.92−7.98(2H,m) IR(CHCl3):3374,3260,3020,2948,2868,1708,1594,147
9,1396,1319,1156,1095,1052,891/cm. [α]D=+13.1±0.5゜(CHCl3,c=1.16,24℃). No.3a−6 CD3OD 300MHz 1.04−1.95(14H,m),2.07(2H,t,J=7.8Hz),2.14−2.
22(1H,m),2.94−3.00(1H,m),5.04−5.25(2H,m),
7.36−7.52(3H,m),7.66−7.71(2H,m),7.78−7.85
(2H,m),7.91−7.97(2H,m). IR(KBr):3421,3278,2951,2872,1562,1481,1409,1317,
1156,1097,1057,895/cm. [α]D=−15.3±0.5゜(CHCl3,c=1.06,23℃). mp.105−112℃ No.3a−11 CDCl3 300MHz 0.90−2.04(14H,m),2.08−2.19(1H,m),2.35(2H,t,
J=7.2Hz),2.95−3.04(1H,m),5.17−5.32(3H,m),
7.56−7.63(2H,m),7.83−7.95(2H,m). IR(CHCl3):3260,3020,2948,2868,1707,1569,1456,138
3,1325,1268,1160,1088,1053,1006,892/cm. [α]D=+8.3±0.5゜(CHCl3,c=1.00,22℃). No.3a−16 CDCl3 300MHz 0.80−1.90(14H,m),1.98−2.04(1H,m),2.27(2H,t,
J=7.2Hz),2.88(6H,s),2.90−2.98(1H,m),4.88−
5.00(2H,m),5.13(1H,d,J=7.2Hz),7.18(1H,d,J=
7.5Hz),7.48−7.60(2H,m),8.25−8.33(2H,m),8.53
(1H,d,J=8.7Hz). IR(CHCl3):3272,3020,2946,2866,2782,1708,1573,145
5,1407,1311,1229,1160,1142,1070,942,891/cm. [α]D=−19.7±0.6゜(CHCl3,c=1.08,23.5℃). No.3a−31 CDCl3 300MHz 0.80−1.85(14H,m),2.02−2.08(1H,m),2.20(2H,t,
J=7.2Hz),2.85−2.95(1H,m),3.68(3H,s),4.80−
4.92(2H,m),4.96(1H,d,J=6.9Hz),7.50−7.70(3H,
m),7.92−7.98(1H,m),8.07(1H,d,J=8.4Hz),8.29
(1H,dd,J=1.5&7.5Hz),8.65(1H,d,J=8.7Hz). IR(CHCl3):3374,3016,2946,2868,1727,1506,1435,131
8,1160,1133,1105,1051,984,890/cm. [α]D=−39.3±0.8゜(CHCl3,c=1.07,22℃). No.3a−32 CDCl3 300MHz 0.80−1.90(14H,m),1.95−2.05(1H,m),2.27(2H,t,
J=7.2Hz),2.90−2.96(1H,m),4.85−5.00(2H,m),
5.23(1H,d,J=6.6Hz),7.50−7.72(3H,m),7.95(1H,
d,J=8.1Hz),8.07(1H,d,J=8.4Hz),8.29(1H,dd,J=
1.2&7.5Hz),8.66(1H,d,J=9.0Hz). IR(CHCl3):3270,3020,2948,2868,1708,1455,1412,131
7,1159,1132,1104,1079,1051,983,891/cm. [α]D=−29.2±0.6゜(CHCl3,c=1.08,22℃). No.3a−33 CD3OD 300MHz 0.94−1.84(14H,m),1.96−2.08(3H,m),2.77−2.84
(1H,m),4.67−4.84(2H,m),7.55−7.75(3H,m),8.0
2(1H,d,J=7.8Hz),8.12−8.26(2H,m),8.74(1H,d,J
=8.7Hz). IR(KBr):3432,3298,2951,2872,1564,1412,1315,1159,
1134,1107,1082,1058,986/cm. [α]D=−79.9±1.2゜(CH3OH,c=1.00,23℃). No.3a−34 CDCl3 300MHz 0.97−1.91(14H,m),2.13−2.20(1H,m),2.42(2H,t,
J=7.2Hz),3.00−3.07(1H,m),5.06−5.24(2H,m),
5.33(1H,d,J=6.9Hz),7.57−7.68(2H,m),7.82−8.0
0(4H,m),8.45(1H,d,J=1.2Hz) IR(CHCl3):3260,3020,2948,1708,1408,1319,1154,112
9,1073,953,893/cm. [α]D=+20.7±0.6゜(CHCl3,c=1.07,22℃). No.3a−35 CD3OD 300MHz 1.03−2.20(m,17H),2.97(m,1H),5.02(m,2H),7.64
(m,2H),8.00(m,4H),8.43(S,1H). IR(KBr):3360,3285,1562,1407,1316,1153,1130,1075/
cm. [α]D=≒0 [α]365=+20.9±0.6゜(CH3OH,c=1.04,23℃). No.3d−1 CDCl3 300MHz 0.93−2.55(m,17H),3.02(m,1H),5.24(m,2H),6.48
(m,1H),7.35−7.60(m,3H),7.85−8.00(m,2H) IR(Nujol):3275,1548,1160,1094,758,719,689,591,55
7/cm. [α]D=+19.0±0.6゜(CH3OH,c=1.010,26.5℃). 元素分析(C20H26NO4S.1/2Ca・1.0H2Oとして) 計算値:C.57,94;H,6.82;N,3.38;Ca,4.83;H2O,4.35 実測値:C.57,80;H,6.68;N,3.68;Ca,5.06;H2O,4.50 No.3d−6 [α]D=−20.7±0.6゜(CHCl3,c=1.00,24℃). No.3d−7 [α]D=−32±0.4゜(CHCl3,c=1.03,22℃). mp.65−67℃ No.3d−8 [α]D=−14.5±0.5゜(CHCl3,c=1.07,24℃). No.3d−9 [α]D=−12.2±0.5゜(CH3OH,c=1.00,23℃). mp.119−125℃ No.3d−10 [α]D=+39.7±0.8゜(CHCl3,c=1.07,22℃). No.3d−11 [α]D=+29.2±0.7゜(CHCl3,c=1.06,22℃). No.3d−12 [α]D=+76.4±1.1゜(CH3OH,c=1.03,24℃). No.3d−14 [α]D=−20.6±0.6゜(CHCl3,c=1.07,22℃). No.3d−15 [α]365=−28.0±0.7゜(CH3OH,c=1.03,24.5℃). No.3d−16 [α]D=−8.7±0.5゜(CHCl3,c=1.06,22℃). No.3d−17 CDCl3 300MHz 0.80−2.15(m,24H),2.32(t,J=7Hz,2H),2.68(t,J
=7Hz,2H),3.02(m,1H),2.15(m,24H),2.32(t,J=7
Hz,2H),2.68(t,J=7Hz,2H),3.02(m,1H),5.22(m,2
H),5.38(d,J=7Hz,1H),7.30(A2B2q−Apart,J=8Hz,
2H),7.81(A2B2qBpart,J=8Hz,2H),9.86(br.s,1
H). [α]D=≒0 [α]365=−9.7±0.5゜(CHCl3,c=1.03,22℃). No.3d−24 [α]D=+19.2±0.6゜(CHCl3,c=1.05,23℃). No.3d−26 CD3OD 300MHz 0.90−2.20(20H,m),2.88(1H,m),3.07(2H,q,J=7.0
Hz),5.00−5.40(2H,m),7.20−7.60(4H,m),7.95(1
H,m). IR(KBr):3415,3254,1698,1564,1314,1154/cm. No.3d−28 CD3OD 300MHz 0.90−2.20(20H,m),2.73(1H,q,J=7.0Hz),2.93(1
H,m),5.00−5.30(2H,m),7.40−7.50(2H,m),7.60−
7.77(2H,m). IR(KBr):3435,3280,1562,1323,1304,1151/cm. No.3d−30 元素分析C20H25BrNO4SNa Calc.C50.21;H5.27;Br16.70;N2.93;S6.70;Na4.81 found.C50.22;H5.40;Br15.57;N2.88;S6.41;Na5.10 IR(KBr):3425,3280,3085,1697,1570,1410,1321,1165,
1155/cm. No.3e−1 CD3OD 300MHz 0.71(1H,d,J=10.2Hz),1.04(3H,s),1.12(3H,s),
1.35−2.28(14H,m),2.24(3H,s),3.17−3.25(1H,
m),5.18−5.39(2H,m),7.37(2H,d,J=8.4Hz),7.75
(2H,d,J=8.4Hz). IR(CHCl3):3400,3289,2986,2924,2870,1559,1424,132
2,1305,1160,1095,1075,1030/cm. [α]D=+25.9±0.7゜(CH3OH,c=1.00,23℃). 上記実施例で得た化合物につき、以下の実験例に示す
方法で、インビボ及びインビトロ活性を試験した。
50,1608,1580(w),1523,1501,1482/cm. [α]D=+59゜(CHCl3,c=1.49,25℃) No.1m−4 CDCl3 300MHz 1.08−2.25(14H,m),2.36(2H,t,J=7.4Hz),2.59(1
H,m),3.91(1H,m),5.28−5.48(3H,m),6.29(1H,d,J
=7.4Hz),7.38−7.50(3H,m),7.61−7.67(4H,m),7.
81−7.86(2H,m). IR(CHCl3):3436,3010,2948,2868,1727,1715(sh)164
9,1615(w),1524,1502,1482,1372/cm. [α]D=+72゜(CHCl3,c=0.98,25℃) No.1m−5 CDCl3 300MHz 1.09−2.20(14H,m),2.32(2H,t,J=7.2Hz),2.63(1
H,m),3.63(3H,s),3.92(1H,m),5.31−5.51(2H,
m),6.35(1H,d,J=7.0Hz),7.51−7.60(3H,m),7.92
−7.97(6H,m). IR(CHCl3):3436,3008,2946,2875,1727,1652,1608
(w),1515,1484/cm. [α]D=+82゜(CHCl3,c=0.99,25℃) No.1m−6 CDCl3 300MHz 1.09−2.23(14H,m),2.37(2H,t,J=7.2Hz),2.60(1
H,m),3.92(1H,m),5.30−5.49(2H,m),6.32(1H,d,J
=7.4Hz),7.51−7.55(3H,m),7.85−7.98(6H,m). IR(CHCl3):3436,3010,2950,2875,2670,1727,1715(s
h)1650,1605(w),1515,1484/cm. [α]D=+84゜(CHCl3,c=1.54,25℃) No.1m−7 CDCl3 300MHz 1.03−2.18(14H,m),2.32(2H,t,J=7.4Hz),2.59(1
H,m),3.64(3H,s),3.89(1H,m),5.29−5.49(2H,
m),6.16(1H,d,J=7.8Hz),6.98−7.06(4H,m),7.14
−7.20(1H,m),7.34−7.41(2H,m),7.73−7.78(2H,
m). IR(CHCl3):3438,3008,2946,2868,1727,1648,1610,158
6,1519,1485/cm. [α]D=+54゜(CHCl3,c=1.29,25℃). No.1m−8 CDCl3 300MHz 1.06−2.21(14H,m),2.36(2H,t,J=7.5Hz),2.58(1
H,m),3.88(1H,m),5.31−5.46(2H,m),6.17(1H,d,J
=6.9Hz),6.99−7.05(4H,m),7.15−7.21(1H,m),7.
36−7.41(2H,m),7.72−7.75(2H,m). IR(CHCl3):3436,3010,2948,2868,2675,1730(sh),17
09,1647,1608,1586,1520,1485/cm. [α]D=+56゜(CHCl3,c=0.97,25℃) No.1m−9 CDCl3 300MHz 1.05−2.18(14H,m),2.29−2.34(5H,m),2.59(1H,
m),3.64(3H,s),3.89(1H,m),5.32−5.46(2H,m),
6.16(1H,d,J=7.5Hz),7.00−7.11(6H,m),7.74−7.7
7(2H,m). IR(CHCl3):3440,3010,2946,2868,1729,1649,1595,151
9,1488/cm. [α]D=+47゜(CHCl3,c=0.82,25℃). No.1m−10 CDCl3 300MHz 1.04−2.20(14H,m),2.31−2.39(5H,m),2.57(1H,
m),3.87(1H,m),5.28−5.47(2H,m),6.17(1H,d,J=
7.0Hz),6.99−7.12(6H,m),7.72−7.76(2H,m). IR(CHCl3):3674,3572,3438,3010,2948,2868,2626,174
8,1710,1648,1615,1595,1520,1489/cm. [α]D=+51゜(CHCl3,c=0.91,25℃) No.1m−11 CDCl3 300MHz 1.04−2.16(14H,m),2.31(2H,t,J=7.2Hz),2.59(1
H,m),3.63(3H,s),3.89(1H,m),5.29−5.49(2H,
m),6.24(1H,d,J=7.4Hz),6.54(1H,s),6.83−6.93
(6H,m),7.69−7.73(2H,m). IR(CHCl3):3674,3588,3438,3296,3010,2946,2868,172
5,1646,1603,1520,1504,1489/cm. [α]D=+51゜(CHCl3,c=0.91,25℃) No.1m−12 CDCl3 300MHz 1.04−2.21(14H,m),2.33(2H,t,J=8.0Hz),2.56(1
H,m),3.87(1H,m),5.28−5.48(2H,m),6.23(1H,d,J
=8.0Hz),6.75(1H,m),6.87−6.94(6H,m),7.66−7.
71(2H,m),9.63(1H,bs). IR(CHCl3):3674,3582,3436,3275,3010,2950,2868,267
5,1727,1710(sh),1643,1603,1522,1504,1490/cm. [α]D=+30゜(CHCl3,c=0.97,25℃) No.1m−13 CDCl3 300MHz 1.01−2.18(14H,m),2.31(2H,t,J=7.4Hz),2.58(1
H,m),3.63(3H,s),3.82(3H,s),3.89(1H,m),5.29
−5.48(2H,m),6.14(1H,d,J=7.0Hz),6.88−7.02(6
H,m),7.70−7.74(2H,m). IR(CHCl3):3442,3402,3004,2946,2868,1727,1648,160
0,1518,1499/cm. [α]D=+42゜(CHCl3,c=1.82,26℃) No.1m−14 CDCl3 300MHz 1.05−2.21(14H,m),2.35(2H,t,J=7.2Hz),2.55(1
H,m),3.82(3H,s),3.88(1H,m),5.27−5.46(2H,
m),6.16(1H,d,J=7.2Hz),6.88−7.02(6H,m),7.68
−7.73(2H,m). IR(CHCl3):3438,3012,2948,2870,2650,1730(sh),17
09,1647,1615(sh)1601,1519,1492/cm. [α]D=+64゜(CHCl3,c=0.70,25℃) No.1m−15 CDCl3 300MHz 1.05−2.20(14H,m),2.29−2.36(5H,m),2.62(1H,
m),3.63(3H,s),3.92(1H,m),5.30−5.50(2H,m),
6.25(1H,d,J=7.2Hz),7.16−7.21(2H,m),7.59−7.6
4(4H,m),7.83−7.87(2H,m). IR(CHCl3):3446,3010,2946,2868,1745(sh),1728,16
50,1615,1525,1507,1486/cm. [α]D=+65.0゜(CHCl3,c=1.02,23℃) No.1m−16 CDCl3 300MHz 1.08−2.21(14H,m),2.34−2.40(5H,m),2.59(1H,
m),3.90(1H,m),5.29−5.48(2H,m),6.29(1H,d,J=
7.0Hz),7.18(2H,d,J=8.6Hz),7.58−7.64(4H,m),
7.83(2H,d,J=8.2Hz). IR(CHCl3):3438,3012,2948,2870,2622,1749,1710,164
9,1610,1526,1508,1487/cm. [α]D=+66゜(CHCl3,c=1.21,24℃) No.1m−17 CDCl3 300MHz 1.06−2.19(14H,m),2.32(2H,t,J=7.2Hz),2.62(1
H,m),3.63(3H,s),3.93(1H,m),5.30−5.50(2H,
m),6.32(1H,d,J=7.6Hz),6.41(1H,s),6.94(2H,d,
J=9.0Hz),7.47(2H,d,J=9.0Hz),7.58(2H,d,J=8.6
Hz),7.81(2H,d,J=8.6Hz). IR(CHCl3):3580,3434,3284,3010,2946,2868,1726,164
6,1606,1528,1490/cm. [α]D=+62.4゜(CHCl3,c=1.01,23℃) No.1m−18 CDCl3+CD3OD 300MHz 1.11−2.18(14H,m),2.32(2H,t,J=7.4Hz),2.59(1
H,m),3.88(1H,m),5.30−5.49(2H,m),6.55(1H,d,J
=7.0Hz),6.92(2H,d,J=8.6Hz),7.47(2H,d,J=8.6H
z),7.59(2H,d,J=8.6Hz),7.79(2H,d,J=8.2Hz). IR(Nujol):3398,3175,2725,1696,1635,1601,1531,150
1/cm. [α]D=+99.5゜(CH3OH,c=1.011,25℃) No.1m−19 CDCl3 300MHz 1.05−2.20(14H,m),2.32(2H,t,J=7.4Hz),2.61(1
H,m),3.63(3H,s),3.86(3H,s),3.94(1H,m),5.30
−5.50(2H,m),6.24(1H,d,J=7.0Hz),6.99(2H,d,J
=8.6Hz),7.53−7.63(4H,m),7.82(2H,d,J=8.6H
z). IR(CHCl3):3440,3006,2946,2875,1726,1649,1606,152
7,1510,1489/cm. [α]D=+68゜(CHCl3,c=0.88,26℃) No.1m−20 CDCl3 300MHz 1.09−2.20(14H,m),2.35(2H,t,J=7.3Hz),2.58(1
H,m),3.85(3H,s),3.89(1H,m),5.28−5.48(2H,
m),6.35(1H,d,J=7.2Hz),6.98(2H,d,J=8.8Hz),7.
