JP5005338B2 - フレグランスとして有用なカルバメート類 - Google Patents
フレグランスとして有用なカルバメート類 Download PDFInfo
- Publication number
- JP5005338B2 JP5005338B2 JP2006504173A JP2006504173A JP5005338B2 JP 5005338 B2 JP5005338 B2 JP 5005338B2 JP 2006504173 A JP2006504173 A JP 2006504173A JP 2006504173 A JP2006504173 A JP 2006504173A JP 5005338 B2 JP5005338 B2 JP 5005338B2
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- formula
- alkenyl
- optionally substituted
- compounds
- 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 - Lifetime
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- 239000003205 fragrance Substances 0.000 title claims abstract description 28
- 150000004657 carbamic acid derivatives Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 34
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 16
- -1 vinylic carbamates Chemical class 0.000 abstract description 25
- 238000000034 method Methods 0.000 abstract description 8
- 239000004615 ingredient Substances 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 description 30
- 125000003342 alkenyl group Chemical group 0.000 description 27
- 125000003545 alkoxy group Chemical group 0.000 description 19
- 239000000047 product Substances 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000000753 cycloalkyl group Chemical group 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 229920002554 vinyl polymer Polymers 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 235000019645 odor Nutrition 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- 125000003884 phenylalkyl group Chemical group 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000001326 naphthylalkyl group Chemical group 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- PLSMHHUFDLYURK-UHFFFAOYSA-N 2,3,4-trimethyl-3-pentanol Chemical compound CC(C)C(C)(O)C(C)C PLSMHHUFDLYURK-UHFFFAOYSA-N 0.000 description 2
- BKMMTJMQCTUHRP-UHFFFAOYSA-N 2-aminopropan-1-ol Chemical compound CC(N)CO BKMMTJMQCTUHRP-UHFFFAOYSA-N 0.000 description 2
- RTGLJCSUKOLTEM-UHFFFAOYSA-N 2-ethylhexyl carbonochloridate Chemical compound CCCCC(CC)COC(Cl)=O RTGLJCSUKOLTEM-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 2
- VAJFEOKPKHIPEN-UHFFFAOYSA-N 4-methyl-1,3-oxazolidin-2-one Chemical compound CC1COC(=O)N1 VAJFEOKPKHIPEN-UHFFFAOYSA-N 0.000 description 2
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 150000001793 charged compounds Chemical class 0.000 description 2
