JPS6211000B2 - - Google Patents
Info
- Publication number
- JPS6211000B2 JPS6211000B2 JP50104464A JP10446475A JPS6211000B2 JP S6211000 B2 JPS6211000 B2 JP S6211000B2 JP 50104464 A JP50104464 A JP 50104464A JP 10446475 A JP10446475 A JP 10446475A JP S6211000 B2 JPS6211000 B2 JP S6211000B2
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- alkyl
- compound
- methyl
- estrene
- 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
Links
- 238000000034 method Methods 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 29
- -1 acyl hypoiodite Chemical compound 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 6
- GRXPVLPQNMUNNX-MHJRRCNVSA-N estrane Chemical compound C1CC2CCCC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 GRXPVLPQNMUNNX-MHJRRCNVSA-N 0.000 claims description 4
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 claims 1
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 claims 1
- 229960003399 estrone Drugs 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 24
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 13
- 229910052740 iodine Inorganic materials 0.000 description 13
- 239000011630 iodine Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 150000003431 steroids Chemical class 0.000 description 13
- 239000007858 starting material Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000005977 Ethylene Substances 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 125000004043 oxo group Chemical group O=* 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- WELNRNVZXWUOGT-QXUSFIETSA-N (8r,9s,10r,13s,14s)-13-methyl-1,2,4,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-dione Chemical compound C1C(=O)CC[C@@H]2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 WELNRNVZXWUOGT-QXUSFIETSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- ZMFAMKUTHVPEHP-VNIVASGNSA-N (8R,9S,10R,13S,14S)-3,17-dioxo-1,2,4,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-13-carbaldehyde Chemical compound C1C(=O)CC[C@@H]2[C@H]3CC[C@](C=O)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 ZMFAMKUTHVPEHP-VNIVASGNSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 description 4
- OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000007857 hydrazones Chemical class 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 4
- 150000007659 semicarbazones Chemical class 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- WWYNJERNGUHSAO-XUDSTZEESA-N (+)-Norgestrel Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](CC)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 WWYNJERNGUHSAO-XUDSTZEESA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 229960004400 levonorgestrel Drugs 0.000 description 3
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 3
- 238000013048 microbiological method Methods 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000000186 progesterone Substances 0.000 description 3
- 229960003387 progesterone Drugs 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
- 235000019345 sodium thiosulphate Nutrition 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- GFPSIMORZDATOE-PNKHAZJDSA-N (8R,9S,10R,13S,14S)-13-methyl-2,4,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one Chemical compound C1C=C2CC(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 GFPSIMORZDATOE-PNKHAZJDSA-N 0.000 description 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 2
- 241000122824 Aspergillus ochraceus Species 0.000 description 2
- LPLGAIGBKGBGNV-QXUSFIETSA-N C1CCC[C@@H]2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 Chemical compound C1CCC[C@@H]2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 LPLGAIGBKGBGNV-QXUSFIETSA-N 0.000 description 2
- RWNKSTSCBHKHTB-UHFFFAOYSA-N Hexachloro-1,3-butadiene Chemical compound ClC(Cl)=C(Cl)C(Cl)=C(Cl)Cl RWNKSTSCBHKHTB-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CIHXIRAAMAUYLZ-UHFFFAOYSA-N [K+].[K+].[C-]#[C-] Chemical compound [K+].[K+].