51−7.61(4H,m),7.81(2H,d,J=8.4Hz),8.34(1H,b
s). IR(CHCl3):3446,3012,2952,2881,2640,1730(sh),17
07,1647,1606,1527,1510,1489/cm. [α]D=+83゜(CHCl3,c=1.00,25℃). No.1m−21 CDCl3 300MHz 1.05−2.14(14H,m),2.37(2H,t,J=7.2Hz),2.51(1
H,m),3.81(1H,m),5.34−5.46(2H,m),6.11(1H,d,J
=7.5Hz),7.33−7.48(3H,m),7.53−7.55(2H,m). IR(CHCl3):3420,3250,3008,2948,2870,2660,2210,173
5(sh),1705,1645,1503,1441,1409/cm. [α]D=+59.2±1.0゜(CHCl3,c=1.023,22℃). No.1m−22 CDCl3 300MHz 1.05−2.17(14H,m),2.37(2H,t,J=7.2Hz),2.52(1
H,m),3.82(1H,m),5.32−5.47(2H,m),6.20(1H,d,J
=7.6Hz),7.38−7.53(3H,m),7.58−7.61(6H,m),9.
11(1H,bs). IR(CHCl3):3420,3250,3010,2984,2870,2675,2208,173
0(sh),1705,1640,1500,1406/cm. [α]D=+57.4゜(CHCl3,c=1.83,23℃). No.1m−23 CDCl3 300MHz 1.05−2.18(14H,m),2.31(2H,t,J=7.5Hz),2.60(1
H,m),3.63(3H,s),3.90(1H,m),5.32−5.47(2H,
m),6.22(1H,d,J=6.9Hz),7.40−7.49(3H,m),7.76
−7.79(2H,m). IR(CHCl3):3438,3008,2946,2868,1727,1651,1603,158
5,1512,1484/cm. [α]D=+52゜(CHCl3,c=1.49,25℃). No.1m−24 CDCl3 300MHz 1.05−2.21(14H,m),2.36(2H,t,J=7.2Hz),2.57(1
H,m),3.89(1H,m),5.28−5.47(2H,m),6.22(1H,d,J
=7.0Hz),7.39−7.55(3H,m),7.73−7.79(2H,m). IR(CHCl3):3676,3572,3436,3010,2948,2875,1730(s
h),1709,1650,1600,1580,1514,1484/cm. [α]D=+57゜(CHCl3,c=0.97,26℃). No.1m−25 CDCl3 300MHz 1.04−2.18(14H,m),2.28−2.35(5H,m),2.59(1H,
m),3.62(3H,s),3.88(1H,m),5.29−5.49(2H,m),
6.20(1H,d,J=7.2Hz),7.15(2H,d,J=9.0Hz),7.80
(2H,d,J=8.8Hz). IR(CHCl3):3436,3010,2946,2868,1752,1727,1653,160
2,1519,1491/cm. [α]D=+53゜(CHCl3,c=1.63,25℃). No.1m−26 CDCl3 300MHz 1.05−2.19(14H,m),2.32−2.38(5H,m),2.56(1H,
m),3.88(1H,m),5.29−5.47(2H,m),6.25(1H,d,J=
7.4Hz),7.15(2H,d,J=9.0Hz),7.78(2H,d,J=8.6H
z). IR(CHCl3):3434,3016,3006,2948,2880,2622,1752,173
0(sh),1710,1651,1605,1520,1492/cm. [α]D=+58゜(CHCl3,c=3.68,24℃) No.1m−27 CDCl3 300MHz 1.05−2.16(14H,m),2.30(2H,t,J=7.5Hz),2.57(1
H,m),3.62(3H,s),3.87(1H,m),5.27−5.47(2H,
m),6.32(1H,d,J=7.4Hz),6.85(2H,d,J=8.6Hz),7.
62(2H,d,J=8.6Hz),8.35(1H,s). IR(CHCl3):3580,3450,3216,3010,2946,2868,1726,164
0,1608,1584,1528,1496/cm. [α]D=+56.2゜(CHCl3,c=0.713,23℃) No.1m−28 CDCl3 200MHz 1.10−2.25(14H,m),2.32(2H,t,J=7.2Hz),2.55(1
H,bs),3.82−3.93(1H,m),5.27−5.47(2H,m),6.25
(1H,d,J=7.4Hz),6.86(2H,d,J=8.6Hz),7.62(2H,
d,J=8.6Hz). IR(CHCl3):3438,3242,2675,1730(sh),1708,1639,16
07,1585/cm. No.1m−29 CDCl3 300MHz 1.05−2.18(14H,m),2.31(2H,t,J=7.4Hz),2.58(1
H,m),3.64(3H,s),3.85(3H,s),3.89(1H,m),5.29
−5.48(2H,m),6.14(1H,d,J=6.6Hz),6.92(2H,d,J
=9.0Hz),7.74(2H,d,J=9.0Hz). IR(CHCl3):3445,3008,2946,2868,1727,1646,1606,157
8,1523,1493/cm. [α]D=+53゜(CHCl3,c=2.03,24℃) No.1m−30 CDCl3 300MHz 1.04−2.21(14H,m),2.36(2H,t,J=7.3Hz),2.56(1
H,m),3.85(3H,s),3.88(1H,m),5.27−5.46(2H,
m),6.15(1H,d,J=7.2Hz),6.92(2H,d,J=8.6Hz),7.
73(2H,d,J=8.6Hz). IR(CHCl3):3440,3010,2950,2870,2645,1727,1710(s
h),1646,1606,1575,1524,1494/cm. [α]D=+62゜(CHCl3,c=1.01,24℃). No.1m−31 CDCl3+CD3OD 300MHz 1.16−2.20(14H,m),2.31(2H,t,J=7.2Hz),2.59(1
H,m),3.85(1H,m),5.31−5.51(2H,m),7.13−7.21
(1H,m),7.31−7.42(2H,m),7.68−7.93(6H,m). IR(Nujol):3344,3175,2715,2675,1699,1631,1566/cm. [α]D=+67゜(CH3OH,c=1.01,24℃). No.1m−32 CDCl3 200MHz 1.09−2.23(14H,m),2.33(2H,t,J=7.1Hz),2.57(1
H,bs),3.40−3.93(9H,m),4.41(1H,bs),5.29−5.48
(2H,m),6.44(1H,d,J=7.4Hz),7.43(2H,d,J=8.2H
z),7.80(2H,d,J=7.8Hz). IR(CHCl3)3434,3354,1726,1720(sh),1660(sh),16
26/cm. No.1m−33 CDCl3 200MHz 1.14−2.25(14H,m),2.37(2H,t,J=7.3Hz),2.64(1
H,bs),3.93−4.01(1H,m),5.30−5.51(2H,m),6.47
(1H,d,J=7.4Hz),7.63−7.74(2H,m),7.79(2H,s),
7.89−7.93(1H,m),8.00(1H,dd,J=2.3,1.0Hz),8.30
(1H,d,J=1.0Hz),8.65−8.73(2H,m). IR(CHCl3):3450,2675,1728,1707,1649,1528,1509/cm. [α]D=+82.8±1.2゜(CHCl3,c=1.01,23℃). No.2a−1 [α]D=+69.0゜(MeOH,c=1.01,25℃) No.2a−2 CDCl3 300MHz 0.99(1H,d,J=10.2Hz),1.15and1.24(each 3H,each
s),1.50−2.50(14H,m),4.30(1H,m),5.35−5.52(2
H,m),6.32(1H,d,J=8.7Hz),7.36−7.49(3H,m),7.5
8−7.62(2H,m),7.66and7.80(each 2H,each d,J=8.7
Hz). IR(CHCl3):3116,3014,2925,2870,2663,1708,1651,161
0,1524,1504,1484,1472/cm. [α]D=+64.1゜(MeOH,c=1.02,25℃). No.2a−3 [α]D=+76.6゜(MeOH,c=1.18,26℃). No.2a−4 CDCl3 300MHz 0.99(1H,d,J=10.2Hz),1.15and1.25(each 3H,each
s),1.64−2.51(14H,m),4.31(1H,m),5.36−5.53(2
H,m),6.33(1H,d,J=8.4Hz),7.50−7.56(3H,m),7.8
5−7.98(6H,m). IR(CHCl3):3515,3452,3014,2925,2870,1740,1708,165
4,1517,1486,1470/cm. [α]D=+79.5゜(MeOH,c=1.18,22℃). No.2a−5 CD3OD 300MHz 0.98(1H,d,J=9.9Hz),1.18and1.25(each 3H,each
s),1.56−1.71(3H,m),1.98−2.40(11H,m),4.17(1
H,m),5.41−5.52(2H,m),7.52−7.61(3H,m),7.91−
8.01(6H,m). IR(CHCl3):3416,3063,2983,2921,2869,1704,1643,156
6,1518,1488,1408/cm. [α]D=+62.0゜(MeOH,c=1.00,25℃). No.2a−6 [α]D=+64.1゜(MeOH,c=1.01,25℃). No.2a−7 [α]D=+65.3゜(MeOH,c=0.99,25℃). No.2a−8 [α]D=+74.0゜(MeOH,c=1.01,25℃). No.2a−9 [α]D=+71.0゜(MeOH,c=1.10,25℃). No.2a−10 [α]D=+74.7゜(MeOH,c=1.00,25℃). No.2a−11 [α]D=+72.1゜(MeOH,c=1.00,25℃). No.2a−12 [α]D=+53.1゜(CHCl3,c=1.01,26℃). m.p.155.0−156.0℃ No.2a−13 CDCl3 300MHz 0.98(1H,d,J=10.2Hz),1.18and1.25(each 3H,each
s),1.63−2.40(14H,m),4.30(1H,m),5.46−5.58(2
H,m),6.44(1H,d,J=8.4Hz),7.49and7.77(each 2H,e
ach d,J=8.7Hz),7.54(1H,s). IR(CHCl3):3689,3378,3028,3014,2924,1713,1652,160
2,1522,1496/cm. [α]D=+78.3゜(MeOH,c=0.84,25℃). m.p.205.0−206.0℃ No.2a−14 [α]D=+72.5゜(MeOH,c=1.07,25℃). No.2a−15 CDCl3 300MHz 0.99(1H,d,J=9.9Hz),1.14and1.24(each 3H,each
s),1.55−2.44(14H,m),4.27(1H,m),5.30−5.50(2
H,m),6.29(1H,d,J=9.0Hz),7.11and7.20(each 1H,e
ach d,J=16.2Hz),7.29−7.55(5H,m),7.57and7.72
(each 2H,each d,J=8.7Hz). IR(CHCl3):3453,3083,3022,3013,2925,2870,1708,165
0,1607,1560,1522,1496/cm. [α]D=+72.3゜(MeOH,c=1.00,27℃). m.p.115.0−117.0℃ No.2a−16 CDCl3 300MHz 0.92(1H,d,J=10.2Hz),1.11and1.23(each 3H,each
s),1.50−2.48(14H,m),3.62(3H,s),4.29(1H,m),
5.30−5.50(2H,m),6.20(1H,d,J=8.7Hz),6.59and6.
68(each 1H,each d,J=12.3Hz),7.23(5H,s),7.29an
d7.59(each 2H,each d,J=8.1Hz). IR(CHCl3):3453,3024,3016,2924,2870,1730,1651,160
7,1520,1495/cm. [α]D=+56.8゜(MeOH,c=1.04,24℃). No.2a−17 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.11and1.23(each 3H,each
s),1.50−2.38(14H,m),4.26(1H,m),5.30−5.50(2
H,m),6.23(1H,d,J=8.4Hz),6.59and6.70(each 1H,e
ach d,J=12.3Hz),7.23(5H,s),7.30and7.57(each 2
H,each d,J=8.7Hz). IR(CHCl3):3452,3081,3019,3014,2925,2870,2665,170
8,1650,1607,1521,1495/cm. [α]D=+61.6゜(MeOH,c=1.00,27℃). No.2a−18 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.11and1.23(each 3H,each
s),1.50−2.50(14H,m),3.61(3H,s),4.31(1H,m),
5.35−5.51(2H,m),6.33(1H,d,J=8.4Hz),7.48−7.6
4(4H,m),7.79−7.83(2H,m),7.91(1H,dt,J=1.5and
7.8Hz),8.01(1H,dt,J=1.5and7.8Hz),8.13(1H,t,J
=1.5Hz). IR(CHCl3):3450,3026,3013,2925,2870,1730,1659,160
0,1510/cm. [α]D=+56.0゜(MeOH,c=1.01,25℃). No.2a−19 CDCl3 300MHz 0.95(1H,d,J=9.9Hz),1.14and1.21(each 3H,each
s),1.53−2.60(14H,m),4.25(1H,m),5.35−5.64(2
H,m),7.21(1H,d,J=7.8Hz),7.49−7.68(4H,m),7.7
6−7.84(3H,m),8.25(1H,m),8.43(1H,m). IR(CHCl3):3382,3196,3025,3015,2925,2870,1725,165
2,1599,1577,1521/cm. [α]D=+55.9゜(MeOH,c=1.00,25℃). No.2a−20 CDCl3 300MHz 0.98(1H,d,J=10.2Hz),1.13and1.24(each 3H,each
s),1.50−2.50(14H,m),3.62(3H,s),4.31(1H,m),
5.35−5.51(2H,m),6.24(1H,d,J=8.4Hz),7.40−7.5
2(3H,m),7.71−7.76(2H,m). IR(CHCl3):3453,3025,3013,2925,2870,1730,1753,157
9,1514,1486/cm. [α]D=+61.2゜(MeOH,c=1.04,25℃). No.2a−21 CDCl3 300MHz 0.98(1H,d,J=10.2Hz),1.13and1.23(each 3H,each
s),1.52−2.50(14H,m),4.28(1H,m),5.34−5.51(2
H,m),6.27(1H,d,J=8.7Hz),7.41−7.53(3H,m),7.7
1−7.74(2H,m). IR(CHCl3):3452,3063,3027,3014,2925,2871,1708,165
2,1578,1515,1486/cm. [α]D=+62.0゜(MeOH,c=1.01,27℃). No.2a−22 d6−DMSO 300MHz 0.86(1H,d,J=9.9Hz),1.10and1.16(each 3H,each
s),1.42−1.52(3H,m),1.85−2.46(11H,m),3.98(1
H,m),5.32−5.43(2H,m),7.41(3H,m),7.88(2H,d,J
=6.6Hz),8.19(1H,d,J=6.6Hz). IR(KBr):3367,3060,2984,2922,2868,1634,1563,1529,
1487/cm. [α]D=+47.7゜(MeOH,c=1.00,25℃). No.2a−23 [α]D=+62.7゜(MeOH,c=1.01,27℃). No.2a−24 CDCl3 300MHz 0.99(1H,d,J=10.2Hz),1.14and1.25(each 3H,each
s),1.52−2.50(14H,m),4.31(1H,m),5.36−5.52(2
H,m),6.34(1H,d,J=8.4Hz),7.47−7.52(2H,m),7.5
9−7.64(1H,m),7.78−7.83(6H,m). IR(CHCl3):3449,3027,3013,2925,2869,1708,1656,159
9,1518,1493/cm. [α]D=+63.1゜(MeOH,c=1.00,25℃). No.2a−25 [α]D=+35.1゜(MeOH,c=1.00,25℃). No.2a−26 [α]D=+35.5゜(MeOH,c=1.02,25℃). No.2a−27 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.12and1.23(each 3H,each
s),1.52−2.50(14H,m),3.63(3H,s),4.29(1H,m),
5.36−5.51(2H,m),6.18(1H,d,J=8.4Hz),7.01and7.