- HQKQRXZEXPXXIG-VJOHVRBBSA-N chembl2333940 Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@H]1[C@@](OC(C)=O)(C)CC2 HQKQRXZEXPXXIG-VJOHVRBBSA-N 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- RXRRUZYOMGDHLZ-UHFFFAOYSA-N hex-3-enyl carbonochloridate Chemical compound CCC=CCCOC(Cl)=O RXRRUZYOMGDHLZ-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- 150000002678 macrocyclic compounds Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- CZCBTSFUTPZVKJ-UHFFFAOYSA-N rose oxide Chemical compound CC1CCOC(C=C(C)C)C1 CZCBTSFUTPZVKJ-UHFFFAOYSA-N 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000341 volatile oil Substances 0.000 description 2
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 2
- AVJMJMPVWWWELJ-DHZHZOJOSA-N (2e)-1-methoxy-3,7-dimethylocta-2,6-diene Chemical compound COC\C=C(/C)CCC=C(C)C AVJMJMPVWWWELJ-DHZHZOJOSA-N 0.000 description 1
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 1
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- NVIPUOMWGQAOIT-UHFFFAOYSA-N (E)-7-Hexadecen-16-olide Natural products O=C1CCCCCC=CCCCCCCCCO1 NVIPUOMWGQAOIT-UHFFFAOYSA-N 0.000 description 1
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 1
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 1
- RNLHVODSMDJCBR-VURMDHGXSA-N (z)-3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-4-en-2-ol Chemical compound CC(O)C(C)\C=C/C1CC=C(C)C1(C)C RNLHVODSMDJCBR-VURMDHGXSA-N 0.000 description 1
- VPKMGDRERYMTJX-CMDGGOBGSA-N 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one Chemical compound CCC(=O)\C=C\C1C(C)=CCCC1(C)C VPKMGDRERYMTJX-CMDGGOBGSA-N 0.000 description 1
- BLXSFCHWMBESKV-UHFFFAOYSA-N 1-iodopentane Chemical compound CCCCCI BLXSFCHWMBESKV-UHFFFAOYSA-N 0.000 description 1
- AQTYZMUVWUNRIV-UHFFFAOYSA-N 2,3,4-trimethylpentan-3-yl n,n-dimethylcarbamate Chemical compound CC(C)C(C)(C(C)C)OC(=O)N(C)C AQTYZMUVWUNRIV-UHFFFAOYSA-N 0.000 description 1
- HMKKIXGYKWDQSV-SDNWHVSQSA-N 2-Pentyl-3-phenyl-2-propenal Chemical compound CCCCC\C(C=O)=C/C1=CC=CC=C1 HMKKIXGYKWDQSV-SDNWHVSQSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- NVKLJCMSDRFRIK-UHFFFAOYSA-N 2-ethylhexyl n-methyl-n-propan-2-ylcarbamate Chemical compound CCCCC(CC)COC(=O)N(C)C(C)C NVKLJCMSDRFRIK-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- YIGYAWHTWIGTAQ-UHFFFAOYSA-N 3,7-dimethylocta-1,6-dien-3-yl n,n-dimethylcarbamate Chemical compound CN(C)C(=O)OC(C)(C=C)CCC=C(C)C YIGYAWHTWIGTAQ-UHFFFAOYSA-N 0.000 description 1
- NGYMOTOXXHCHOC-UHFFFAOYSA-N 3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-2-ol Chemical compound CC(O)C(C)CCC1CC=C(C)C1(C)C NGYMOTOXXHCHOC-UHFFFAOYSA-N 0.000 description 1
- BKMQCRXFQNUSTR-UHFFFAOYSA-N 4-methyl-3-pentyl-1,3-oxazolidin-2-one Chemical compound CCCCCN1C(C)COC1=O BKMQCRXFQNUSTR-UHFFFAOYSA-N 0.000 description 1
- HBRXQSHUXIJOKV-UHFFFAOYSA-N 5-methyl-1,3-oxazolidin-2-one Chemical compound CC1CNC(=O)O1 HBRXQSHUXIJOKV-UHFFFAOYSA-N 0.000 description 1