[C-]#[C-] CIHXIRAAMAUYLZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000003180 beta-lactone group Chemical group 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003433 contraceptive agent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 229960004719 nandrolone Drugs 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- NDVLRABJIQAIOM-PNKHAZJDSA-N (8r,9s,10r,13s,14s)-13-methyl-1,2,3,4,7,8,9,10,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene Chemical compound C1C=C2CCCC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 NDVLRABJIQAIOM-PNKHAZJDSA-N 0.000 description 1
- OLYAEHZZXXLNQQ-QXUSFIETSA-N (8r,9s,10r,13s,14s)-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-one Chemical compound C1CC[C@@H]2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 OLYAEHZZXXLNQQ-QXUSFIETSA-N 0.000 description 1
- JFEPJTGMGDGPHJ-PNKHAZJDSA-N (8r,9s,10r,13s,14s)-13-methyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 JFEPJTGMGDGPHJ-PNKHAZJDSA-N 0.000 description 1
- QLNOWXZCDMQJRK-PUMWCKSCSA-N (8s,9s,10r,13s,14s)-13-methyl-2,6,7,8,9,10,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthrene-3,11,17-trione Chemical compound O=C1CC[C@@H]2[C@H]3C(=O)C[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 QLNOWXZCDMQJRK-PUMWCKSCSA-N 0.000 description 1
- JRIZOGLBRPZBLQ-QXUSFIETSA-N 19-Norandrostenedione Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 JRIZOGLBRPZBLQ-QXUSFIETSA-N 0.000 description 1
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 description 1
- PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000223211 Curvularia lunata Species 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 241000893212 Pestalotia Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 241000235546 Rhizopus stolonifer Species 0.000 description 1
- 241000989744 Royena Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 229960002478 aldosterone Drugs 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 230000003509 anti-fertility effect Effects 0.000 description 1
- 230000002513 anti-ovulatory effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229940124558 contraceptive agent Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002084 enol ethers Chemical class 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 150000002162 estranes Chemical class 0.000 description 1