71(each 2H,each d,J=8.7Hz),6.98−7.05(2H,m),
7.16(1H,t,J=7.5Hz),7.34−7.41(2H,m). IR(CHCl3):3455,3024,3016,2924,2870,1730,1651,158
8,1520,1487/cm. [α]D=+56.4゜(MeOH,c=1.01,25℃). No.2a−28 CDCl3 300MHz 0.98(1H,d,J=10.2Hz),1.12and1.23(each 3H,each
s),1.52−2.50(14H,m),4.26(1H,m),5.34−5.51(2
H,m),6.20(1H,d,J=9.0Hz),7.01and7.70(each 2H,e
ach d,J=9.0Hz),6.98−7.15(2H,m),7.17(1H,t,J=
7.5Hz),7.34−7.40(2H,m). IR(CHCl3):3454,3031,3018,2925,2870,1708,1650,158
8,1523,1487/cm. [α]D=+56.2゜(MeOH,c=1.00,25℃). No.2a−29 [α]D=+53.0゜(MeOH,c=1.03,25℃). No.2a−30 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.10and1.23(each 3H,each
s),1.52−2.50(14H,m),4.25(1H,m),5.30−5.50(2
H,m),6.23(1H,d,J=8.7Hz),6.36(1H,s),7.26−7.3
9(10H,m),7.60and7.68(each 2H,each d,J=8.4H
z). IR(CHCl3):3451,3088,3064,3029,3014,2925,2869,170
7,1652,1522,1495/cm. [α]D=+54.2゜(MeOH,c=1.00,25℃). No.2a−31 CDCl3 300MHz 0.98(1H,d,J=10.2Hz),1.14and1.24(each 3H,each
s),1.50−2.50(14H,m),3.63(3H,s),4.31(1H,m),
5.30−5.50(2H,m),6.26(1H,d,J=8.4Hz),6.90(1H,
d,J=7.4Hz),7.13(1H,d,J=8.7Hz),7.29(2H,t,J=
8.0Hz),7.67−7.75(5H,m),7.82(1H,s). IR(Nuj4ol):3380,3244,1723,1638,1601,1578,1535,14
95/cm. [α]D=+73.6゜(MeOH,c=0.50,26℃). m.p.133.0−134.0℃ No.2a−32 [α]D=+56.1゜(MeOH,c=1.02,26℃). No.2a−33 CDCl3 300MHz 0.95(1H,d,J=10.2Hz),1.10and1.21(each 3H,each
s),1.50−2.50(14H,m),4.25(1H,m),5.13(2H,s),
5.30−5.70(3H,m),6.41(1H,d,J=8.2Hz),6.89(1H,
s),7.09(1H,s),7.17and7.72(each 2H,each d,J=8.
2Hz),7.62(1H,s). IR(CHCl3):3450,3125,3031,3013,2925,2870,2467,191
7,1708,1654,1615,1575,1523,1497/cm. [α]D=+55.2゜(MeOH,c=1.01,26℃). No.2a−34 [α]D=+72.9゜(MeOH,c=1.03,25℃). No.2a−35 CDCl3 300MHz 0.98(1H,d,J=10.2Hz),1.13and1.24(each 3H,each
s),1.52−2.48(14H,m),4.28(1H,m),5.35−5.51(2
H,m),6.28(1H,d,J=8.7Hz),7.34−7.37(3H,m),7.5
2−7.55(2H,m),7.58and7.71(each 2H,each d,J=8.7
Hz). IR(CHCl3):3515,3452,3030,3012,2925,2870,1739,170
8,1652,1607,1555,1521,1497/cm. [α]D=+74.3゜(MeOH,c=1.01,25℃). No.2a−36 [α]D=+23.4゜(MeOH,c=1.07,25℃). No.2a−37 CDCl3 300MHz 0.83(1H,d,J=10.5Hz),0.95and1.18(each 3H,each
s),1.44−2.46(14H,m),3.92(1H,m),5.34−5.52(3
H,m),7.26−7.54(9H,m),7.62(1H,s). IR(CHCl3):3432,3310,3189,3023,3014,2924,2870,170
4,1610,1594,1523,1487/cm. [α]D=+25.3゜(MeOH,c=1.00,26℃). No.2a−38 [α]D=+70.9゜(MeOH,c=1.02,25℃). No.2a−39 [α]D=+70.6゜(MeOH,c=1.01,25℃). No.2a−40 [α]D=+74.7゜(MeOH,c=1.00,25℃). No.2a−41 [α]D=+72.1゜(MeOH,c=1.01,24℃). No.2a−42 [α]D=+69.2゜(MeOH,c=1.00,25℃). No.2a−43 [α]D=+70.8゜(MeOH,c=1.00,25℃). No.2a−44 [α]D=+60.4゜(MeOH,c=1.00,26℃). No.2a−45 CDCl3 300MHz 0.97(1H,d,J=9.9Hz),1.13and1.23(each 3H,each
s),1.55−2.52(14H,m),4.29(1H,m),5.34−5.54(2
H,m),6.33(1H,d,J=9.0Hz),7.10(1H,t,J=7.4Hz),
7.34(2H,t,J=7.4Hz),7.52(2H,m),7.68and7.75(ea
ch 2H,each d,J=8.4Hz),7.80(1H,s),8.10(1H,s),
10.09(1H,s). IR(CHCl3):3393,3195,3093,3033,3013,2925,2870,169
8,1656,1598,1537,1498/cm. [α]D=+59.4゜(MeOH,c=1.01,24℃). No.2a−46 [α]D=+63.5゜(MeOH,c=1.00,25℃). No.2a−47 CDCl3 300MHz 0.97(1H,d,J=9.9Hz),1.12and1.23(each 3H,each
s),1.54−2.48(14H,m),4.29(1H,m),5.35−5.52(2
H,m),6.32(1H,d,J=8.7Hz),7.26(1H,m),7.41(2H,
t,J=7.8Hz),7.64(2H,d,J=7.5Hz),7.73and7.77(ea
ch 2H,each d,J=8.4Hz),7.95(1H,s),9.20(1H,s),
10.38(1H,s). IR(CHCl3):3450,3339,3003,2992,2925,2870,1706,165
3,1596,1523,1495/cm. [α]D=+63.3゜(MeOH,c=1.00,25℃). No.2a−48 [α]D=+63.8゜(MeOH,c=1.00,24℃). No.2a−49 CDCl3 300MHz 1.00(1H,d,J=10.5Hz),1.17and1.26(each 3H,each
s),1.55−2.52(14H,m),4.34(1H,m),5.36−5.54(2
H,m),6.35(1H,d,J=9.0Hz),7.50−7.62(3H,m),7.9
0and8.33(each 2H,each d,J=8.4Hz),8.21(2H,m). IR(CHCl3):3451,3029,3022,3016,2925,2870,1708,165
5,1542,1508,1498,1471,1459/cm. [α]D=+63.5゜(MeOH,c=1.02,25℃). m.p.135.0−137.0℃ No.2a−50 [α]D=+68.9゜(MeOH,c=1.01,24℃). No.2a−51 d6−DMSO 300MHz 0.87(1H,d,J=9.9Hz),1.10and1.17(each 3H,each
s),1.40−1.60(3H,m),1.90−2.40(11H,m),3.98(1
H,m),5.35−5.46(2H,m),7.64(1H,s),7.65and7.91
(each 2H,each d,J=8.7Hz),8.06(1H,d,J=6.0Hz),
9.32(1H,bs). IR(KBr):3385,2962,1734,1707,1632,1529,1498/cm. [α]D=+68.4゜(MeOH,c=1.01,24℃). No.2a−52 [α]D=+76.2゜(MeOH,c=1.01,24℃). No.2a−53 [α]D=+73.9゜(MeOH,c=1.02,24℃). No.2a−54 [α]D=+68.1゜(MeOH,c=1.00,24℃). No.2a−55 [α]D=+67.8゜(MeOH,c=1.00,24℃). No.2a−56 [α]D=+65.4゜(MeOH,c=1.03,25℃). No.2a−57 [α]D=+63.4゜(MeOH,c=1.01,24℃). No.2a−58 [α]D=+66.6゜(MeOH,c=1.01,24℃). No.2a−59 [α]D=+65.5゜(MeOH,c=1.00,24℃). No.2a−60 [α]D=+60.9゜(MeOH,c=1.02,25℃). No.2a−61 CDCl3 300MHz 0.97(1H,d,J=10.0Hz),1.10and1.22(each 3H,each
s),1.50−2.50(14H,m),4.26(1H,m),5.30−5.54(2
H,m),6.28(1H,d,J=8.6Hz),6.60and6.82(each 1H,e
ach d,J=12.4Hz),7.12(2H,d,J=6.0Hz),7.25and7.6
2(each 2H,each d,J=8.6Hz),8.47(2H,d,J=6.0H
z). IR(CHCl3):3452,3027,3019,3013,2925,2870,2480,170
8,1651,1606,1520,1494/cm. [α]D=+61.6゜(MeOH,c=1.01,25℃). No.2a−62 [α]D=+72.0゜(MeOH,c=0.93,25℃). No.2a−63 CDCl3 300MHz 0.99(1H,d,J=10.2Hz),1.14and1.24(each 3H,each
s),1.50−2.50(14H,m),4.29(1H,m),5.36−5.55(2
H,m),6.35(1H,d,J=9.1Hz),7.04and7.27(each 1H,e
ach d,J=16.5Hz),7.37(2H,d,J=6.6Hz),7.56and7.7
6(each 2H,each d,J=8.4Hz),8.57(2H,d,J=6.6H
z). IR(CHCl3):3452,3024,3018,3014,2925,2870,2470,193
3,1708,1652,1605,1521,1496/cm. [α]D=+69.2゜(MeOH,c=1.01,25℃). No.2a−64 [α]D=+56.9゜(MeOH,c=1.24,25℃). No.2a−65 CDCl3 300MHz 0.98(1H,d,J=10.5Hz),1.12and1.23(each 3H,each
s),1.54−2.46(14H,m),4.27(1H,m),5.23(2H,s),
5.34−5.52(2H,m),6.26(1H,d,J=8.4Hz),7.32−7.4
5(5H,m),7.64and7.71(each 2H,each d,J=8.4Hz),
8.15(1H,s). IR(CHCl3):3452,3088,3065,3032,3013,2925,2870,170
8,1653,1611,1559,1522,1496/cm. [α]D=+61.0゜(MeOH,c=0.91,25℃). No.2a−66 [α]D=+76.0゜(MeOH,c=1.01,25℃). No.2a−67 CDCl3 300MHz 0.98(1H,d,J=10.4Hz),1.14and1.24(each 3H,each
s),1.54−2.46(14H,m),4.28(1H,m),5.32−5.53(2
H,m),6.27(1H,d,J=8.6Hz),6.92−7.31(each 1H,ea
ch d,J=16.4Hz),7.02(1H,dd,J=5.8and3.6Hz),7.12
(1H,d,J=3.6Hz),7.24(1H,d,J=5.8Hz),7.51and7.7
0(each 2H,each d,J=8.4Hz). IR(CHCl3):3453,3029,3013,2925,2870,1739,1650,160
4,1524,1515,1494/cm. [α]D=+76.2゜(MeOH,c=1.00,24℃). m.p.104.0−106.0℃ No.2a−68 [α]D=+57.7゜(MeOH,c=1.01,25℃). No.2a−69 CDCl3 300MHz 0.99(1H,d,J=10.2Hz),1.14and1.24(each 3H,each
s),1.54−2.48(14H,m),4.28(1H,m),5.34−5.53(2
H,m),6.29(1H,d,J=9.0Hz),6.54−6.74(each 1H,ea
ch d,J=12.0Hz),7.02(1H,dd,J=4.8and3.3Hz),6.97
(1H,dd,J=3.3and1.2Hz),7.13(1H,dd,J=4.8and1.2H
z),7.44and7.70(each 2H,each d,J=8.7Hz). IR(CHCl3):3453,3025,3010,2925,2870,1708,1650,160
7,1559,1523,1493/cm. [α]D=+58.4゜(MeOH,c=1.00,25℃). No.2a−70 [α]D=+48.6゜(MeOH,c=1.00,25℃). No.2a−71 CDCl3 300MHz 0.98(1H,d,J=10.2Hz),1.12and1.23(each 3H,each
s),1.52−2.46(14H,m),2.31(3H,s),4.26(1H,m),
5.33−5.52(2H,m),6.20(1H,d,J=9.3Hz),7.02−7.1
1(6H,m),7.70(2H,d,J=9.0Hz). IR(CHCl3):3460,3031,3022,3011,2925,2870,1750,170
8,1650,1608,1597,1523,1490/cm. [α]D=+48.9゜(MeOH,c=1.01,25℃). No.2a−72 [α]D=+51.2゜(MeOH,c=1.02,25℃). No.2a−73 CDCl3 300MHz 0.97(1H,d,J=9.9Hz),1.11and1.23(each 3H,each
s),1.54−2.48(14H,m),4.27(1H,m),5.32−5.52(2
H,m),6.24(1H,d,J=9.0Hz),6.83−6.94(6H,m),7.6
5(2H,d,J=9.0Hz). IR(CHCl3):3598,3451,3199,3033,3012,2925,2870,170
8,1642,1604,1524,1507,1491/cm. [α]D=+52.2゜(MeOH,c=1.01,25℃). No.2a−74 [α]D=+51.5゜(MeOH,c=0.92,25℃). No.2a−75 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.11and1.23(each 3H,each
s),1.55−2.46(14H,m),3.82(3H,s),4.25(1H,m),
5.32−5.52(2H,m),6.19(1H,d,J=8.7Hz),6.89−7.0
1(6H,m),7.65−7.68(2H,m). IR(CHCl3):3450,3025,3008,2925,2870,2837,1741,164
9,1612,1521,1505,1490/cm. [α]D=+51.1゜(MeOH,c=1.00,25℃). No.2a−76 [α]D=+60.4゜(MeOH,c=0.98,25℃). No.2a−77 CDCl3 300MHz 0.99(1H,d,J=10.5Hz),1.15and1.24(each 3H,each
s),1.54−2.48(14H,m),2.34(3H,s),4.29(1H,m),
5.32−5.54(2H,m),6.32(1H,d,J=8.4Hz),7.19and7.
60(each 2H,each d,J=8.4Hz),7.63and7.79(each 2
H,each d,J=8.4Hz). IR(CHCl3):3452,3027,3012,2925,2870,1751,1709,165
1,1611,1560,1527,1509,1489/cm. [α]D=+61.2゜(MeOH,c=1.00,25℃). No.2a−78 [α]D=+67.4゜(MeOH,c=1.01,25℃). No.2a−79 CDCl3 300MHz 0.99(1H,d,J=10.2Hz),1.15and1.24(each 3H,each
s),1.54−2.54(14H,m),4.31(1H,m),5.32−5.54(2
H,m),6.36(1H,d,J=8.2Hz),6.93and7.48(each 2H,e
ach d,J=8.6Hz),7.59and7.75(each 2H,each d,J=8.
4Hz). IR(CHCl3):3593,3448,3192,3030,3010,2925,2870,170
8,1644,1608,1591,1559,1530,1516,1491/cm. [α]D=+65.8゜(MeOH,c=1.01,25℃). No.2a−80 [α]D=+66.9゜(MeOH,c=1.01,25℃). No.2a−81 CDCl3 300MHz 0.99(1H,d,J=10.5Hz),1.15and1.24(each 3H,each
s),1.54−2.48(14H,m)3.86(3H,s),4.29(1H,m),
5.34−5.52(2H,m),6.20(1H,d,J=8.7Hz),6.99and7.
55(each 2H,each d,J=9.0Hz),7.61and7.77(each 2
H,each d,J=8.7Hz). IR(CHCl3):3450,3009,2925,2870,2838,1740,1708,165
0,1608,1557,1528,1512,1491/cm. [α]D=+66.2゜(MeOH,c=1.01,25℃). No.2a−82 [α]D=+57.7゜(MeOH,c=1.02,24℃). No.2a−83 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.12and1.23(each 3H,each
s),1.54−2.48(14H,m),2.33(3H,s),4.26(1H,m),
5.32−5.52(2H,m),6.25(1H,d,J=8.7Hz),7.16and7.
75(each 2H,each d,J=8.7Hz). IR(CHCl3):3452,3030,3022,3012,2925,2870,1754,170
9,1654,1604,1585,1522,1493/cm. [α]D=+57.4゜(MeOH,c=1.01,24℃). No.2a−84 [α]D=+57.8゜(MeOH,c=1.01,24℃). No.2a−85 CDCl3 300MHz 0.95(1H,d,J=10.2Hz),1.12and1.22(each 3H,each
s),1.54−2.48(14H,m),4.25(1H,m),5.32−5.52(2
H,m),6.28(1H,d,J=8.7Hz),6.87and7.57(each 2H,e
ach d,J=9.0Hz). IR(CHCl3):3590,3450,3166,3019,3012,2925,2871,170
8,1637,1608,1583,1531,1498/cm. [α]D=+56.0゜(MeOH,c=1.01,24℃). No.2a−86 [α]D=+59.3゜(MeOH,c=1.01,22℃). No.2a−87 CDCl3 300MHz 0.98(1H,d,J=10.0Hz),1.13and1.23(each 3H,each
s),1.54−2.48(14H,m),3.85(3H,s),4.25(1H,m),
5.32−5.53(2H,m),6.19(1H,d,J=8.8Hz),6.93and7.