- AUBLFWWZTFFBNU-UHFFFAOYSA-N 6-butan-2-ylquinoline Chemical compound N1=CC=CC2=CC(C(C)CC)=CC=C21 AUBLFWWZTFFBNU-UHFFFAOYSA-N 0.000 description 1
- NVIPUOMWGQAOIT-DUXPYHPUSA-N 7-hexadecen-1,16-olide Chemical compound O=C1CCCCC\C=C\CCCCCCCCO1 NVIPUOMWGQAOIT-DUXPYHPUSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 240000007087 Apium graveolens Species 0.000 description 1
- 235000015849 Apium graveolens Dulce Group Nutrition 0.000 description 1
- 235000010591 Appio Nutrition 0.000 description 1
- 240000007436 Cananga odorata Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- XRHCAGNSDHCHFJ-UHFFFAOYSA-N Ethylene brassylate Chemical compound O=C1CCCCCCCCCCCC(=O)OCCO1 XRHCAGNSDHCHFJ-UHFFFAOYSA-N 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- 235000018958 Gardenia augusta Nutrition 0.000 description 1
- 239000005792 Geraniol Substances 0.000 description 1
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 1
- 244000303040 Glycyrrhiza glabra Species 0.000 description 1
- 235000006200 Glycyrrhiza glabra Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 235000010254 Jasminum officinale Nutrition 0.000 description 1
- 240000005385 Jasminum sambac Species 0.000 description 1
- HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000004419 alkynylene group Chemical group 0.000 description 1
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
- YPZUZOLGGMJZJO-UHFFFAOYSA-N ambrofix Natural products C1CC2C(C)(C)CCCC2(C)C2C1(C)OCC2 YPZUZOLGGMJZJO-UHFFFAOYSA-N 0.000 description 1
- YPZUZOLGGMJZJO-LQKXBSAESA-N ambroxan Chemical compound CC([C@@H]1CC2)(C)CCC[C@]1(C)[C@@H]1[C@]2(C)OCC1 YPZUZOLGGMJZJO-LQKXBSAESA-N 0.000 description 1
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 235000000484 citronellol Nutrition 0.000 description 1
- 229940126208 compound 22 Drugs 0.000 description 1
- 229940125961 compound 24 Drugs 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000005610 enamide group Chemical group 0.000 description 1
- 229940093468 ethylene brassylate Drugs 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000002979 fabric softener Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- IFYYFLINQYPWGJ-VIFPVBQESA-N gamma-Decalactone Natural products CCCCCC[C@H]1CCC(=O)O1 IFYYFLINQYPWGJ-VIFPVBQESA-N 0.000 description 1
- PHXATPHONSXBIL-JTQLQIEISA-N gamma-Undecalactone Natural products CCCCCCC[C@H]1CCC(=O)O1 PHXATPHONSXBIL-JTQLQIEISA-N 0.000 description 1
- 229940020436 gamma-undecalactone Drugs 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- 239000010648 geranium oil Substances 0.000 description 1
- 235000019717 geranium oil Nutrition 0.000 description 1
- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 description 1