- 230000001076 estrogenic effect Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical group C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- UGVPKMAWLOMPRS-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].CC[CH2-] UGVPKMAWLOMPRS-UHFFFAOYSA-M 0.000 description 1
- 150000002730 mercury Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- NPAGDVCDWIYMMC-IZPLOLCNSA-N nandrolone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 NPAGDVCDWIYMMC-IZPLOLCNSA-N 0.000 description 1
- 229940127234 oral contraceptive Drugs 0.000 description 1
- 239000003539 oral contraceptive agent Substances 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
- 230000000737 periodic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001072 progestational effect Effects 0.000 description 1
- 230000003623 progesteronic effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000006103 sulfonylation Effects 0.000 description 1
- 238000005694 sulfonylation reaction Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0051—Estrane derivatives
- C07J1/0081—Substituted in position 17 alfa and 17 beta
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/002—Carbocyclic rings fused
- C07J53/004—3 membered carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/001—Oxiranes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Description
ãçºæã®è©³çŽ°ãªèª¬æã
æ¬çºæã¯ã11βâããããã·â18âã¢ã«ãã«â
ãšã¹ãã©ã³ååç©ã®æ°èŠãªè£œé æ¹æ³åã³ãã®æ°èŠ
ãªäžéçæç©ã«ä¿ãã
ãšã¹ãã©ã³ååç©ã®æ°èŠãªè£œé æ¹æ³åã³ãã®æ°èŠ
ãªäžéçæç©ã«ä¿ãã
18âã¢ã«ãã«âãšã¹ãã©ã³ååç©ã¯è¬çåŠäžé
èŠãª19âãã«âã¹ããã€ãã§ããããã®ãããªå
åç©ã®ïŒäŸã¯ããã«ã²ã¹ãã¬ã«ïŒïŒ17αâãšãã
ã«â17βâããããã·â18âã¡ãã«ââ³ïŒâãšã¹
ãã¬ã³âïŒâãªã³ïŒã§ãããåŸå£ããã²ã¹ããã³
ïŒé»äœãã«ã¢ã³ïŒãšããŠé©çšãåŸãããšãç¥èŠã
ããŠãããç¹ã«é¿åŠè¬ã®ããã²ã¹ããã³æåãšã
ãŠäœ¿çšããããæç®ã«ã¯çš®ã ã®ãã«ã¢ã³æ§äœçšç¹
æ§ãæããå€ãã®18âã¢ã«ãã«âãšã¹ãã©ã³åå
ç©ãé瀺ãããŠããããããã®ååç©ã¯ãéåžžã
察å¿ãã13âã¡ãã«ååç©ããå¹åã匷ãã
èŠãª19âãã«âã¹ããã€ãã§ããããã®ãããªå
åç©ã®ïŒäŸã¯ããã«ã²ã¹ãã¬ã«ïŒïŒ17αâãšãã
ã«â17βâããããã·â18âã¡ãã«ââ³ïŒâãšã¹
ãã¬ã³âïŒâãªã³ïŒã§ãããåŸå£ããã²ã¹ããã³
ïŒé»äœãã«ã¢ã³ïŒãšããŠé©çšãåŸãããšãç¥èŠã
ããŠãããç¹ã«é¿åŠè¬ã®ããã²ã¹ããã³æåãšã