69(each 2H,each d,J=9.0Hz). IR(CHCl3):3450,3030,3017,3012,2925,2870,2840,174
0,1708,1647,1606,1575,1525,1496/cm. [α]D=+58.2゜(MeOH,c=0.99,22℃). No.2a−88 [α]D=+50.9゜(MeOH,c=1.02,25℃). No.2a−89 CDCl3 300MHz 0.99(1H,d,J=10.2Hz),1.18and1.26(each 3H,each
s),1.56−2.48(14H,m),4.29(1H,m),5.36−5.54(2
H,m),7.03(1H,d,J=8.7Hz),7.21(1H,s),7.43(2H,
m),7.74(1H,ddd,J=1.8,6.9and8.7Hz),8.22(1H,dd,
J=1.8and8.1Hz). IR(CHCl3):3443,3087,3023,3014,2925,2870,1708,168
5,1658,1630,1517,1466/cm. [α]D=+57.1゜(MeOH,c=1.01,25℃). m.p.117.0−118.0℃ No.2a−90 [α]D=+54.1゜(MeOH,c=1.01,22℃). No.2a−91 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.13and1.23(each 3H,each
s),1.52−2.46(14H,m),4.24(1H,m),5.34−5.52(2
H,m),6.49−6.53(2H,m),7.11(1H,dd,J=0.9and3.6H
z),7.44(1H,dd,J=0.9and1.8Hz). IR(CHCl3):3437,3033,3022,3014,2925,2870,1739,170
8,1655,1595,1520,1472/cm. [α]D=+55.0゜(MeOH,c=1.00,22℃). No.2a−92 [α]D=+50.3゜(MeOH,c=1.00,22℃). No.2a−93 CDCl3 300MHz 0.95(1H,d,J=10.5Hz),1.12and1.23(each 3H,each
s),1.52−2.46(14H,m),4.25(1H,m),5.34−5.52(2
H,m),6.12(1H,d,J=8.7Hz),7.07(1H,dd,J=3.9and
5.1Hz),7.45−7.48(2H,m). IR(CHCl3):3450,3023,3011,2925,2870,1739,1708,164
5,1531,1501,1471/cm. [α]D=+49.1゜(MeOH,c=1.02,24℃). No.2a−94 [α]D=+51.5゜(MeOH,c=1.00,24℃). No.2a−95 CDCl3 300MHz 0.96(1H,d,J=10.5Hz),1.11and1.23(each 3H,each
s),1.52−2.46(14H,m),4.25(1H,m),5.34−5.56(2
H,m),6.14(1H,d,J=8.7Hz),7.34(2H,d,J=2.0Hz),
7.85(1H,t,J=2.0Hz). IR(CHCl3):3452,3114,3030,3013,2925,2870,1708,164
9,1535,1498,1471/cm. [α]D=+55.5゜(MeOH,c=1.00,25℃). m.p.87.0−88.0℃ No.2a−96 CD3OD 300MHz 0.94(1H,d,J=10.2Hz),1.13and1.22(each 3H,each
s),1.50−1.76(3H,m),1.94−2.39(11H,m),4.11(1
H,m),5.39−5.49(2H,m),7.43−7.51(2H,m),8.05
(1H,m). IR(KBr):3369,3084,2985,2921,2868,1630,1566,1538,
1503/cm. [α]D=+38.8゜(MeOH,c=1.01,22℃). No.2a−97 CD3OD 300MHz 0.93(1H,d,J=9.9Hz),1.13and1.22(each 3H,each
s),1.48−1.58(3H,m),1.96−2.36(11H,m),4.10(1
H,m),5.35−5.50(2H,m),7.42−7.51(2H,m),8.06
(1H,m). IR(KBr):3447,3087,2987,2922,2868,1629,1545,1501/
cm. [α]D=+52.9゜(MeOH,c=1.01,24℃). No.2a−98 [α]D=+53.2゜(MeOH,c=1.02,23℃). No.2a−99 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.12and1.22(each 3H,each
s),1.26−2.45(24H,m),4.25(2H,m),5.34−5.52(2
H,m),6.18(1H,d,J=8.7Hz),6.91and7.66(each 2H,e
ach d,J=9.0Hz). IR(CHCl3):3455,3029,3019,2939,2862,1738,1709,164
5,1605,1523,1494/cm. [α]D=+51.4゜(MeOH,c=1.00,23℃). No.2a−100 [α]D=+49.3゜(MeOH,c=1.00,24℃). No.2a−101 [α]D=+51.3゜(MeOH,c=1.00,24℃). No.2a−102 [α]D=+48.8゜(MeOH,c=1.01,23℃). No.2a−103 CDCl3 300MHz 0.94(1H,d,J=10.2Hz),1.12and1.22(each 3H,each
s),1.52−2.46(14H,m),2.48(3H,d,J=0.3Hz),4.20
(1H,m),5.32−5.54(2H,m),6.46(1H,bs),7.12(1
H,d,J=9.0Hz). IR(CHCl3):3415,3144,3029,3011,2926,2871,1708,167
1,1598,1538,14564/cm. [α]D=+49.6゜(MeOH,c=1.01,23℃). No.2a−104 [α]D=+77.0゜(MeOH,c=1.02,23℃). No.2a−105 CDCl3 300MHz 0.93(1H,d,J=9.9Hz),1.09and1.21(each 3H,each
s),1.51−2.44(14H,m),3.90(6H,s),4.20(1H,m),
5.38−5.50(2H,m),5.87(1H,d,J=9.0Hz),6.25and7.
54(each 1H,each d,J=15.6Hz),6.84(1H,d,J=8.1H
z),7.03(1H,d,J=1.8Hz),7.09(1H,dd,J=1.8and8.1
Hz). IR(CHCl3):3439,3028,3012,2937,2871,2841,1739,170
8,1661,1620,1600,1513/cm. [α]D=+77.3゜(MeOH,c=1.01,23℃). No.2a−106 [α]D=+67.0゜(MeOH,c=1.00,25℃). No.2a−107 [α]D=+66.6゜(MeOH,c=1.01,24℃). m.p.168.0−170.0℃ No.2a−108 [α]D=+61.8゜(MeOH,c=1.00,22℃). No.2a−109 CDCl3 300MHz 0.96(1H,d,J=10.2Hz),1.10and1.22(each 3H,each
s),1.51−2.45(14H,m),4.25(1H,m),5.35−5.49(2
H,m),6.21(1H,d,J=8.7Hz),7.25and7.60(each 2H,e
ach d,J=8.7Hz),7.33−7.41(5H,s). IR(CHCl3):3453,3062,3028,3014,2925,2870,1739,170
8,1651,1594,1557,1515,1481/cm. [α]D=+61.0゜(MeOH,c=1.01,22℃). No.2a−110 CD3OD 300MHz 0.94(1H,d,J=9.9Hz),1.13and1.22(each 3H,each
s),1.54−2.37(14H,m),4.12(1H,m),5.38−5.49(2
H,m),7.25and7.68(each 2H,each d,J=8.7Hz),7.41
(5H,s). IR(KBr):3435,3058,2986,2920,2866,1635,1595,1562,
1521,1482,1439,1411/cm. [α]D=+47.3゜(MeOH,c=1.01,23℃). No.2a−111 [α]D=+65.6゜(MeOH,c=1.01,24℃). No.2a−112 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.12and1.23(each 3H,each
s),1.51−2.46(14H,m),4.27(1H,m),5.35−5.50(2
H,m),6.22(1H,d,J=8.4Hz),7.40and7.66(each 2H,e
ach d,J=9.0Hz). IR(CHCl3):3439,3028,3012,2937,2871,2841,1739,170
8,1661,1620,1600,1513/cm. [α]D=+65.6゜(MeOH,c=1.01,22℃). No.2a−113 [α]D=+59.6゜(MeOH,c=1.00,24℃). No.2a−114 CDCl3 300MHz 0.98(1H,d,J=10.2Hz),1.12and1.24(each 3H,each
s),1.52−2.46(14H,m),4.29(1H,m),5.33−5.51(2
H,m),6.28(1H,d,J=8.4Hz),7.70and7.83(each 2H,e
ach d,J=8.4Hz). IR(CHCl3):3439,3028,3012,2937,2871,2841,1739,170
8,1661,1620,1600,1513/cm. [α]D=+60.6゜(MeOH,c=1.01,22℃). No.2a−115 [α]D=+59.7゜(MeOH,c=0.99,24℃). No.2a−116 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.12and1.23(each 3H,each
s),1.52−2.46(14H,m),2.39(3H,s),4.27(1H,m),
5.33−5.51(2H,m),6.24(1H,d,J=9.0Hz),7.23and7.
62(each 2H,each d,J=8.4Hz). IR(CHCl3):3439,3028,3012,2937,2871,2841,1739,170
8,1661,1620,1600,1513/cm. [α]D=+59.7゜(MeOH,c=0.99,24℃). No.2a−117 [α]D=+56.7゜(MeOH,c=1.00,23℃). No.2a−118 CDCl3 300MHz 0.96(1H,d,J=10.2Hz),1.11and1.23(each 3H,each
s),1.53−2.44(14H,m),4.23(1H,m),5.34−5.51(2
H,m),6.02(2H,s),6.13(1H,d,J=8.7Hz),6.83(1H,
dd,J=1.2and7.8Hz),7.22−7.25(2H,m). IR(CHCl3):3453,3031,3020,3012,2924,2870,1740,170
8,1650,1619,1605,1519,1504,1480/cm. [α]D=+57.2゜(MeOH,c=1.02,23℃). No.2a−119 CDCl3 300MHz 0.96(1H,d,J=10.5Hz),1.07and1.23(each 3H,each
s),1.51−2.44(14H,m),2.32(3H,s),4.26(1H,m),
5.37−5.52(2H,m),6.40(1H,d,J=9.0Hz),7.09(1H,
m),7.30(1H,m),7.46(1H,m),7.66(1H,m). IR(CHCl3):3443,3028,3012,2925,2870,1766,1747,170
9,1657,1607,1516,1479/cm. [α]D=+53.2゜(MeOH,c=0.99,21℃). No.2a−120 CDCl3 300MHz 0.98(1H,d,J=10.2Hz),1.14and1.24(each 3H,each
s),1.53−2.44(14H,m),4.30(1H,m),5.35−5.52(2
H,m),6.42(1H,d,J=8.7Hz),6.85(1H,m),6.99(1H,
dd,J=1.2and8.4Hz),7.27(1H,m),7.39(1H,m). IR(CHCl3):3463,3033,3021,3014,2992,2924,2870,170
8,1643,1597,1523,1488/cm. [α]D=+46.3゜(MeOH,c=1.01,21℃). No.2a−121 CDCl3 300MHz 0.98(1H,d,J=10.2Hz),1.14and1.23(each 3H,each
s),1.47−2.47(14H,m),3.95(3H,s),4.31(1H,m),
5.32−5.50(2H,m),6.98(1H,dd,J=0.9and8.4Hz),7.
09(1H,ddd,J=0.9,7.7and8.4Hz),7.45(1H,m),8.19
(1H,dd,J=2.1and8.1Hz),8.32(1H,d,J=9.Hz). IR(CHCl3):3400,3078,3028,3020,3007,2924,2870,284
2,1736,1708,1640,1600,1536,1483,1470/cm. [α]D=+38.1゜(MeOH,c=1.02,23℃). No.2a−122 [α]D=+42.3゜(MeOH,c=0.99,23℃). No.2a−123 [α]D=+38.7゜(MeOH,c=1.00,21℃). No.2a−124 [α]D=+45.0゜(MeOH,c=1.01,21℃). m.p.119.0−120.0℃ No.2a−125 [α]D=+49.8゜(MeOH,c=1.01,22℃). No.2a−126 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.11and1.23(each 3H,each
s),1.52−2.47(14H,m),4.26(1H,m),5.34−5.50(2
H,m),6.22(1H,d,J=8.7Hz),7.55−7.61(4H,m). IR(CHCl3):3400,3078,3028,3020,3007,2924,2870,284
2,1736,1708,1640,1600,1536,1483,1470/cm. [α]D=+63.0゜(MeOH,c=1.01,23℃). No.2a−127 CDCl3 300MHz 0.91(1H,d,J=10.2Hz),1.10and1.20(each 3H,each
s),1.50−2.42(14H,m),4.23(1H,m),5.31−5.51(2
H,m),6.45(1H,d,J=8.4Hz),7.01(1H,d,J=7.4Hz),
7.22−7.27(2H,m),7.33−7.40(4H,m),7.53(2H,d,J
=9.0Hz),8.30and8.49(each 1H,each s). IR(CHCl3):3452,3028,3022,3015,2925,2870,1708,165
4,1590,1514,1478/cm. [α]D=+59.5゜(MeOH,c=1.01,23℃). No.2a−128 d6−DMSO 300MHz 0.84(1H,d,J=9.9Hz),1.06and1.19(each 3H,each
s),1.37−2.37(14H,m),3.79(1H,m),5.35−5.51(2
H,m),6.08(1H,d,J=8.7Hz),6.85−6.90(1H,m),7.1
8−7.23(2H,m),7.35−7.38(2H,m),8.42(1H,s),1
2.00(1H,s). IR(Nujol):3395,3345,2925,2866,2623,2506,1697,165
8,1638,1597,1557/cm. [α]D=+26.0゜(MeOH,c=1.01,23℃). m.p.164.0−166.0℃ No.2a−129 CDCl3 300MHz 1.01(1H,d,J=10.0Hz),1.17and1.25(each 3H,each
s),1.54−2.52(14H,m),4.34(1H,m),5.36−5.57(2
H,m),6.42(1H,d,J=8.6Hz),7.51−7.60(2H,m),7.7
7(1H,dd,J=1.8and8.6Hz),7.85−7.96(3H,m),8.24
(1H,bs). IR(CHCl3):3451,3060,3028,3010,2925,2870,1708,165
2,1629,1600,1517,1502/cm. [α]D=+68.6゜(MeOH,c=1.00,22℃) No.2a−130 CDCl3 300MHz 1.02(1H,d,J=10.2Hz),1.04and1.26(each 3H,each
s),1.54−2.52(14H,m),4.41(1H,m),5.41−5.58(2
H,m),6.14(1H,d,J=9.0Hz),7.43−7.59(4H,m),7.8
5−7.92(2H,m),8.27(1H,dd,J=1.8and7.2Hz). IR(CHCl3):3436,3032,3010,2924,2870,2664,1708,165
2,1512,1498/cm. [α]D=+93.9゜(MeOH,c=1.00,22℃). m.p.94.0−96.0℃ No.2a−131 [α]D=+50.2゜(MeOH,c=0.95,21℃). No.2a−132 [α]D=+10.9゜(MeOH,c=0.92,21℃). No.2a−133 [α]D=+60.4゜(MeOH,c=1.00,21℃). No.2a−134 [α]D=+38.5゜(MeOH,c=1.01,23℃). No.2a−135 [α]D=+52.5゜(MeOH,c=1.01,23℃). m.p.180.0−182.0℃ No.2a−136 [α]D=+35.3゜(MeOH,c=1.02,23℃). m.p.79.0−80.0℃ No.2a−137 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.11and1.22(each 3H,each
s),1.43(3H,t,J=6.9Hz),1.52−2.44(14H,m),4.03
(2H,q,J=9.6Hz),4.26(1H,m),5.33−5.50(2H,m),
6.19(1H,d,J=8.7Hz),6.88−7.00(6H,m),7.65−7.6
8(2H,m). IR(CHCl3):3455,3031,3024,3014,2988,2925,2870,174
1,1708,1649,1602,1521,1504,1490/cm. [α]D=+52.0゜(MeOH,c=1.01,23℃). No.2a−138 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.11and1.22(each 3H,each
s),1.35(6H,d,J=6.0Hz),1.53−2.46(14H,m),4.25
(1H,m),4.51(1H,m),5.33−5.50(2H,m),6.12(1H,
d,J=9.0Hz),6.87−6.99(6H,m),7.65−7.68(2H,
m). IR(CHCl3):3454,3031,3014,2980,2925,2870,1741,170
8,1649,1602,1522,1490/cm. [α]D=+50.0゜(MeOH,c=1.05,22℃). No.2a−139 CDCl3 300MHz 1.00(1H,d,J=10.2Hz),1.16and1.24(each 3H,each
s),1.59−2.52(14H,m),4.31(1H,m),5.40−5.53(2
H,m),6.36(1H,d,J=8.7Hz),6.70(1H,d,J=1.5Hz),
7.12(1H,m),7.30(1H,m),7.47(1H,dd,J=0.6and8.1
Hz),7.61(1H,d,J=8.4Hz). IR(CHCl3):3449,3243,3029,3022,3013,2925,2871,170
7,1631,1542,1505/cm. [α]D=+63.4゜(MeOH,c=1.00,23℃). m.p.178.0−179.0℃ No.2a−140 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.18and1.23(each 3H,each
s),1.57−2.50(14H,m),4.35(1H,m),5.32−5.55(2
H,m),6.42(1H,d,J=8.7Hz),6.70(1H,d,J=1.5Hz),
7.21−7.24(2H,m),,7.46(1H,m),7.76(1H,m),7.86
(1H,d,J=3.0Hz),10.20(1H,s). IR(CHCl3):3465,3010,2924,1739,1604,1546,1504/cm. [α]D=+39.4゜(MeOH,c=1.01,22℃). m.p.167.0−168.0℃ No.2a−141 CDCl3 300MHz 0.99(1H,d,J=10.2Hz),1.14and1.24(each 3H,each
s),1.55−2.44(14H,m),3.84(3H,s),4.27(1H,m),
5.34−5.52(2H,m),6.28(1H,d,J=9.0Hz),6.91and7.