- JQZGNTSKGNLFBO-UHFFFAOYSA-N hex-3-enyl n,n-diethylcarbamate Chemical compound CCC=CCCOC(=O)N(CC)CC JQZGNTSKGNLFBO-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 229930007744 linalool Natural products 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000011477 liquorice Nutrition 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 229940043353 maltol Drugs 0.000 description 1
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000002088 nanocapsule Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 239000001738 pogostemon cablin oil Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000010666 rose oil Substances 0.000 description 1
- 235000019719 rose oil Nutrition 0.000 description 1
- 229930007790 rose oxide Natural products 0.000 description 1
- 239000010671 sandalwood oil Substances 0.000 description 1
- 239000001290 saussurea lappa clarke root oil Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- LVLANIHJQRZTPY-UHFFFAOYSA-N vinyl carbamate Chemical class NC(=O)OC=C LVLANIHJQRZTPY-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/46—8-Azabicyclo [3.2.1] octane; Derivatives thereof, e.g. atropine, ***e
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
- C07C271/42—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/44—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/22—Oxygen atoms attached in position 2 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring carbon atoms
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- C11B9/0007—Aliphatic compounds
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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Description
で表される非ビニルカルバミン酸エステルのフレグランス成分としての使用は、過去の文献に記載されていない。
すなわち、本発明は、第1の観点において、非ビニル第3級カルバメート類、すなわちN−ビニルまたはO−ビニル置換基を有さない、分子量が350未満の、好ましくは分子量が300以下の第3級カルバメートのフレグランス成分としての使用に関する。
R1およびR2は、
(a)C1〜C11アルキル、好ましくはC1〜C6アルキル、例えばメチル、エチル、プロピル、イソプロピル;C3〜C11アルク−(>1)−エニル、好ましくはC3〜C6アルケニル、例えばプロプ−2−エニル;またはC2〜C11アルキニル基;および
(b)アルキル、アルケニルおよびアルコキシ基(1個または2個以上)で随意に置換されたシクロアルキル;アルキル、アルケニルおよびアルコキシ基(1個または2個以上)で随意に置換されたC3〜C8シクロアルケニル;または芳香環がアルキル、アルケニルおよびアルコキシ基(1個または2個以上)で随意に置換されたフェニルもしくはナフチル;および
からなる群から独立に選択され、
Rは、
(a)C1〜C11アルキル;C3〜C11アルク−(>1)−エニル;またはC2〜C11アルキ二ル基;および
(b)アルキル、アルケニルおよびアルコキシ基(1個または2個以上)で随意に置換されたシクロアルキル;アルキル、アルケニルおよびアルコキシ基(1個または2個以上)で随意に置換されたC3〜C8シクロアルケニル;またはアルキル、アルケニルおよびアルコキシ基(1個または2個以上)で随意に置換されたフェニルもしくはナフチル;および
(c)シクロアルキル環がアルキル、アルケニルおよびアルコキシ基(1個または2個以上)で随意に置換されたC4〜C14シクロアルキルアルキル;シクロアルケニル環がアルキル、アルケニルおよびアルコキシ基(1個または2個以上)で随意に置換されたC4〜C14シクロアルケニルアルキル;または芳香環がアルキル、アルケニルおよびアルコキシ基(1個または2個以上)で随意に置換されたフェニルアルキルもしくはナフチルアルキル;および
(e)芳香族複素環、例えばピリジル、フリル;アリールアルキル複素環、例えばフリルメチル、ピリジルメチル、ピリジルエチル;複素環、例えばジヒドロフリル、テトラヒドロフリル;または、シクロアルキル複素環、例えば、ジヒドロフリルメチル、テトラヒドロフリルメチル;であって、環がアルキル、アルケニルおよびアルコキシ基(1個または2個以上)によって随意に置換され、環が5〜6員を有し、ヘテロ原子が酸素または窒素であるもの;
からなる群から選択され、