ãŠäœ¿çšããããæç®ã«ã¯çš®ã ã®ãã«ã¢ã³æ§äœçšç¹
æ§ãæããå€ãã®18âã¢ã«ãã«âãšã¹ãã©ã³åå
ç©ãé瀺ãããŠããããããã®ååç©ã¯ãéåžžã
察å¿ãã13âã¡ãã«ååç©ããå¹åã匷ãã
倩ç¶ã¹ããã€ããã«ã¢ã³ã¯ã13äœã«ã¡ãã«åºã
æãããã¢ã«ãã¹ããã³ã«æŒããããã«ãã®ã¡ã
ã«åºã¯äŸå€çã«çœ®æãããŠãããæ²»çã®ããã«é©
çšå¯èœãªå€ãã®åæ19âãã«âã¹ããã€ãã¯ã倩
ç¶ã¹ããã€ãããåºçºãã¹ããã€ãéªšæ Œäžã®çœ®æ
åºãå€æ§åã³ïŒåã¯é€å»ããã¹ããã€ãå ã«çœ®æ
åºãå°å ¥ãã䞊ã³ã«ïŒåã¯äºéçµåãå°å ¥ããã
ã¯é£œåãããæ¹æ³ã§ãç£æ¥çç£èŠæš¡ã§è£œé ãããŠ
ããããããã®åå¿äžã13âã¡ãã«åºã¯äžå€ã§ã
ãã
æãããã¢ã«ãã¹ããã³ã«æŒããããã«ãã®ã¡ã
ã«åºã¯äŸå€çã«çœ®æãããŠãããæ²»çã®ããã«é©
çšå¯èœãªå€ãã®åæ19âãã«âã¹ããã€ãã¯ã倩
ç¶ã¹ããã€ãããåºçºãã¹ããã€ãéªšæ Œäžã®çœ®æ
åºãå€æ§åã³ïŒåã¯é€å»ããã¹ããã€ãå ã«çœ®æ
åºãå°å ¥ãã䞊ã³ã«ïŒåã¯äºéçµåãå°å ¥ããã
ã¯é£œåãããæ¹æ³ã§ãç£æ¥çç£èŠæš¡ã§è£œé ãããŠ
ããããããã®åå¿äžã13âã¡ãã«åºã¯äžå€ã§ã
ãã
åŸæ¥ã18âã¢ã«ãã«âãšã¹ãã©ã³ååç©ã¯å®å
š
åæãå³ã¡ã¹ããã€ãéªšæ Œãããå°ããååãã
æ§æããåºçºç©è³ªã®é©åœãªéžæã«ãã18âã¢ã«ã
ã«åºã圢æããåææ¹æ³ã«ãã補é ããããç¹ã«
ã¹ããã€ãéªšæ Œäžã®å€ãã®é察称ççŽ ååã®ååš
ã«ãããå®å šåæã¯ãé·æéãèŠããé£ããæ¹æ³
ã§ãããåæã«é¢é£ããå€ãã®åé¡ããåºçºç©è³ª
ã®é©åœãªéžæåã³ç«äœç¹ç°çåå¿ã®ç¥èŠã«ãã解
決ãããããšã¯äºå®ã§ããããå€ãã®ç°æ§äœåé¢
å·¥çšåã³ç²Ÿè£œå·¥çšãäŸç¶ãšããŠå¿ èŠã§ããããã
ã«èµ·å ããäœåçåã³æ¯èŒçé«çµè²»ã®åé¡ãæ®ã
ããããã®ããšã¯ãæç®ã«èšèŒã®18âã¢ã«ãã«â
ãšã¹ãã©ã³ååç©ã®ææãªæ§è³ªåã³åŒ·åãªå¹åã«
ãããããããããã®ååç©ãå®éã«ã¯æ®ãã©é©
çšãããªãçç±ã§ãããã
åæãå³ã¡ã¹ããã€ãéªšæ Œãããå°ããååãã
æ§æããåºçºç©è³ªã®é©åœãªéžæã«ãã18âã¢ã«ã
ã«åºã圢æããåææ¹æ³ã«ãã補é ããããç¹ã«
ã¹ããã€ãéªšæ Œäžã®å€ãã®é察称ççŽ ååã®ååš
ã«ãããå®å šåæã¯ãé·æéãèŠããé£ããæ¹æ³
ã§ãããåæã«é¢é£ããå€ãã®åé¡ããåºçºç©è³ª
ã®é©åœãªéžæåã³ç«äœç¹ç°çåå¿ã®ç¥èŠã«ãã解
決ãããããšã¯äºå®ã§ããããå€ãã®ç°æ§äœåé¢
å·¥çšåã³ç²Ÿè£œå·¥çšãäŸç¶ãšããŠå¿ èŠã§ããããã
ã«èµ·å ããäœåçåã³æ¯èŒçé«çµè²»ã®åé¡ãæ®ã
ããããã®ããšã¯ãæç®ã«èšèŒã®18âã¢ã«ãã«â
ãšã¹ãã©ã³ååç©ã®ææãªæ§è³ªåã³åŒ·åãªå¹åã«
ãããããããããã®ååç©ãå®éã«ã¯æ®ãã©é©
çšãããªãçç±ã§ãããã
11βâããããã·â18âã¢ã«ãã«âãšã¹ãã©ã³
ååç©ã®æ°èŠãªè£œé æ¹æ³ã§ã¯ãåºçºç©è³ªãšããŠäž
èšã®åå¿æš¡åŒå³ã®éšååŒã§ç€ºããã11βâãã
ããã·â13âã¡ãã«âãŽãã³ååç©ãçšãããã®
ã¹ããã€ããéå°éã®æ¬¡äºæ²çŽ é žã¢ã·ã«ãšåå¿ã
ããçæãããšã¹ãã©ãâ18ïŒ11βâã©ã¯ãã³
ïŒïŒãååç©RXïŒïŒ²ïŒã¢ã«ãã«ãïŒMgBrãŸ
ãã¯LiïŒãšåå¿ãããããŸãã¯å æ°Žå解ããŠ11β
âããããã·â13âã«ã«ãã³é žååç©ïŒïŒãç
æããããã¢ã«ãã«ãªããŠã ååç©ãšåå¿ããã