47(each 2H,each d,J=9.0Hz),6.98and7.14(each 1
H,each d,J=16.5Hz),7.54and7.70(each 2H,eachd,J
=8.7Hz). IR(CHCl3):3453,3025,3015,2925,2870,2839,1740,170
8,1649,1602,1510,1493,1470/cm. [α]D=+73.4゜(MeOH,c=1.02,22℃). m.p.155.0−157.0℃ No.2a−142 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.11and1.23(each 3H,each
s),1.52−2.45(14H,m),3.79(3H,s),4.27(1H,m),
5.34−5.50(2H,m),6.24(1H,d,J=9.0Hz),6.49and6.
62(each 1H,each d,J=12.3Hz),6.77and7.16(each 2
H,each d,J=8.7Hz),7.32and7.59(each 2H,eachd,J=
8.1Hz). IR(CHCl3):3453,3025,3014,2925,2870,2839,1739,170
8,1649,1606,1510,1494/cm. [α]D=+60.7゜(MeOH,c=0.99,22℃). No.2a−143 [α]D=+57.3゜(MeOH,c=1.01,23℃). No.2a−144 [α]D=+12.2゜(MeOH,c=1.00,23℃). m.p.114.0−126.0℃ No.2a−145 CDCl3 300MHz 0.95(1H,d,J=10.2Hz),1.10and1.21(each 3H,each
s),1.52−2.44(14H,m),4.25(1H,m),5.33−5.49(2
H,m),6.37(1H,d,J=8.7Hz),7.45−7.47(3H,m),7.6
2−7.66(2H,m),7.69and7.80(each 2H,each d,J=7.5
Hz). IR(CHCl3):3449,3058,3027,3012,2925,2870,1708,165
5,1513,1481,1043/cm. [α]D=+61.0゜(MeOH,c=1.01,23℃). No.2a−146 CDCl3 300MHz 0.95(1H,d,J=10.5Hz),1.09and1.21(each 3H,each
s),1.50−2.41(14H,m),4.25(1H,m),5.33−5.49(2
H,m),6.33(1H,d,J=8.4Hz),7.49−7.61(3H,m),7.9
1−7.92(2H,m),7.82and7.97(each 2H,each d,J=8.7
Hz). IR(CHCl3):3447,3029,3023,3015,2925,2870,1708,166
0,1514,1484,1321,1161/cm. [α]D=+62.0゜(MeOH,c=1.00,22℃). No.2a−147 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.12and1.23(each 3H,each
s),1.52−2.46(14H,m),2.51(3H,s),4.26(1H,m),
5.34−5.51(2H,m),6.23(1H,d,J=8.4Hz),7.26and7.
64(each 2H,each d,J=8.4Hz). IR(CHCl3):3453,3027,3015,2925,2870,2665,1708,164
8,1596,1516,1484/cm. [α]D=+67.7゜(MeOH,c=0.82,22℃). No.2a−148 [α]D=+72.5゜(MeOH,c=1.01,25℃). No.2a−149 [α]D=+67.8゜(MeOH,c=0.98,25℃). No.2a−150 CDCl3 300MHz 0.94(1H,d,J=10.2Hz),1.10and1.23(each 3H,each
s),1.52−2.50(14H,m),4.22(1H,m),5.36−5.55(2
H,m),6.48(1H,d,J=8.4Hz),8.35(1H,s),8.90(1H,
s). IR(CHCl3):3443,3374,3091,3024,3012,2925,2871,170
9,1652,1525,1494/cm. [α]D=+58.1゜(MeOH,c=1.01,23℃). m.p.120.0−122.0℃ No.2a−151 [α]D=+40.6゜(MeOH,c=1.01,23℃). No.2a−152 CDCl3 300MHz 0.96(1H,d,J=10.5Hz),1.10and1.24(each 3H,each
s),1.50−2.50(14H,m),2.71(3H,s),4.26(1H,m),
5.37−5.51(2H,m),6.02(1H,d,J=9.0Hz),8.73(1H,
s). IR(CHCl3):3463,3435,3087,3025,3014,2925,2870,170
8,1649,1523,1503/cm. [α]D=+54.1゜(MeOH,c=1.02,22℃). No.2a−153 CDCl3 300MHz 0.95(1H,d,J=9.9Hz),1.11and1.23(each 3H,each
s),1.50−2.50(14H,m),2.50(3H,s),4.26(1H,m),
5.36−5.51(2H,m),6.01(1H,d,J=8.4Hz),6.88(1H,
d,J=5.1Hz),7.26(1H,d,J=5.1Hz). IR(CHCl3):3469,3431,3025,3013,2925,2871,2664,170
8,1639,1544,1505/cm. [α]D=+35.8゜(MeOH,c=1.03,22℃). No.2a−154 CDCl3 300MHz 0.95(1H,d,J=9.9Hz),1.10and1.22(each 3H,each
s),1.52−2.46(14H,m),2.51(3H,d,J=1.2Hz),4.26
(1H,m),5.34−5.50(2H,m),6.00(1H,d,J=8.4Hz),
6.73(1H,dd,J=5.1and3.6Hz),7.29(1H,d,J=3.6H
z). IR(CHCl3):3450,3431,3026,3011,2925,2869,1739,170
8,1639,1547,1508/cm. [α]D=+50.5゜(MeOH,c=1.01,22℃). No.2a−155 CDCl3 300MHz 0.99(1H,d,J=10.2Hz),1.19and1.25(each 3H,each
s),1.53−2.48(14H,m),4.31(1H,m),5.36−5.51(2
H,m),6.79(1H,d,J=9.3Hz),7.29(1H,m),7.41(1H,
m),7.48(1H,s),7.51(1H,m),7.66(1H,d,J=8.1H
z). IR(CHCl3):3436,3029,3024,3015,2925,2871,2670,170
8,1659,1598,1510/cm. [α]D=+69.1゜(MeOH,c=1.01,22℃). No.2a−156 CDCl3:CD3OD=10:1 300MHz 0.99(1H,d,J=9.9Hz),1.11and1.21(each 3H,each
s),1.56−2.58(14H,m),4.22(1H,m),5.35−5.59(2
H,m),6.83(1H,d,J=8.4Hz),7.48(1H,d,J=8.4Hz),
7.61(1H,dd,J=1.5and8.4Hz),8.09(1H,d,J=1.5H
z),8.12(1H,s). IR(KBr):3422,3115,2985,2922,2869,2609,1708,1636,
1578,1529,1470/cm. [α]D=+62.8゜(MeOH,c=1.01,22℃). No.2a−157 [α]D=+40.0゜(MeOH,c=0.95,22℃). No.2a−158 CDCl3 300MHz 1.00(1H,d,J=10.5Hz),1.17and1.24(each 3H,each
s),1.54−2.50(14H,m),4.34(1H,m),5.36−5.52(2
H,m),7.80(1H,d,J=9.0Hz),9.30(1H,s). IR(CHCl3):3410,3122,3030,3012,2925,2871,2668,170
9,1667,1538,1466/cm. [α]D=+44.9゜(MeOH,c=0.99,22℃). No.2a−159 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.13and1.22(each 3H,each
s),1.55−2.43(14H,m),3.03(6H,s),4.23(1H,m),
5.32−5.51(2H,m),6.16(1H,d,J=8.7Hz),6.87and7.
63(each 2H,each d,J=8.7Hz). IR(CHCl3):3457,3028,3006,2924,2870,2654,1739,170
9,1637,1608,1608,1534,1501/cm. [α]D=+64.8゜(MeOH,c=1.01,22℃). No.2a−160 d6−DMSO 300MHz 0.83(1H,d,J=9.9Hz),1.02and1.19(each 3H,each
s),1.38−1.61(3H,m),1.90−2.32(11H,m),3.90(1
H,m),5.41−5.44(2H,m),7.32(1H,dd,J=0.9and7.2H
z),7.45−7.60(2H,m),7.77(1H,dd,J=0.9and7.8H
z),8.03(1H,d,J=6.9Hz),12.40(1H,s). IR(Nujol):3315,2924,2856,2656,2535,1737,1703,163
7,1598,1581,1541/cm. [α]D=+78.5゜(MeOH,c=1.01,24℃). m.p.161.0−162.0℃ No.2a−161 [α]D=+65.3゜(MeOH,c=1.00,22℃). No.2a−162 CDCl3 300MHz 0.99(1H,d,J=10.2Hz),1.13and1.25(each 3H,each
s),1.53−2.45(14H,m),4.30(1H,m),5.36−5.51(2
H,m),6.32(1H,d,J=8.4Hz),7.88and8.28(each 2H,e
ach d,J=9.0Hz). IR(CHCl3):3448,3029,3016,2925,2870,1708,1664,160
2,1527,1484,1347/cm. [α]D=+72.7゜(MeOH,c=1.02,22℃). No.2a−163 CDCl3 300MHz 0.96(1H,d,J=10.2Hz),1.11and1.23(each 3H,each
s),1.55−2.51(14H,m),4.26(1H,m),5.36−5.57(2
H,m),6.68(1H,d,J=7.8Hz),7.41(1H,dd,J=4.8and
8.1Hz),8.20(1H,d,J=8.1Hz),8.66(1H,d,J=4.8H
z),9.00(1H,s). IR(CHCl3):3448,3026,3013,2925,2870,2534,1709,165
8,1590,1515,1471/cm. [α]D=+71.3゜(MeOH,c=1.01,22℃). No.2a−164 [α]D=+40.8゜(MeOH,c=0.98,22℃). No.2a−165 CDCl3 300MHz 0.96(1H,d,J=10.5Hz),1.11and1.24(each 3H,each
s),1.55−2.52(14H,m),4.24(1H,m),5.37−5.57(2
H,m),6.63(1H,d,J=7.8Hz),7.59and8.63(each 2H,e
ach d,J=6.0Hz). IR(CHCl3):3447,3346,3028,3016,2925,2870,2538,194
1,1708,1662,1556,1516/cm. [α]D=+75.4゜(MeOH,c=1.01,22℃). No.2a−166 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.11and1.22(each 3H,each
s),1.51−2.44(14H,m),2.95(6H,s),4.25(1H,m),
5.33−5.50(2H,m),6.19(1H,d,J=8.7Hz),6.77and6.
97(each 2H,each d,J=8.4Hz),6.94and7.65(each 2
H,each d,J=9.0Hz). IR(CHCl3):3453,3024,3016,2924,2871,2806,1739,170
8,1647,1612,1604,1515,1490/cm. [α]D=+53.1゜(MeOH,c=1.02,23℃). m.p.104.0−105.5℃ No.2a−167 CDCl3 300MHz 1.01(1H,d,J=9.9Hz),1.19and1.26(each 3H,each
s),1.56−2.53(14H,m),4.37(1H,m),5.35−5.55(2
H,m),6.47(1H,d,J=8.4Hz),7.61−7.71(2H,m),7.7
9(2H,s),7.89−7.97(2H,m),8.27(1H,d,J=2.1H
z),8.66−8.73(2H,m). IR(CHCl3):3450,3024,3014,2925,2870,2667,1707,165
0,1531,1509/cm. [α]D=+70.5゜(MeOH,c=1.00,22℃). No.2a−168 CDCl3 300MHz 1.02(1H,d,J=10.2Hz),1.20and1.26(each 3H,each
s),1.56−2.50(14H,m),4.38(1H,m),5.36−5.56(2
H,m),6.51(1H,d,J=8.4Hz),7.61−7.93(7H,m),8.7
4(1H,d,J=8.4Hz),9.15(1H,s). IR(CHCl3):3517,3451,3060,3028,3011,2925,2870,266
4,1709,1651,1519,1498/cm. [α]D=+54.4゜(MeOH,c=1.00,23℃). No.2a−169 CDCl3 300MHz 0.96(1H,d,J=10.5Hz),1.09and1.21(each 3H,each
s),1.50−2.44(14H,m),3.85(3H,s),4.24(1H,m),
5.32−5.48(2H,m),6.19(1H,d,J=8.4Hz),6.94and7.
45(each 2H,each d,J=9.0Hz),7.11and7.45(each 2
H,each d,J=8.7Hz). IR(CHCl3):3516,3453,3029,3009,2925,2870,2840,266
5,1708,1650,1593,1515,1493,1482/cm. [α]D=+57.8゜(MeOH,c=1.00,23℃). No.2a−170 CDCl3 300MHz 0.98(1H,d,J=10.2Hz),1.15and1.24(each 3H,each
s),1.52−2.50(14H,m),4.28(1H,m),5.33−5.54(2
H,m),6.25(1H,d,J=8.2Hz),7.38−7.44(2H,m),7.7
4(1H,s),7.81−7.86(2H,m). IR(CHCl3):3517,3448,3427,3024,3013,2925,2870,266
9,1708,1650,1562,1535,1500/cm. [α]D=+61.6゜(MeOH,c=1.00,23℃). No.2a−171 CDCl3 300MHz 0.96(1H,d,J=10.2Hz,1.11and1.22(each 3H,each
s),1.52−2.42(14H,m),2.48(3H,s),4.21(1H,m),
5.31−5.52(2H,m),6.06(1H,d,J=8.2Hz),6.97and7.
59(each 1H,each d,J=1.2Hz). IR(CHCl3):3452,3113,3028,3007,2925,2870,2669,170
8,1645,1554,1509/cm. [α]D=+52.4゜(MeOH,c=1.00,23℃). No.2a−172 CDCl3 300MHz 0.96(1H,d,J=10.2Hz),1.09and1.28(each 3H,each
s),1.50−2.40(14H,m),2.69(3H,s),4.24(1H,m),
5.35−5.51(2H,m),5.96(1H,d,J=8.7Hz),7.03and7.
07(each 1H,each d,J=5.4Hz). IR(CHCl3):3451,3031,3013,2925,2870,2666,1708,164
7,1542,1497/cm. [α]D=+51.2゜(MeOH,c=1.00,23℃). No.2a−173 CDCl3 300MHz 0.95(1H,d,J=10.2Hz),1.10and1.23(each 3H,each
s),1.50−2.45(14H,m),4.22(1H,m),5.35−5.49(2
H,m),6.05(1H,d,J=8.4Hz),7.26and7.75(each 1H,e
ach d,J=1.5Hz). IR(CHCl3):3451,3011,3029,3011,2925,2870,1708,165
2,1538,1500/cm. [α]D=+50.6゜(MeOH,c=1.01,23℃). No.2a−174 CDCl3 300MHz 0.96(1H,d,J=10.2Hz),1.13and1.23(each 3H,each
s),1.52−2.50(14H,m),4.29(1H,m),5.35−5.51(2
H,m),7.02(1H,d,J=8.4Hz),7.32and8.16(each 1H,e
ach d,J=3.9Hz). IR(CHCl3):3417,3115,3023,3014,2925,2870,1708,164
5,1530/cm. [α]D=+48.8゜(MeOH,c=1.02,23℃). No.2a−175 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.14and1.23(each 3H,each
s),1.50−2.52(14H,m),2.52(3H,s),4.29(1H,m),
5.34−5.51(2H,m),7.78(1H,d,J=9.0Hz),7.24and7.