R、R1およびR2は合わせて7〜18個の炭素原子、より好ましくは7〜16個の炭素原子、最も好ましくは8〜12個の炭素原子を有するか、または
(a)C1〜C6アルキル;C3〜C5アルク−(>1)−エニル;またはC2〜C5アルキニル基;および
(b)アルキルおよびアルケニル基(1個または2個以上)によって随意に置換されたC3〜C6シクロアルキル;アルキルおよびアルケニル基(1個または2個以上)で随意に置換されたC3〜C6シクロアルケニル;またはアルキルおよびアルケニル基(1個または2個以上)で随意に置換されたフェニル;および
(c)シクロアルキル環がアルキルおよびアルケニル基(1個または2個以上)で随意に置換されたC4〜C8シクロアルキルアルキル;または芳香環がアルキルおよびアルケニル基(1個または2個以上)で随意に置換されたフェニルアルキル;
からなる群から選択され、
RおよびR2は結合先の原子と一緒に、アルキルおよびアルケニル基(1個または2個以上)で随意に置換された5〜8員複素環を形成し;R、R1およびR2は合わせて7〜18個の炭素原子、より好ましくは7〜16個の炭素原子、最も好ましくは8〜12個の炭素原子を有する。
好ましいのは式(I)による化合物であって、式中R1およびR2は合わせて2〜13個の炭素原子、より好ましくは2〜9個の炭素原子、最も好ましくは2〜6個の炭素原子を有するものである。R1=R2である、本発明による化合物も好ましい。
式(I)の化合物の中には、文献に記載されているものもあるが、その他は記載されておらず、新規である。
・精油およびエキス、例えば、海狸香、カスタスルート油(costus root oil)、オークモスアブソリュート(oak moss absolute)、ゼラニウム油、ジャスミンアブソリュート(jasmin absolute)、パッチュウリ油(patchouli oil)、バラ油(rose oil)、ビャクダン油(sandalwood oil)、またはイランイラン香油(ylang-ylang oil);
・アルコール類、例えば、シトロネロール、Ebanol(登録商標)、オイゲノール、ゲラニオール、Super Muguet(登録商標)、リナロール、フェニルエチルアルコール、Sandalore(登録商標)、テルピネオール、またはTimberol(登録商標);
・アルデヒド類およびケトン類、例えば、α−アミルシンナムアルデヒド、Georygywood(登録商標)、ヒドロキシシトロネラール、Iso E Super(登録商標)、Isoraldeine(登録商標)、Hedione(登録商標)、マルトール、メチルセドリルケトン、メチルイオノンまたはバニリン;
・エーテルおよびアセタール類、例えば、Ambrox(登録商標)、ゲラニルメチルエーテル、ローズオキシド(rose oxide)またはSpirambrene(登録商標);
・エステル類およびラクトン類、例えば、ベンジルアセテート、セドリルアセテート、γ−デカラクトン、Helvetolide(登録商標)、γ−ウンデカラクトンまたはベチベニルアセテート(vetivenyl acetate);
・大環状分子、例えば、アンブレットリド(ambrettolide)、エチレンブラシレート(ethylene brassylate)またはExaltolide(登録商標);
・複素環分子、例えば、イソブチルキノリン。
したがって、本発明はさらに、分子量350未満の第3級カルバメートをフレグランス成分として組み込むことを含む、フレグランス製品の製造方法を提供する。
(a)式(VI)の第1級アミンを、塩基、例えばNaHの存在下で、式(IV)のクロロギ酸アルキルエステルと反応させて式(V)の第2級カルバメートを得る工程、およびその後の
(b)前記式(V)の第2級カルバメートを、塩基、例えばNaHの存在下で、式:
R2−X
式中、XはBr−、Cl−、J−、またはR4−SO4 −であり、R4はメチルまたはトリルである、
で表されるアルキル化剤と反応させる工程
による、式(I)の化合物の製造方法であって、
R、R1およびR2は上記に定義されるとおりであるとともに、工程(a)および(b)は、同一の反応容器において逐次的に行われる方法である。
次に、以下の非限定的な例を参照して、本発明をさらに説明する。
ジエチルアミン(9.1g、125mmol、1.25当量)を、2%NaOH水溶液(200ml)に添加し、その結果得られる混合物を0℃まで冷却した(氷浴)。この温度で、ジエチルエーテル(200ml)中のクロロギ酸ヘキス−3−エニルエステル(16.2g、100mmol)を35分間にわたって添加した。添加完了後に、冷却浴を取り除き、1.5時間にわたり攪拌を続けた。混合物を、2N HCl水溶液で酸性化し、相を分離し、有機相を塩水で洗い、MgSO4上で乾燥させた。粗生成物を分割蒸留(74〜76℃/0.05mbar)によって精製して、18.2g(92%)の生成物を得た。
トルエン(50ml)中の2,3,4−トリメチル−ペンタン−3−オール(13.0g、100mmol、1当量)の溶液を、トルエン(50ml)中のNaH懸濁液(鉱油中で55%、4.80g、110mmol、1.1当量)に加えた。この混合物を、100℃まで1時間加熱して、次いで0℃まで冷却した。トルエン(30ml)中のジメチルカルバモイルクロリド(12.9g、120mmol、1.2当量)の溶液を、45分間にわたって添加した。その結果として得られる懸濁液を、室温で19時間攪拌し、次いで、MTBEで希釈して実施例1に示すようにワークアップした。粗生成物を0.05mbar/52〜61℃で蒸留することによって、61%の生成物が得られた。
イソプロピルアミンの溶液(2.95g、50mmol、1当量)を、室温でTHF(25ml)中のNaHの懸濁液(鉱油中で55%、2.40g、55mmol、1.1当量)に加えた。混合物を、18時間、40℃まで昇温し、次いでTHF(25ml)中のクロロギ酸2−エチル−ヘキシルエステルを、30分間にわたって滴加した。さらに4時間の攪拌の後に、THF(25ml)中のNaHの懸濁液(鉱油中で55%、2.40g、55mmol、1.1当量)を加え、続いてTHF(20ml)中の硫酸ジメチルの溶液(5.2ml、55mmol、1.1当量)を加えた。この混合物を70℃まで16時間加熱し、次いで、水(50ml)を加えて加水分解した。この加水分解混合物を、過剰な硫酸ジメチルを破壊するために、さらに70℃まで1.5時間加熱して、次いでMTBEで希釈して実施例1に記載するようにワークアップした。この粗生成物を、0.06mbar/94〜95℃で蒸留して8.8g(77%)の生成物を得た。