çæãã11βâããããã·â18âã¢ã«ãã«â18â
ã±ãã³ïŒïŒã次ã«éå ã11βâããããã·â18
âã¢ã«ãã«âãšã¹ãã©ã³ååç©ïŒïŒã補é ã
ãã
ååç©ã®æ°èŠãªè£œé æ¹æ³ã§ã¯ãåºçºç©è³ªãšããŠäž
èšã®åå¿æš¡åŒå³ã®éšååŒã§ç€ºããã11βâãã
ããã·â13âã¡ãã«âãŽãã³ååç©ãçšãããã®
ã¹ããã€ããéå°éã®æ¬¡äºæ²çŽ é žã¢ã·ã«ãšåå¿ã
ããçæãããšã¹ãã©ãâ18ïŒ11βâã©ã¯ãã³
ïŒïŒãååç©RXïŒïŒ²ïŒã¢ã«ãã«ãïŒMgBrãŸ
ãã¯LiïŒãšåå¿ãããããŸãã¯å æ°Žå解ããŠ11β
âããããã·â13âã«ã«ãã³é žååç©ïŒïŒãç
æããããã¢ã«ãã«ãªããŠã ååç©ãšåå¿ããã
çæãã11βâããããã·â18âã¢ã«ãã«â18â
ã±ãã³ïŒïŒã次ã«éå ã11βâããããã·â18
âã¢ã«ãã«âãšã¹ãã©ã³ååç©ïŒïŒã補é ã
ãã
ãã®æ¹æ³ã«ããã11βâããããã·â18âã¢ã«
ãã«âãšã¹ãã©ã³ååç©ãç«äœç°æ§çåé¡ã®ãªã
ç°¡åã§äžã€ããããæ¹æ³ãçšãæŽã«ãåŸæ¥ã¯ãã
å°é£ãªå®å šåæã«ãã€ãŠã®ã¿å¯èœã§ãã€ãé«åç
ã以ãŠè£œé ãåŸããææã§ããã°ãäŸãã°ããã
ãã·ã«åºãããã²ã³åãããã¯ã¹ã«ããã«åã次
ã«ããã²ã³âãããã¯ã¹ã«ããã«ãªãã·åºã®éå
ã«ããé€å»ãŸãã¯ããããã·ã«åºãé žåã次ã«ãŠ
ãªã«ãïŒãã·ãŠããŒæ³ã«ãã圢æããã11âãªã
ãœåºã®éå ã«ãã11βâããããã·ã«åºãé€å»ã
ãããšãå¯èœã§ãããåŸã€ãŠãäŸãã°ã11βâã
ãããã·âÎïŒâãšã¹ãã¬ã³âïŒïŒ17âãžãªã³
ïŒïŒ17âãžãšãã¬ã³ã±ã¿ãŒã«ãæ¬çºææ¹æ³ã«ãã
11βâããããã·â18âã¡ãã«âÎïŒâãšã¹ãã¬
ã³âïŒïŒ17âãžãªã³ã«è»¢æãåŸããåèšã®11βâ
ããããã·ã«åºã®é€å»åã³ã17âãªããœåºãšã«ãª
ãŠã ã¢ã»ããªããšã®å ¬ç¥åå¿ã«ãã17αâãšãã
ã«â17βâããããã·ã«åºã®å°å ¥ã«ãããéèŠãª
âå®å šåæâååç©ãã«ã²ã¹ãã¬ã«ïŒïŒ17αâãš
ããã«â17βâããããã·â18âã¡ãã«âÎïŒâ
ãšã¹ãã¬ã³âïŒâãªã³ïŒã補é ãããããã®åå
ç©ã¯æå¹ãªããã²ã¹ããã³æ§ååç©ã§ãããå ¬ç¥
ã®åŸå£é¿åŠè¬ã«æŒããŠäœ¿çšãããŠããã
ãã«âãšã¹ãã©ã³ååç©ãç«äœç°æ§çåé¡ã®ãªã
ç°¡åã§äžã€ããããæ¹æ³ãçšãæŽã«ãåŸæ¥ã¯ãã
å°é£ãªå®å šåæã«ãã€ãŠã®ã¿å¯èœã§ãã€ãé«åç
ã以ãŠè£œé ãåŸããææã§ããã°ãäŸãã°ããã
ãã·ã«åºãããã²ã³åãããã¯ã¹ã«ããã«åã次
ã«ããã²ã³âãããã¯ã¹ã«ããã«ãªãã·åºã®éå
ã«ããé€å»ãŸãã¯ããããã·ã«åºãé žåã次ã«ãŠ
ãªã«ãïŒãã·ãŠããŒæ³ã«ãã圢æããã11âãªã
ãœåºã®éå ã«ãã11βâããããã·ã«åºãé€å»ã
ãããšãå¯èœã§ãããåŸã€ãŠãäŸãã°ã11βâã
ãããã·âÎïŒâãšã¹ãã¬ã³âïŒïŒ17âãžãªã³
ïŒïŒ17âãžãšãã¬ã³ã±ã¿ãŒã«ãæ¬çºææ¹æ³ã«ãã
11βâããããã·â18âã¡ãã«âÎïŒâãšã¹ãã¬
ã³âïŒïŒ17âãžãªã³ã«è»¢æãåŸããåèšã®11βâ
ããããã·ã«åºã®é€å»åã³ã17âãªããœåºãšã«ãª
ãŠã ã¢ã»ããªããšã®å ¬ç¥åå¿ã«ãã17αâãšãã
ã«â17βâããããã·ã«åºã®å°å ¥ã«ãããéèŠãª
âå®å šåæâååç©ãã«ã²ã¹ãã¬ã«ïŒïŒ17αâãš
ããã«â17βâããããã·â18âã¡ãã«âÎïŒâ
ãšã¹ãã¬ã³âïŒâãªã³ïŒã補é ãããããã®åå
ç©ã¯æå¹ãªããã²ã¹ããã³æ§ååç©ã§ãããå ¬ç¥
ã®åŸå£é¿åŠè¬ã«æŒããŠäœ¿çšãããŠããã
æ¬çºææ¹æ³ã§è£œé ããã11βâããããã·â18