52(each 1H,each d,J=5.4Hz). IR(CHCl3):3329,3093,3023,3015,2924,2871,1708,164
0,1526/cm. [α]D=+45.0゜(MeOH,c=1.01,23℃). No.2a−176 CDCl3 300MHz 0.95(1H,d,J=10.5Hz),1.09and1.23(each 3H,each
s),1.52−2.46(14H,m),2.40(3H,d,J=0.9Hz),4.24
(1H,m),5.35−5.51(2H,m),6.05(1H,d,J=8.7Hz),
6.95(1H,m),7.57(1H,d,J=3.3Hz). IR(CHCl3):3517,3444,3103,3024,3013,2926,2870,173
9,1708,1649,1636,1507/cm. [α]D=+54.8゜(MeOH,c=1.01,23℃). m.p.97.0−99.0℃ No.2a−177 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.11and1.23(each 3H,each
s),1.52−2.45(14H,m),3.93(3H,s),4.27(1H,m),
5.34−5.50(2H,m),6.35(1H,d,J=3.3Hz),7.80(1H,
d,J=8.7Hz),8.10(1H,d,J=3.3Hz). IR(CHCl3):3395,3121,3031,3019,3012,2925,2871,173
9,1709,1640,1557,1533/cm. [α]D=+22.8゜(MeOH,c=1.01,23℃). m.p.109.0−112.0℃ No.2a−178 CDCl3 300MHz 0.96(1H,d,J=10.5Hz),1.10and1.23(each 3H,each
s),1.51−2.45(14H,m),4.24(1H,m),5.35−5.50(2
H,m),6.09(1H,d,J=8.4Hz),7.17−7.31(6H,m),7.9
5(1H,d,J=1.5Hz). IR(CHCl3):3510,3451,3062,3031,3022,3011,2925,287
0,2662,1708,1651,1582,15351497,1477/cm. [α]D=+47.9゜(MeOH,c=1.01,25℃). No.2a−179 CDCl3 300MHz 0.96(1H,d,J=10.2Hz),1.14and1.24(each 3H,each
s),1.52−2.48(14H,m),4.30(1H,m),5.36−5.52(2
H,m),6.73(1H,d,J=9.0Hz),6.26and7.37(each 1H,e
ach d,J=6.0Hz). IR(CHCl3):3509,3429,3115,3094,3025,3014,2925,287
1,2666,1708,1649,1529,1510/cm. [α]D=+51.0゜(MeOH,c=1.02,25℃). No.2a−180 CDCl3 300MHz 0.95(1H,d,J=10.2Hz),1.14and1.24(each 3H,each
s),1.52−2.46(14H,m),3.89(3H,s),4.21(1H,m),
5.35−5.50(2H,m),6.05(1H,d,J=8.4Hz),6.46and7.
04(each 1H,each d,J=1.8Hz). IR(CHCl3):3516,3450,3114,3031,3010,2925,2871,170
8,1648,1546,1511,1477/cm. [α]D=+49.1゜(MeOH,c=1.01,25℃). No.2a−181 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.14and1.23(each 3H,each
s),1.52−2.48(14H,m),2.42(3H,s),4.31(1H,m),
5.34−5.52(2H,m),8.07(1H,d,J=9.3Hz),7.27and8.
17(each 1H,each d,J=3.3Hz). IR(CHCl3):3510,3301,3112,3023,3007,2924,2871,266
3,1708,1636,1534/cm. [α]D=+41.0゜(MeOH,c=0.96,25℃). No.2a−182 CDCl3 300MHz 0.96(1H,d,J=10.2Hz),1.11and1.23(each 3H,each
s),1.53−2.46(14H,m),2.51(3H,s),4.21(1H,m),
5.35−5.51(2H,m),6.05(1H,d,J=8.1Hz),7.26and7.
78(each 1H,each d,J=1.8Hz). IR(CHCl3):3509,3450,3109,3024,3012,2925,2870,266
6,1708,1650,1535,1498,1471/cm. [α]D=+52.9゜(MeOH,c=0.95,25℃). No.2a−183 CDCl3 300MHz 0.96(1H,d,J=10.5Hz),1.12and1.22(each 3H,each
s),1.52−2.46(14H,m),4.25(1H,m),5.33−5.51(2
H,m),6.17(1H,d,J=8.7Hz),7.01−7.05(3H,m),7.1
4and7.62(each 2H,each d,J=8.7Hz),7.27−7.34(2
H,m). IR(CHCl3):3428,3026,3015,2925,2870,2666,1739,170
8,1643,1613,1594,1526,1499/cm. [α]D=+64.8゜(MeOH,c=1.02,23℃). No.2a−184 CDCl3 300MHz 1.01(1H,d,J=10.2Hz),1.18and1.26(each 3H,each
s),1.55−2.50(14H,m),4.35(1H,m),5.35−5.55(2
H,m),6.42(1H,t,J=8.7Hz),7.46−7.52(2H,m),7.7
3(1H,dd,J=1.8and8.4Hz),7.83−7.89(2H,m),8.21
(1H,m),8.59(1H,d,J=1.5Hz). IR(CHCl3):3451,3031,3014,2925,2870,2660,1739,170
8,1650,1604,1513,1463/cm. [α]D=+58.3゜(MeOH,c=1.00,23℃). No.2a−185 CDCl3 300MHz 1.00(1H,d,J=10.2Hz),1.18and1.25(each 3H,each
s),1.55−2.50(14H,m),4.34(1H,m),5.35−5.54(2
H,m),6.36(1H,d,J=8.7Hz),7.37(1H,d,J=7.4Hz),
7.50(1H,m),7.57−7.59(2H,m),7.79(1H,dd,J=1.8
and8.1Hz),7.99(1H,d,J=7.8Hz),8.39(1H,d,J=1.8
Hz). IR(CHCl3):3451,3030,3020,2870,2665,1708,1652,163
2,1603,1586,1514,1469,1448/cm. [α]D=+59.4゜(MeOH,c=1.01,24℃). No.2a−186 CDCl3 300MHz 1.00(1H,d,J=10.5Hz),1.17and1.25(each 3H,each
s),1.54−2.50(14H,m),4.33(1H,m),5.35−5.54(2
H,m),6.37(1H,d,J=8.7Hz),7.37(1H,d,J=7.4Hz),
7.51(1H,d,J=7.8Hz),7.56(1H,m),7.70(1H,dd,J=
1.2and8.4Hz),7.97(3H,m). IR(CHCl3):3451,3030,3014,2924,2870,2671,1739,170
8,1652,1577,1517,1488,1471/cm. [α]D=+72.2゜(MeOH,c=1.00,24℃). No.2a−187 CDCl3 300MHz 1.00(1H,d,J=9.8Hz),1.18and1.25(each 3H,each
s),1.54−2.53(14H,m),4.07(3H,s),4.37(1H,m),
5.30−5.54(2H,m),7.34(1H,m),7.47(1H,s),7.47
−7.60(2H,m),7.93(1H,d,J=7.8Hz),8.43(1H,s),
8.49(1H,d,J=9.0Hz). IR(CHCl3):3397,3074,3027,3020,3009,2924,1738,170
8,1647,1633,1534,1465,1453/cm. [α]D=+43.7゜(MeOH,c=1.01,25℃). No.2a−188 CDCl3 300MHz 0.97(1H,d,J=10.2Hz),1.11and1.23(each 3H,each
s),1.53−2.50(14H,m),4.23(1H,m),5.37−5.50(2
H,m),6.10(1H,d,J=9.0Hz),6.20(1H,m),6.51(1H,
m),6.97(1H,m),10.81(1H,bs). IR(CHCl3):3450,3236,3112,3029,3015,2925,2871,264
5,1701,1616,1558,1516/cm. [α]D=+50.6゜(MeOH,c=1.01,24℃). No.2a−189 CDCl3 300MHz 0.94(1H,d,J=9.9Hz),1.11and1.23(each 3H,each
s),1.50−2.46(14H,m),3.93(3H,s),4.18(1H,m),
5.35−5.52(2H,m),6.03(1H,d,J=9.3Hz),6.09(1H,
m),6.48(1H,m),6.73(1H,m). IR(CHCl3):3452,3102,3028,3007,2925,2871,2666,173
9,1708,1650,1536,1499,1471/cm. [α]D=+49.8゜(MeOH,c=1.01,23℃). m.p.101.5−103.5℃ No.2a−190 CDCl3 300MHz 0.94(1H,d,J=10.2Hz),1.11and1.21(each 3H,each
s),1.54−2.47(14H,m),4.23(1H,m),5.33−5.52(2
H,m),6.06(1H,d,J=9.0Hz),6.34(1H,m),6.75(1H,
m),6.36(1H,m),9.71(1H,bs). IR(CHCl3):3470,3215,3030,3020,3010,2925,2871,266
4,1709,1613,1564,1510/cm. [α]D=+43.3゜(MeOH,c=1.01,24℃). No.2a−191 CDCl3 300MHz 0.96(1H,d,J=10.2Hz),1.11and1.22(each 3H,each
s),1.55−2.44(14H,m),3.66(3H,s),4.20(1H,m),
5.35−5.51(2H,m),5.93(1H,d,J=8.4Hz),6.27(1H,
dd,J=1.8and2.7Hz),6.56(1H,d,J=2.7Hz),7.19(1
H,d,J=1.8Hz). IR(CHCl3):3452,3031,3018,3006,2925,2871,2662,173
6,1710,1634,1609,1556,1498/cm. [α]D=+43.1゜(MeOH,c=1.01,23℃). No.2a−192 CDCl3 300MHz 0.96(1H,d,J=10.5Hz),1.11and1.21(each 3H,each
s),1.43(3H,t,J=7.5Hz),1.54−2.44(14H,m),3.93
(1H,q,J=7.5Hz),4.21(1H,m),5.33−5.51(2H,m),
5.94(1H,d,J=8.4Hz),6.27(1H,dd,J=1.8and2.7H
z),6.62(1H,d,J=2.7Hz),7.26(1H,t,J=1.8Hz). IR(CHCl3):3630,3452,3032,3018,3006,2925,2871,266
1,1735,1710,1633,1610,1555,1497/cm. [α]D=+40.1゜(MeOH,c=1.00,23℃). No.2a−193 CDCl3 300MHz 0.95(1H,d,J=10.2Hz),1.10and1.22(each 3H,each
s),1.53−2.49(14H,m),2.58(3H,s),4.21(1H,m),
5.35−5.54(2H,m),6.15(1H,d,J=8.1Hz),6.52(1H,
dd,J=1.8and3.6Hz),7.29(1H,t,J=3.6Hz),7.94(1
H,t,J=1.8Hz). IR(CHCl3):3516,3450,3410,3152,3027,3015,2925,287
1,2670,1732,1648,1574,1509/cm. [α]D=+45.0゜(MeOH,c=1.01,25℃). No.2a−194 CDCl3 300MHz 0.99(1H,d,J=10.2Hz),1.11and1.24(each 3H,each
s),1.52−2.53(14H,m),4.34(1H,m),5.33−5.57(2
H,m),6.21(1H,d,J=8.6Hz),7.35−7.50(2H,m),7.8
3(1H,s),7.86(1H,m),8.31(1H,m). IR(CHCl3):3443,3067,3013,2925,2870,2665,1708,165
1,1515,1493/cm. [α]D=+55.7゜(MeOH,c=1.01,23℃). No.2a−195 CDCl3 300MHz 1.01(1H,d,J=10.0Hz),1.06and1.26(each 3H,each
s),1.50−2.64(14H,m),2.68(3H,s),4.40(1H,m),
5.36−5.61(2H,m),6.02(1H,d,J=9.4Hz),7.30−7.4
2(2H,m),7.73−7.86(2H,m). IR(CHCl3):3510,3434,3062,3029,3014,2924,2871,266
9,1708,1650,1563,1539,1500/cm. [α]D=+72.4゜(MeOH,c=1.00,23℃). m.p.111.0−112.0℃ No.2a−196 CDCl3 300MHz 0.42and1.04(each 3H,each s),0.80(1H,d,J=10.0H
z),1.11−2.48(14H,m),2.24(3H,s),4.02(1H,m),
5.23−5.44(2H,m),5.53(1H,d,J=8.8Hz),7.27−7.3
1(2H,m),7.42−7.48(3H,m),7.93(1H,s). IR(CHCl3):3419,3114,3025,3006,2924,2871,2662,173
7,1709,1636,1540,1519/cm. [α]D=+43.7゜(MeOH,c=1.01,23℃). No.2a−197 CDCl3 300MHz 0.95(1H,d,J=10.0Hz),1.09and1.23(each 3H,each
s),1.54−2.46(18H,m),2.77(4H,bs),4.21(1H,
m),5.32−5.54(2H,m),6.02(1H,d,J=8.6Hz),7.43
(1H,s). IR(CHCl3):3445,3101,3024,3014,2928,2865,2661,173
9,1708,1646,1550,1507/cm. [α]D=+51.9゜(MeOH,c=1.01,23℃). No.2a−198 CDCl3 300MHz 0.96(1H,d,J=10.2Hz),1.11and1.22(each 3H,each
s),1.50−2.44(14H,m),4.24(1H,m),4.42(2H,s),
5.35−5.49(2H,m),6.25(1H,d,J=8.1Hz),7.33(1H,
m),7.43(1H,dd,J=1.5and7.5Hz),7.49(1H,d,J=8.1
Hz),7.60−7.63(1H,m),7.68(1H,dd,J=1.8and7.8H
z),8.02(1H,d,J=1.8Hz),8.19(1H,dd,J=1.5and8.1
Hz). IR(CHCl3):3448,3030,3012,2925,2870,1739,1708,167
1,1588,1559,1514,1472/cm. [α]D=+56.9゜(MeOH,c=1.01,24℃). No.2a−199 CDCl3 300MHz 0.96(1H,d,J=10.2Hz),1.11and1.22(each 3H,each
s),1.51−2.46(14H,m),3.40(1H,m),3.76(1H,m),
4.24(1H,m),5.33−5.51(2H,m),6.25(1H,m),7.16
(1H,m),7.24−7.33(2H,m),7.46(1H,d,J=7.5Hz),
7.52−7.60(2H,m),7.85(1H,dd,J=1.8and4.5Hz). IR(CHCl3):3583,3447,3062,3028,3013,2924,2871,266
3,1708,1651,1600,1557,1514,1471/cm. [α]D=+54.8゜(MeOH,c=1.00,23℃). No.2a−200 CDCl3 300MHz 0.96(1H,d,J=10.2Hz),1.12and1.23(each 3H,each
s),1.51−2.46(14H,m),4.25(1H,m),5.34−5.51(2
H,m),6.25(1H,d,J=8.4Hz),7.02and7.10(each 1H,e
ach d,J=12.3Hz)7.23−7.33(4H,m),7.50(1H,m),
7.64(1H,dd,J=1.8and7.8Hz),7.82(1H,d,J=1.8H
z). IR(CHCl3):3450,3060,3025,3014,2925,2871,2662,170
8,1653,1596,1542,1513,1473/cm. [α]D=+62.5゜(MeOH,c=1.00,24℃). No.2a−201 CDCl3 300MHz 0.95(1H,d,J=9.9Hz),1.15and1.22(each 3H,each
s),1.55−2.60(14H,m),4.26(1H,m),5.35−5.63(2
H,m),7.14(1H,d,J=9.9Hz),7.34and7.40(each 1H,e
ach d,J=1.29Hz),7.62−7.73(4H,m),8.25−8.30(2
H,m),8.72(1H,d,J=1.5Hz). IR(CHCl3):3443,3389,3297,3061,3030,3016,2925,287
0,1726,1708,1652,1603,1521,1483,1472,1309/cm. [α]D=+61.1゜(MeOH,c=1.01,23℃). No.2a−202 CDCl3 300MHz 0.96(1H,d,J=10.2Hz),1.09and1.22(each 3H,each
s),1.52−2.43(14H,m),2.63(3H,s),4.25(1H,m),
5.33−5.49(2H,m),6.19(1H,d,J=8.4Hz),7.10and7.
58(each 2H,each d,J=9.0Hz),7.21(1H,m),7.30−
7.32(2H,m),7.46(1H,d,J=7.5Hz). IR(CHCl3):3511,3453,3062,3032,3014,2925,2870,173
9,1708,1650,1595,1556,1516,1482,1471/cm. [α]D=+60.2゜(MeOH,c=1.01,25℃). No.2a−203 CDCl3 300MHz 0.96(1H,d,J=10.5Hz),1.09and1.23(each 3H,each
s),1.52−2.43(14H,m),4.23(1H,m),5.35−5.51(2
H,m),5.93(1H,d,J=8.7Hz),6.56(1H,dd,J=0.9and
1.8Hz),7.43(1H,t,J=1.8Hz),7.92(1H,dd,J=0.9an
d1.8Hz). IR(CHCl3):3517,3450,3134,3031,3008,2925,2870,266
7,1708,1656,1588,1570,1514/cm. [α]D=+46.7゜(MeOH,c=0.92,25℃). No.2b−1 [α]D=+25.6゜(MeOH,c=1.01,23℃). No.2b−2 [α]D=+38.9゜(MeOH,c=1.01,24℃). No.2c−1 [α]D=+60.5゜(MeOH,c=1.01,22℃). No.2c−2 [α]D=+55.8゜(MeOH,c=0.92,22℃). No.2c−3 [α]D=+54.7゜(MeOH,c=1.01,22℃). No.2d−1 [α]D=−6.2゜(MeOH,c=1.00,21℃). No.2d−2 [α]D=+15.8゜(MeOH,c=0.34,22℃). No.2d−3 [α]D=+31.6゜(MeOH,c=1.01,22℃). No.2e−1 [α]D=−9.4゜(MeOH,c=1.00,22℃). No.2e−2 [α]D=−1.8゜(MeOH,c=1.02,23℃). No.2e−3 [α]D=−6.7゜(MeOH,c=1.01,23℃). No.2f−1 [α]D=+6.8゜(MeOH,c=1.01,23℃). No.2f−2 [α]D=−2.6゜(MeOH,c=1.00,22℃). No.2f−3 [α]D=−3.5゜(MeOH,c=1.01,22℃). No.2g−1 [α]D=+54.6゜(MeOH,c=1.01,24℃). No.3a−2 CDCl3 300MHz 0.98−2.15(14H,m),2.31(2H,t,J=7.2Hz),2.35−2.