4.1.4−メチル−オキサゾリジン−2−オン(K. Rein et al., J. Am. Chem. Soc. 1989, 111, 2211.参照)
炭酸ジエチル(46.8g、397mmol、1.2当量)を、触媒量(1mol%)の新しく調製したNaOEt(76mgのNaおよび0.4mlのEtOHからのもの)に添加した。次いで、2−アミノプロパノール(24.6g、328mmol、1当量)を添加し、その結果として得られた溶液を125℃に加熱し、その時点でEtOHの留出が始まった。5時間後に、混合物を室温まで冷却して、過剰の炭酸ジエチルを高真空0.5mbar/50℃で除去して、分析的に純粋な5−メチルオキサゾリジノン33.0g(99%)を淡黄色の油として得た。
THF(100ml)中の4−メチル−オキサゾリジン−2−オン(18.0g、178mmol)を、滴下ロートを介してゆっくりとTHF(400ml)中のヘキサン洗浄NaH(鉱油中で60%、7.12g、178mmol、1.0当量)のスラリーに加え、そのときにH2発生が観察された。純ヨードペンタン(70.51g、356mmol、2.0当量)を迅速に加えて、混合物を室温で1時間攪拌し、次いで加熱して60時間還流させた。5℃まで冷却した後に、2N H2SO4(180ml)をゆっくりと添加した。この混合物をMTBEで抽出して、通常どおりワークアップした。Widmerカラム(Widmer-column)上において115℃/0.08mbarで蒸留することによって、生成物を、わずかに黄色がかった液体(20.54g、73%)として得た。
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ES (1) | ES2338422T3 (ja) |
MX (1) | MXPA05010888A (ja) |
WO (1) | WO2004089880A2 (ja) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2010122178A2 (en) * | 2010-05-25 | 2010-10-28 | Symrise Gmbh & Co. Kg | Cyclohexyl carbamate compounds as skin and/or hair lightening actives |
EP2389922A1 (en) | 2010-05-25 | 2011-11-30 | Symrise AG | Cyclohexyl carbamate compounds as anti-ageing actives |
WO2010097479A2 (en) * | 2010-05-25 | 2010-09-02 | Symrise Gmbh & Co. Kg | Cyclohexyl carbamate compounds as active anti-cellulite ingredients |
Family Cites Families (24)
Publication number | Priority date | Publication date | Assignee | Title |
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DE296889C (ja) * | ||||
US1252452A (en) * | 1917-11-23 | 1918-01-08 | Synthetic Patents Co Inc | Pharmaceutical product. |
US2060733A (en) * | 1934-09-04 | 1936-11-10 | Du Pont | Process of treating cellulose and derivatives thereof |
US2197479A (en) * | 1936-01-04 | 1940-04-16 | Du Pont | Carbamic acid esters of monoalkyl ethers of polyalkylene glycols |
US2460291A (en) * | 1944-09-02 | 1949-02-01 | Du Pont | Process for preparation of terpene alcohols |
US2517965A (en) * | 1948-03-23 | 1950-08-08 | Pittsburgh Plate Glass Co | Purification of carbonic acid esters |
DE960896C (de) * | 1953-07-25 | 1957-03-28 | Cassella Farbwerke Mainkur Ag | Verfahren zur Herstellung von Tetrahydrofurfurylalkoholcarbaminsaeureestern |
DE1171200B (de) * | 1961-05-06 | 1964-05-27 | Schering Ag | Insektizide synergistische Gemische |
DE1242590B (de) | 1964-02-14 | 1967-06-22 | Hoechst Ag | Verfahren zur Herstellung von N-Vinyl-carbaminsaeureestern |
GB1116005A (en) | 1966-02-21 | 1968-06-06 | Dow Chemical Co | Vinyl n-heterocyclic carbamates, process for their production and polymers thereof |