40(1H,m),3.10−3.20(1H,m),5.00(1H,d,J=6.9H
z),5.30−5.48(2H,m),6.75(1H,d,J=10.2Hz),7.38
−7.52(6H,m). IR(CDCl3):3266,3028,2954,2874,1709,1620,1448,141
2,1318,1141,970,892/cm. [α]D=+20.3±0.6゜(CHCl3,c=1.05,24℃). No.3a−3 CDCl3 300MHz 0.95−2.00(14H,m),2.20−2.29)(3H,m),3.00−3.0
8(1H,m),3.66−(3H,s),5.00(1H,d,J=6.6Hz),5.1
3−5.29(2H,m),7.38−7.52(3H,m),7.59−7.65(2H,
m).7.69−7.75(2H,m),7.92−7.98(2H,m). IR(CHCl3):3376,3018,2946,2868,1727,1594,1436,139
5,1322,1157,1095,890/cm. [α]D=+2.3±0.4゜(CHCl3,c=1.03,22℃). mp.65−66.5℃ No.3a−4 CDCl3 300MHz 0.93−2.05(14H,m),2.15−2.22(1H,m),2.31(2H,t,
J=7.2Hz),3.01−3.10(1H,m),5.18−5.31(3H,m),
7.38−7.52(3H,m),7.58−7.66(2H,m),7.69−7.76
(2H,m),7.92−7.98(2H,m) IR(CHCl3):3374,3260,3020,2948,2868,1708,1594,147
9,1396,1319,1156,1095,1052,891/cm. [α]D=+13.1±0.5゜(CHCl3,c=1.16,24℃). No.3a−6 CD3OD 300MHz 1.04−1.95(14H,m),2.07(2H,t,J=7.8Hz),2.14−2.
22(1H,m),2.94−3.00(1H,m),5.04−5.25(2H,m),
7.36−7.52(3H,m),7.66−7.71(2H,m),7.78−7.85
(2H,m),7.91−7.97(2H,m). IR(KBr):3421,3278,2951,2872,1562,1481,1409,1317,
1156,1097,1057,895/cm. [α]D=−15.3±0.5゜(CHCl3,c=1.06,23℃). mp.105−112℃ No.3a−11 CDCl3 300MHz 0.90−2.04(14H,m),2.08−2.19(1H,m),2.35(2H,t,
J=7.2Hz),2.95−3.04(1H,m),5.17−5.32(3H,m),
7.56−7.63(2H,m),7.83−7.95(2H,m). IR(CHCl3):3260,3020,2948,2868,1707,1569,1456,138
3,1325,1268,1160,1088,1053,1006,892/cm. [α]D=+8.3±0.5゜(CHCl3,c=1.00,22℃). No.3a−16 CDCl3 300MHz 0.80−1.90(14H,m),1.98−2.04(1H,m),2.27(2H,t,
J=7.2Hz),2.88(6H,s),2.90−2.98(1H,m),4.88−
5.00(2H,m),5.13(1H,d,J=7.2Hz),7.18(1H,d,J=
7.5Hz),7.48−7.60(2H,m),8.25−8.33(2H,m),8.53
(1H,d,J=8.7Hz). IR(CHCl3):3272,3020,2946,2866,2782,1708,1573,145
5,1407,1311,1229,1160,1142,1070,942,891/cm. [α]D=−19.7±0.6゜(CHCl3,c=1.08,23.5℃). No.3a−31 CDCl3 300MHz 0.80−1.85(14H,m),2.02−2.08(1H,m),2.20(2H,t,
J=7.2Hz),2.85−2.95(1H,m),3.68(3H,s),4.80−
4.92(2H,m),4.96(1H,d,J=6.9Hz),7.50−7.70(3H,
m),7.92−7.98(1H,m),8.07(1H,d,J=8.4Hz),8.29
(1H,dd,J=1.5&7.5Hz),8.65(1H,d,J=8.7Hz). IR(CHCl3):3374,3016,2946,2868,1727,1506,1435,131
8,1160,1133,1105,1051,984,890/cm. [α]D=−39.3±0.8゜(CHCl3,c=1.07,22℃). No.3a−32 CDCl3 300MHz 0.80−1.90(14H,m),1.95−2.05(1H,m),2.27(2H,t,
J=7.2Hz),2.90−2.96(1H,m),4.85−5.00(2H,m),
5.23(1H,d,J=6.6Hz),7.50−7.72(3H,m),7.95(1H,
d,J=8.1Hz),8.07(1H,d,J=8.4Hz),8.29(1H,dd,J=
1.2&7.5Hz),8.66(1H,d,J=9.0Hz). IR(CHCl3):3270,3020,2948,2868,1708,1455,1412,131
7,1159,1132,1104,1079,1051,983,891/cm. [α]D=−29.2±0.6゜(CHCl3,c=1.08,22℃). No.3a−33 CD3OD 300MHz 0.94−1.84(14H,m),1.96−2.08(3H,m),2.77−2.84
(1H,m),4.67−4.84(2H,m),7.55−7.75(3H,m),8.0
2(1H,d,J=7.8Hz),8.12−8.26(2H,m),8.74(1H,d,J
=8.7Hz). IR(KBr):3432,3298,2951,2872,1564,1412,1315,1159,
1134,1107,1082,1058,986/cm. [α]D=−79.9±1.2゜(CH3OH,c=1.00,23℃). No.3a−34 CDCl3 300MHz 0.97−1.91(14H,m),2.13−2.20(1H,m),2.42(2H,t,
J=7.2Hz),3.00−3.07(1H,m),5.06−5.24(2H,m),
5.33(1H,d,J=6.9Hz),7.57−7.68(2H,m),7.82−8.0
0(4H,m),8.45(1H,d,J=1.2Hz) IR(CHCl3):3260,3020,2948,1708,1408,1319,1154,112
9,1073,953,893/cm. [α]D=+20.7±0.6゜(CHCl3,c=1.07,22℃). No.3a−35 CD3OD 300MHz 1.03−2.20(m,17H),2.97(m,1H),5.02(m,2H),7.64
(m,2H),8.00(m,4H),8.43(S,1H). IR(KBr):3360,3285,1562,1407,1316,1153,1130,1075/
cm. [α]D=≒0 [α]365=+20.9±0.6゜(CH3OH,c=1.04,23℃). No.3d−1 CDCl3 300MHz 0.93−2.55(m,17H),3.02(m,1H),5.24(m,2H),6.48
(m,1H),7.35−7.60(m,3H),7.85−8.00(m,2H) IR(Nujol):3275,1548,1160,1094,758,719,689,591,55
7/cm. [α]D=+19.0±0.6゜(CH3OH,c=1.010,26.5℃). 元素分析(C20H26NO4S.1/2Ca・1.0H2Oとして) 計算値:C.57,94;H,6.82;N,3.38;Ca,4.83;H2O,4.35 実測値:C.57,80;H,6.68;N,3.68;Ca,5.06;H2O,4.50 No.3d−6 [α]D=−20.7±0.6゜(CHCl3,c=1.00,24℃). No.3d−7 [α]D=−32±0.4゜(CHCl3,c=1.03,22℃). mp.65−67℃ No.3d−8 [α]D=−14.5±0.5゜(CHCl3,c=1.07,24℃). No.3d−9 [α]D=−12.2±0.5゜(CH3OH,c=1.00,23℃). mp.119−125℃ No.3d−10 [α]D=+39.7±0.8゜(CHCl3,c=1.07,22℃). No.3d−11 [α]D=+29.2±0.7゜(CHCl3,c=1.06,22℃). No.3d−12 [α]D=+76.4±1.1゜(CH3OH,c=1.03,24℃). No.3d−14 [α]D=−20.6±0.6゜(CHCl3,c=1.07,22℃). No.3d−15 [α]365=−28.0±0.7゜(CH3OH,c=1.03,24.5℃). No.3d−16 [α]D=−8.7±0.5゜(CHCl3,c=1.06,22℃). No.3d−17 CDCl3 300MHz 0.80−2.15(m,24H),2.32(t,J=7Hz,2H),2.68(t,J
=7Hz,2H),3.02(m,1H),2.15(m,24H),2.32(t,J=7
Hz,2H),2.68(t,J=7Hz,2H),3.02(m,1H),5.22(m,2
H),5.38(d,J=7Hz,1H),7.30(A2B2q−Apart,J=8Hz,
2H),7.81(A2B2qBpart,J=8Hz,2H),9.86(br.s,1
H). [α]D=≒0 [α]365=−9.7±0.5゜(CHCl3,c=1.03,22℃). No.3d−24 [α]D=+19.2±0.6゜(CHCl3,c=1.05,23℃). No.3d−26 CD3OD 300MHz 0.90−2.20(20H,m),2.88(1H,m),3.07(2H,q,J=7.0
Hz),5.00−5.40(2H,m),7.20−7.60(4H,m),7.95(1
H,m). IR(KBr):3415,3254,1698,1564,1314,1154/cm. No.3d−28 CD3OD 300MHz 0.90−2.20(20H,m),2.73(1H,q,J=7.0Hz),2.93(1
H,m),5.00−5.30(2H,m),7.40−7.50(2H,m),7.60−
7.77(2H,m). IR(KBr):3435,3280,1562,1323,1304,1151/cm. No.3d−30 元素分析C20H25BrNO4SNa Calc.C50.21;H5.27;Br16.70;N2.93;S6.70;Na4.81 found.C50.22;H5.40;Br15.57;N2.88;S6.41;Na5.10 IR(KBr):3425,3280,3085,1697,1570,1410,1321,1165,
1155/cm. No.3e−1 CD3OD 300MHz 0.71(1H,d,J=10.2Hz),1.04(3H,s),1.12(3H,s),
1.35−2.28(14H,m),2.24(3H,s),3.17−3.25(1H,
m),5.18−5.39(2H,m),7.37(2H,d,J=8.4Hz),7.75
(2H,d,J=8.4Hz). IR(CHCl3):3400,3289,2986,2924,2870,1559,1424,132
2,1305,1160,1095,1075,1030/cm. [α]D=+25.9±0.7゜(CH3OH,c=1.00,23℃). 上記実施例で得た化合物につき、以下の実験例に示す
方法で、インビボ及びインビトロ活性を試験した。
実験例1 PGD2受容体の結合実験 試験材料及び試験方法 (1)ヒト血小板膜画分の調製 健常人(成人男性及び女性)の静脈より3.8%クエン
酸ナトリウムの入ったプラスチック製シリンジにて採血
した血液をプラスチック製試験管に入れ、軽く転倒混和
した後、室温で、1800rpm、10分間遠心分離し、上清の
多血小板血漿[PRP(Platelet rich plasma)]を採取
した。このPRPをさらに室温、2300rpm、22分間の遠心分
離に付し、血小板を得た。得られた血小板はhomogenize
r(Ultra−Turrax)を用いてホモジナイズした後、4
℃、2000rpm、10分間遠心分離を3回行った、血小板膜
画分を得た。膜画分は蛋白定量後、2mg/mlとし、結合実
験に供するまで−80℃で冷凍保存した。
酸ナトリウムの入ったプラスチック製シリンジにて採血
した血液をプラスチック製試験管に入れ、軽く転倒混和
した後、室温で、1800rpm、10分間遠心分離し、上清の
多血小板血漿[PRP(Platelet rich plasma)]を採取
した。このPRPをさらに室温、2300rpm、22分間の遠心分
離に付し、血小板を得た。得られた血小板はhomogenize
r(Ultra−Turrax)を用いてホモジナイズした後、4
℃、2000rpm、10分間遠心分離を3回行った、血小板膜
画分を得た。膜画分は蛋白定量後、2mg/mlとし、結合実
験に供するまで−80℃で冷凍保存した。
(2)PGD2受容体の結合実験 結合反応液(50mM Tris/HCl,pH7.4,5mM MgCl2)0.2ml
に、ヒト血小板膜画分(0.1mg)及び5nM[3H]PGD2(11
5Ci/mmol)を加え、4℃で90分間反応させた。反応後ガ
ラス繊維濾紙を用いて濾過し、冷生理食塩水で数回洗浄
し、濾紙に残った放射活性を測定した。特異的結合量は
全結合量から非特異的結合量(10μΜ PGD2存在下での
結合量)を差し引いた値とした。各化合物の結合阻害活
性は、化合物非存在下での結合量を100%とし、各化合
物存在下での結合量(%)を求めて置換曲線を作成する
ことにより、50%抑制濃度(IC50値)を算出した。結果
を以下に示す。
に、ヒト血小板膜画分(0.1mg)及び5nM[3H]PGD2(11
5Ci/mmol)を加え、4℃で90分間反応させた。反応後ガ
ラス繊維濾紙を用いて濾過し、冷生理食塩水で数回洗浄
し、濾紙に残った放射活性を測定した。特異的結合量は
全結合量から非特異的結合量(10μΜ PGD2存在下での
結合量)を差し引いた値とした。各化合物の結合阻害活
性は、化合物非存在下での結合量を100%とし、各化合
物存在下での結合量(%)を求めて置換曲線を作成する
ことにより、50%抑制濃度(IC50値)を算出した。結果
を以下に示す。
実験例2 ヒト血小板を使ったPGD2受容体の拮抗活性 あらかじめ1/9量のクエン酸−デキストロース液を添
加したシリンジで健常人から末梢血を採取し、180gで10
分間遠心した後、上清(PRP:platelet rich plasma)を
採取する。得られたPRPを洗浄バッファーで3回遠心洗
浄した後、血小板数をミクロセルカウンターでカウント
する。最終濃度5×108個/mlとなるように調製した血小
板浮遊液を37℃に加温後、3−イソブチル−1−メチル
キサンチン(0.5mΜ)で5分間前処置し、種々の濃度に
希釈した化合物を添加し、その10分間に0.1〜2.0μΜの
PGD2を添加して反応を惹起した。15分後に塩酸を加えて
反応を停止し、超音波ホモジナイザーにて血小板を破壊
し、遠心後その上清中のcAMPを放射アッセイに定量す
る。薬物のPGD2受容体拮抗活性はPGD2添加によって増加
したcAMP量に対する抑制率を各濃度で求め、50%の阻害
を示す薬物濃度を算出して評価した。結果を以下に示
す。化合物番号 ヒト血小板cAMP上昇阻害IC50(μΜ) 3a−16 0.37 1a−121 2.11 1a−28 0.30 1a−47 2.09 2a−2 0.77 2a−4 0.94 2a−35 1.52 2a−75 0.71 実験例3 鼻閉モデルによる実験 モルモットを用いる鼻腔抵抗の測定及び抗鼻閉作用の
評価の方法を以下に示す。1%卵白アルブミン(OVA)
溶液を超音波ネブライザーでエアロゾル化し、これをハ
ートレイ(Hartley)系雄性モルモットに1週間隔で2
回、各10回分間吸入させて感作し、その7日後に抗原を
暴露して反応を惹起した。ペントバルビタール(30mg/k
g,i.p.)麻酔下にモルモットの気管を切開して鼻腔側と
肺側にそれぞれカニューレを装着し、肺側には毎分60
回、1回4mlの空気を送気する人工呼吸器を接続した。
ガラミン(2mg/kg,i.v.)でモルモットの自発呼吸を停
止させた後、鼻腔側のカニューレより人工呼吸器を用い
て毎分70回、1回4mlの空気を鼻吻側に送り、この送気
に必要な空気圧を側枝に装着したトランスデューサーを
介して測定し、鼻腔抵抗の指標とした。抗原の暴露は3
%OVA溶液のエアロゾルを人工呼吸器と鼻腔カニューレ
の間に3分間発生させることにより行った。被検薬物は
抗原暴露の10分前に静注した。成績は0から30分間の鼻
腔抵抗を連続的に測定し、その30分間のAUC(縦軸に鼻
腔抵抗(cmH2O)、横軸に時間(0〜30分間))を指標
に、ビークルに対する抑制率として表示した。結果を以
下に示す。
加したシリンジで健常人から末梢血を採取し、180gで10
分間遠心した後、上清(PRP:platelet rich plasma)を
採取する。得られたPRPを洗浄バッファーで3回遠心洗
浄した後、血小板数をミクロセルカウンターでカウント
する。最終濃度5×108個/mlとなるように調製した血小
板浮遊液を37℃に加温後、3−イソブチル−1−メチル
キサンチン(0.5mΜ)で5分間前処置し、種々の濃度に
希釈した化合物を添加し、その10分間に0.1〜2.0μΜの
PGD2を添加して反応を惹起した。15分後に塩酸を加えて
反応を停止し、超音波ホモジナイザーにて血小板を破壊
し、遠心後その上清中のcAMPを放射アッセイに定量す
る。薬物のPGD2受容体拮抗活性はPGD2添加によって増加
したcAMP量に対する抑制率を各濃度で求め、50%の阻害
を示す薬物濃度を算出して評価した。結果を以下に示
す。化合物番号 ヒト血小板cAMP上昇阻害IC50(μΜ) 3a−16 0.37 1a−121 2.11 1a−28 0.30 1a−47 2.09 2a−2 0.77 2a−4 0.94 2a−35 1.52 2a−75 0.71 実験例3 鼻閉モデルによる実験 モルモットを用いる鼻腔抵抗の測定及び抗鼻閉作用の
評価の方法を以下に示す。1%卵白アルブミン(OVA)
溶液を超音波ネブライザーでエアロゾル化し、これをハ
ートレイ(Hartley)系雄性モルモットに1週間隔で2
回、各10回分間吸入させて感作し、その7日後に抗原を
暴露して反応を惹起した。ペントバルビタール(30mg/k
g,i.p.)麻酔下にモルモットの気管を切開して鼻腔側と
肺側にそれぞれカニューレを装着し、肺側には毎分60
回、1回4mlの空気を送気する人工呼吸器を接続した。
ガラミン(2mg/kg,i.v.)でモルモットの自発呼吸を停
止させた後、鼻腔側のカニューレより人工呼吸器を用い
て毎分70回、1回4mlの空気を鼻吻側に送り、この送気