JPS5710085B2 (ja) * | 1973-05-04 | 1982-02-24 | ||
US4190591A (en) * | 1977-01-21 | 1980-02-26 | Givaudan Corporation | Odorant and flavorant |
DE2704904A1 (de) * | 1977-02-05 | 1978-08-10 | Henkel Kgaa | Kosmetische mittel mit einem gehalt an haut-feuchthaltemitteln |
US4772695A (en) | 1982-09-24 | 1988-09-20 | Societe Nationale Des Poudres Et Explosifs | Process for the preparation of vinyl carbamates |
DE3312498A1 (de) | 1983-04-07 | 1984-10-11 | Bayer Ag, 5090 Leverkusen | Carbamidsaeureester |
DE3801082A1 (de) * | 1987-04-28 | 1988-11-17 | Bayer Ag | Mittel zur insekten- und milbenabwehr |
US5472946A (en) * | 1988-04-08 | 1995-12-05 | Peck; James V. | Transdermal penetration enhancers |
FR2696471B1 (fr) * | 1992-10-02 | 1994-12-23 | Inst Textile De France | Utilisation de la vanilline et de ses dérivés comme agents de protection anti-UV. |
US6583106B2 (en) | 1997-01-24 | 2003-06-24 | Alzo International, Inc. | Monohydric alcohol derived urethanes and their use in cosmetic formulations |
EP0952142B1 (en) | 1998-04-20 | 2006-10-18 | Givaudan SA | Compounds with protected hydroxy groups |
AU3006800A (en) * | 1999-02-26 | 2000-09-14 | University Of South Florida | Efficient carbamate synthesis |
GB2360793A (en) * | 2000-03-29 | 2001-10-03 | Unilever Plc | Improving perfume deposition or retention on fabrics |
DE10028764A1 (de) | 2000-06-09 | 2001-12-20 | Henkel Kgaa | Urethane basierend auf organoleptisch aktiven Duftalkoholen |
GB0214342D0 (en) * | 2002-06-21 | 2002-07-31 | Givaudan Sa | Insect repellents |
-
2004
- 2004-04-14 ES ES04727204T patent/ES2338422T3/es not_active Expired - Lifetime
- 2004-04-14 WO PCT/CH2004/000227 patent/WO2004089880A2/en active Application Filing
- 2004-04-14 AT AT04727204T patent/ATE453616T1/de not_active IP Right Cessation
- 2004-04-14 JP JP2006504173A patent/JP5005338B2/ja not_active Expired - Lifetime
- 2004-04-14 EP EP04727204A patent/EP1613587B1/en not_active Expired - Lifetime
- 2004-04-14 US US10/552,655 patent/US8222200B2/en active Active
- 2004-04-14 MX MXPA05010888A patent/MXPA05010888A/es active IP Right Grant
- 2004-04-14 DE DE602004024876T patent/DE602004024876D1/de not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
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WO2004089880A2 (en) | 2004-10-21 |
WO2004089880A3 (en) | 2005-05-06 |
MXPA05010888A (es) | 2005-11-25 |
US8222200B2 (en) | 2012-07-17 |
EP1613587A2 (en) | 2006-01-11 |
DE602004024876D1 (de) | 2010-02-11 |
EP1613587B1 (en) | 2009-12-30 |
ES2338422T3 (es) | 2010-05-07 |
US20060270588A1 (en) | 2006-11-30 |
JP2006523244A (ja) | 2006-10-12 |
ATE453616T1 (de) | 2010-01-15 |
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