に必要な空気圧を側枝に装着したトランスデューサーを
介して測定し、鼻腔抵抗の指標とした。抗原の暴露は3
%OVA溶液のエアロゾルを人工呼吸器と鼻腔カニューレ
の間に3分間発生させることにより行った。被検薬物は
抗原暴露の10分前に静注した。成績は0から30分間の鼻
腔抵抗を連続的に測定し、その30分間のAUC(縦軸に鼻
腔抵抗(cmH2O)、横軸に時間(0〜30分間))を指標
に、ビークルに対する抑制率として表示した。結果を以
下に示す。
製剤例1 錠剤の製造 40mgの有効成分を含有する錠剤を常法により製造し
た。40mg錠の組成を以下に示す。
た。40mg錠の組成を以下に示す。
製剤例2 顆粒剤の製造
フロントページの続き (51)Int.Cl.7 識別記号 FI A61K 31/352 A61K 31/352 31/357 31/357 31/36 31/36 31/38 31/38 31/381 31/381 31/403 31/403 31/404 31/404 31/41 31/41 31/4164 31/4164 31/42 31/42 31/423 31/423 31/4245 31/4245 31/426 31/426 31/433 31/433 31/4402 31/4402 31/4406 31/4406 31/4409 31/4409 31/473 31/473 31/5375 31/5375 31/5415 31/5415 31/63 31/63 31/655 31/655 31/66 31/66 A61P 11/02 A61P 11/02 11/06 11/06 27/16 27/16 29/00 29/00 37/08 37/08 43/00 112 43/00 112 C07C 233/52 C07C 233/52 233/84 233/84 271/24 271/24 C07D 521/00 C07D 521/00 (72)発明者 岸野 淳二 兵庫県神戸市須磨区神の谷3丁目3番17 号 (72)発明者 本摩 恒利 奈良県生駒市青山台117−42 (56)参考文献 特開 平2−180862(JP,A) 特開 昭63−139161(JP,A) 特開 昭61−49(JP,A) 特開 昭64−52751(JP,A) 特開 平2−218660(JP,A) 特開 平4−211642(JP,A) (58)調査した分野(Int.Cl.7,DB名) A61K 31/201 A61K 31/231 A61K 31/335 A61K 31/341 A61K 31/343 A61K 31/352 A61K 31/357 A61K 31/36 A61K 31/38 A61K 31/381 A61K 31/403 A61K 31/404 A61K 31/41 A61K 31/4164 A61K 31/42 A61K 31/423 A61K 31/4245 A61K 31/426 A61K 31/433 A61K 31/4402 A61K 31/4406 A61K 31/4409 A61K 31/473 A61K 31/5375 A61K 31/5415 A61K 31/63 A61K 31/655 A61K 31/66 A61P 11/02 A61P 11/06 A61P 27/16 A61P 29/00 A61P 37/08 A61P 43/00 C07C 233/52 C07C 233/84 C07C 271/24 C07D 521/00 CA(STN) EMBASE(STN) MEDLINE(STN)
Claims (15)
- 【請求項1】式(I): を表わし、 Aはヘテロ原子もしくはフェニレンを介在していてもよ
く、オキソ基を有していてもよく、および/または不飽
和結合を有していてもよいアルキレン; Bは水素、アルキル、アラルキルまたはアシル; RはCOOR1、CH2OR2またはCON(R3)R4; R1は水素またはアルキル; R2は水素またはアルキル; R3およびR4はそれぞれ独立して水素、アルキル、ヒドロ
キシまたはアルキルスルホニル; X1は単結合、フェニレン、ナフチレン、チオフェンジイ
ル、インドールジイルまたはオキサゾールジイル; X2は単結合、−N=N−、−N=CH−、−CH=N−、−
CH=N−N−、−CH=N−O−、−C=NNHCSNH−、−
C=NNHCONH−、−CH=CH−、−CH(OH)−、−C(C
l)=C(Cl)−、−(CH2)n−、エチニレン、−N
(R5)−、−N(R51)CO−、−N(R52)SO2−、−N
(R53)CON(R54)−、−CON(R55)−、−SO2N(R56)
−、−O−、−S−、−SO−、−SO2−、−CO−、オキ
サジアゾールジイル、チアジアゾールジイルまたはテト
ラゾールジイル; X3はアルキル、アルケニル、アルキニル、アリール、ア
ラルキル、ヘテロ環、シクロアルキル、シクロアルケニ
ル、チアゾリニリデンメチル、チアゾリジニリデンメチ
ル、−CH=NR6または−N=C(R7)R8; R5、R51、R52、R53、R54、R55およびR56は水素またはア
ルキル; R6は水素、アルキル、ヒドロキシ、アルコキシ、カルバ
モイルオキシ、チオカルバモイルオキシ、ウレイドまた
はチオウレイド; R7およびR8はそれぞれ独立してアルキル、アルコキシま
たはアリール; nは1または2; Zは_−CO−; mは0または1; これらの定義において、置換基が環状のものはニトロ、
アルコキシ、スルファモイル、置換もしくは非置換アミ
ノ、アシル、アシルオキシ、ヒドロキシ、ハロゲン、ア
ルキル、アルキニル、カルボキシ、アルコキシカルボニ
ル、アラルコキシカルボニル、アリールオキシカルボニ
ル、メシルオキシ、シアノ、アルケニルオキシ、ヒドロ
キシアルキル、トリフルオロメチル、アルキルチオ、−
N=PPh3、オキソ、チオキソ、ヒドロキシイミノ、アル
コキシイミノ、フェニルおよびアルキレンジオキシから
選ばれる1〜3個の基で置換されていてもよい) である化合物もしくはその塩またはそれらの水和物を有
効成分として含有するPGD2拮抗剤。 - 【請求項2】有効成分が式(I)で示される化合物にお
いて、 を表し、mが0である化合物もしくはその塩またはそれ
らの水和物である請求の範囲第1項記載のPGD2拮抗剤。 - 【請求項3】有効成分が式(I)で示される化合物にお
いて、 を表わし、mが1のとき、X1およびX2がともに単結合で
あり、X3がハロゲンで置換されていてもよいフェニルで
ある化合物もしくはその塩またはそれらの水和物である
請求の範囲第1項記載のPGD2拮抗剤。 - 【請求項4】有効成分が式(I)で示される化合物にお
いて、 を表わし、mが1のとき、X1がフェニレン、X2が−CH2
−または−N=N−であり、X3がフェニルである化合物
もしくはその塩またはそれらの水和物である請求の範囲
第1項記載のPGD2拮抗剤。 - 【請求項5】鼻閉治療剤である請求の範囲第1項記載の
PGD2拮抗剤。 - 【請求項6】式(I b): を表わし、 Aはヘテロ原子もしくはフェニレンを介在していてもよ
く、オキソ基を有していてもよく、および/または不飽
和結合を有していてもよいアルキレン; Bは水素、アルキル、アラルキルまたはアシル; RはCOOR1、CH2OR2またはCON(R3)R4; R1は水素またはアルキル; R2は水素またはアルキル; R3およびR4はそれぞれ独立して水素、アルキル、ヒドロ
キシまたはアルキルスルホニル; X1は単結合、フェニレン、ナフチレン、チオフェンジイ
ル、インドールジイルまたはオキサゾールジイル; X2は単結合、−N=N−、−N=CH−、−CH=N−、−
CH=N−N−、−CH=N−O−、−C=NNHCSNH−、−
C=NNHCONH−、−CH=CH−、−CH(OH)−、−C(C
l)=C(Cl)−、−(CH2)n−、エチニレン、−N
(R5)−、−N(R51)CO−、−N(R52)SO2−、−N
(R53)CON(R54)−、−CON(R55)−、−SO2N(R56)
−、−O−、−S−、−SO−、−SO2−、−CO−、オキ
サジアゾールジイル、チアジアゾールジイルまたはテト
ラゾールジイル; X3はアルキル、アルケニル、アルキニル、アリール、ア
ラルキル、ヘテロ環、シクロアルキル、シクロアルケニ
ル、チアゾリニリデンメチル、チアゾリジニリデンメチ
ル、−CH=NR6−または−N=C(R7)R8; R5、R51、R52、R53、R54、R55およびR56は水素またはア
ルキル; R6は水素、アルキル、ヒドロキシ、アルコキシ、カルバ
モイルオキシ、チオカルバモイルオキシ、ウレイドまた
はチオウレイド; R7およびR8はそれぞれ独立してアルキル、アルコキシま
たはアリール; nは1または2; これらの定義において、置換基が環状のものはニトロ、
アルコキシ、スルファモイル、置換もしくは非置換アミ
ノ、アシル、アシルオキシ、ヒドロキシ、ハロゲン、ア
ルキル、アルキニル、カルボキシ、アルコキシカルボニ
ル、アラルコキシカルボニル、アリールオキシカルボニ
ル、メシルオキシ、シアノ、アルケニルオキシ、ヒドロ
キシアルキル、トリフルオロメチル、アルキルチオ、−
N=PPh3、オキソ、チオキソ、ヒドロキシイミノ、アル
コキシイミノ、フェニルおよびアルキレンジオキシから
選ばれる1〜3個の基で置換されていてもよい。 ただし、X1およびX2が単結合であり、X3が非置換フェニ
ルである場合およびX1が単結合でX2が−O−であると
き、X3がベンジルである場合を除く) で示される化合物もしくはその塩またはそれらの水和
物。 - 【請求項7】式(I b)で示される化合物において、 である請求の範囲第6項記載の化合物もしくはその塩ま
たはそれらの水和物。 - 【請求項8】RがCOOR1である請求の範囲第7項記載の
化合物もしくはその塩またはそれらの水和物。 - 【請求項9】X1がフェニレンまたはチオフェンジイル、
X2が単結合、−N=N−、−CH=CH−、エチニレン、−
O−、−S−、−CO−、−CON(R55)−または−N(R
51)CO−およびX3がフェニルまたはチエニルである請求
の範囲第7項記載の化合物もしくはその塩またはそれら
の水和物。 - 【請求項10】式(I b)で示される化合物において、 である請求の範囲第6項記載の化合物もしくはその塩ま
たはそれらの水和物。 - 【請求項11】Bが水素、X1およびX2がともに単結合で
あり、X3がチエニル、チアゾリル、チアジアゾリル、イ
ソチアゾリル、ピロリル、ピリジル、ベンゾフリル、ベ
ンゾイミダゾリル、ベンゾチエニル、ジベンゾフリル、
ジベンゾチエニル、キノリルまたはインドリルである請
求の範囲第10項記載の化合物もしくはその塩またはそれ
らの水和物。 - 【請求項12】X1がフェニレン、チオフェンジイル、イ
ンドールジイルまたはオキサゾールジイル、X2が単結
合、−N=N−、−CH=CH−、エチニレン、−S−また
は−O−、およびX3がアリールまたはヘテロ環である請
求の範囲第10項記載の化合物もしくはその塩またはそれ
らの水和物。 - 【請求項13】式(I b)で示される化合物において、 を表わし、Aはオキソ基または不飽和結合を有していて
もよいアルキレン、Bは水素、RはCOOHまたはCH2OH、X
1およびX2は単結合、X3は置換または非置換のベンゾチ
エニルである請求の範囲第6項記載の化合物もしくはそ
の塩またはそれらの水和物。 - 【請求項14】請求の範囲第6項〜第13項のいずれかに
記載の化合物若しくはその塩またはそれらの水和物を有
効成分として含有するPGD2拮抗剤。 - 【請求項15】鼻閉治療剤である請求の範囲第14項記載
のPGD2拮抗剤。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP15457595 | 1995-06-21 | ||
JP7-154575 | 1995-06-21 |
Related Child Applications (1)
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---|---|---|---|
JP2001073708A Division JP3701878B2 (ja) | 1995-06-21 | 2001-03-15 | ビシクロ環系アミノ誘導体およびそれを含有するpgd2拮抗剤 |
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JP3195361B2 true JP3195361B2 (ja) | 2001-08-06 |
Family
ID=15587229
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Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP50372497A Expired - Fee Related JP3195361B2 (ja) | 1995-06-21 | 1996-06-19 | ビシクロ環系アミノ誘導体およびそれを含有するpgd2拮抗剤 |
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EP (1) | EP0837052B1 (ja) |
JP (1) | JP3195361B2 (ja) |
KR (1) | KR100428601B1 (ja) |
CN (1) | CN1134411C (ja) |
AT (1) | ATE337294T1 (ja) |
AU (1) | AU714312B2 (ja) |
BR (1) | BR9608498B1 (ja) |
CA (1) | CA2225250C (ja) |
CZ (1) | CZ285870B6 (ja) |
DE (1) | DE69636478T2 (ja) |
DK (1) | DK0837052T3 (ja) |
EA (1) | EA000987B1 (ja) |
ES (1) | ES2270438T3 (ja) |
HU (1) | HUP9802678A3 (ja) |
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IL263996B2 (en) | 2016-07-07 | 2024-03-01 | Ironwood Pharmaceuticals Inc | Solid configurations of the SGC promoter |
CN114736240A (zh) | 2016-07-07 | 2022-07-12 | 赛克里翁治疗有限公司 | sGC刺激剂的磷前药 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
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DE3280020D1 (en) | 1981-12-23 | 1989-12-21 | Nat Res Dev | Prostaglandins |
US4837234A (en) | 1981-12-23 | 1989-06-06 | National Research Development Corporation | Prostaglandins |
US4526901A (en) * | 1984-01-26 | 1985-07-02 | E. R. Squibb & Sons, Inc. | 7-Oxabicycloheptane substituted oxamide prostaglandin analogs and their use in treating thrombolytic disease |
JPS6149A (ja) | 1984-06-12 | 1986-01-06 | Ono Pharmaceut Co Ltd | 新規な13―アザ―14―オキソ―TxA2類似化合物およびそれらを有効成分として含有するトロンボキサン起因疾患治療剤 |
CA1278577C (en) * | 1985-11-18 | 1991-01-02 | Tatsuo Tsuri | Bicyclic sulfonamide derivatives |
CA1294974C (en) | 1987-05-08 | 1992-01-28 | Sanji Hagishita | Bicyclic sulfonamide derivatives and process therefor |
EP0312906A3 (en) * | 1987-10-23 | 1990-09-05 | Ono Pharmaceutical Co., Ltd. | Novel sulfonamide derivatives |
JP2565746B2 (ja) * | 1987-10-23 | 1996-12-18 | 小野薬品工業株式会社 | 新規な炭素環系スルホンアミド誘導体 |
JPH0262546A (ja) | 1988-08-30 | 1990-03-02 | Asahi Chem Ind Co Ltd | 改良された光学用感光性樹脂組成物 |
CA2113787A1 (en) * | 1993-01-29 | 1994-07-30 | Nobuyuki Hamanaka | Carbocyclic sulfonamides |
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1996
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- 1996-06-19 ES ES96918841T patent/ES2270438T3/es not_active Expired - Lifetime
- 1996-06-19 CN CNB961963263A patent/CN1134411C/zh not_active Expired - Fee Related
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- 1996-06-19 HU HU9802678A patent/HUP9802678A3/hu unknown
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- 1996-06-19 KR KR1019970709573A patent/KR100428601B1/ko not_active IP Right Cessation
- 1996-06-19 EP EP96918841A patent/EP0837052B1/en not_active Expired - Lifetime
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2000
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