âã¢ã«ãã«ååç©ã¯æŽã«ãæç®ã«èšèŒãããŠãã
è¬çåŠäžéèŠãª11â眮æ18âã¢ã«ãã«ååç©ã®åº
çºç©è³ªãšããŠéèŠã§ãããåèšååç©ã¯äŸãã°ã
11βïŒ18âãžã¡ãã«âïŒ11βâããã²ã³â18âã¡
ãã«âã11ïŒ11âã¡ãã¬ã³â18âã¡ãã«âåã³11
βâã¡ããã·ã¡ãã«â18âã¡ãã«âãšã¹ãã©ã³å
åç©ã§ããïŒäŸãã°åé¿èšéŠç¹èš±ç¬¬73ïŒ9161å·ã
åç §ããããïŒã
âã¢ã«ãã«ååç©ã¯æŽã«ãæç®ã«èšèŒãããŠãã
è¬çåŠäžéèŠãª11â眮æ18âã¢ã«ãã«ååç©ã®åº
çºç©è³ªãšããŠéèŠã§ãããåèšååç©ã¯äŸãã°ã
11βïŒ18âãžã¡ãã«âïŒ11βâããã²ã³â18âã¡
ãã«âã11ïŒ11âã¡ãã¬ã³â18âã¡ãã«âåã³11
βâã¡ããã·ã¡ãã«â18âã¡ãã«âãšã¹ãã©ã³å
åç©ã§ããïŒäŸãã°åé¿èšéŠç¹èš±ç¬¬73ïŒ9161å·ã
åç §ããããïŒã
åºçºç©è³ªãšããŠäœ¿çšããã11βâããããã·â
13âã¡ãã«âãŽãã³ååç©ãç°æ§é å ã®å¥ã®äœçœ®
ã«çœ®æåºãæããŠããŠããããäŸãã°ãïŒåã³ïŒ
åã¯17âäœã«ãªããœåºïŒåã³å¥œããã¯ãããã®å®
èœåºèªå°äœïŒãïŒïŒïŒïŒïŒïŒïŒïŒïŒïŒïŒïŒïŒïŒ15
åã³ïŒåã¯16âäœã«éé¢ãšã¹ãã«åãããã¯ãšãŒ
ãã«åããããã·ã«åºïŒéé¢ããããã·ã«åºã¯æ¬
çºææ¹æ³äžãä¿è·ãããã®ã奜ããïŒãïŒïŒïŒïŒ
ïŒïŒïŒïŒ11αåã³ïŒåã¯16âäœã«ã¢ã«ãã«åºäŸã
ã°ã¡ãã«åºãããã¯ãšãã«åºã䞊ã³ã«ïŒåã¯17β
âäœã®éé¢ãšã¹ãã«åãããã¯ãšãŒãã«åããã
ãã·ã«åºã®æ¬¡ã®17αâäœã«ã¡ãã«ããšãã«ãã€ãœ
ãããã«ãããã«ãããã¯ã€ãœããããã«ã®åŠã
ççŽ ååïŒãïŒã®é£œåãããã¯äžé£œåã¢ã«ãã«åº
ãæããŠããŠãããããªããœåºã®å®èœåºèªå°äœãš
ã¯ã±ã¿ãŒã«åãªããœåºãŸãã¯ãã®ãšããŒã«èªå°äœ
ã«è»¢æããããªããœåºãäŸãã°ãšããŒã«ãšãŒãã«
ãããã¯ãšããŒã«ãšã¹ãã«ãæå³ãããæŽã«åºçº
ç©è³ªããäŸãã°ïŒïŒïŒâïŒïŒïŒïŒâãŸãã¯ïŒïŒ10
âäœã«äºéçµåãæããŠããŠãããã
13âã¡ãã«âãŽãã³ååç©ãç°æ§é å ã®å¥ã®äœçœ®
ã«çœ®æåºãæããŠããŠããããäŸãã°ãïŒåã³ïŒ
åã¯17âäœã«ãªããœåºïŒåã³å¥œããã¯ãããã®å®
èœåºèªå°äœïŒãïŒïŒïŒïŒïŒïŒïŒïŒïŒïŒïŒïŒïŒïŒ15
åã³ïŒåã¯16âäœã«éé¢ãšã¹ãã«åãããã¯ãšãŒ
ãã«åããããã·ã«åºïŒéé¢ããããã·ã«åºã¯æ¬
çºææ¹æ³äžãä¿è·ãããã®ã奜ããïŒãïŒïŒïŒïŒ
ïŒïŒïŒïŒ11αåã³ïŒåã¯16âäœã«ã¢ã«ãã«åºäŸã
ã°ã¡ãã«åºãããã¯ãšãã«åºã䞊ã³ã«ïŒåã¯17β
âäœã®éé¢ãšã¹ãã«åãããã¯ãšãŒãã«åããã
ãã·ã«åºã®æ¬¡ã®17αâäœã«ã¡ãã«ããšãã«ãã€ãœ
ãããã«ãããã«ãããã¯ã€ãœããããã«ã®åŠã
ççŽ ååïŒãïŒã®é£œåãããã¯äžé£œåã¢ã«ãã«åº
ãæããŠããŠãããããªããœåºã®å®èœåºèªå°äœãš
ã¯ã±ã¿ãŒã«åãªããœåºãŸãã¯ãã®ãšããŒã«èªå°äœ
ã«è»¢æããããªããœåºãäŸãã°ãšããŒã«ãšãŒãã«
ãããã¯ãšããŒã«ãšã¹ãã«ãæå³ãããæŽã«åºçº
ç©è³ªããäŸãã°ïŒïŒïŒâïŒïŒïŒïŒâãŸãã¯ïŒïŒ10
âäœã«äºéçµåãæããŠããŠãããã
奜ããåºçºç©è³ªã¯ãåŒ
ãåŒäžãR1ã¯H2ïŒïŒšïŒOR3ïŒïŒïŒ¯ãŸãã¯ã±ã¿ãŒ
ã«åãR2ã¯ïŒ¯ïŒã±ã¿ãŒã«åïŒïŒšïŒOR4ïŒãŸã
ã¯ïŒÎ±âã¢ã«ãã«ïŒïŒÎ²OR4ïŒïœã¢ã«ãã«åºã¯ççŽ
ååïŒãïŒãæããŠããR3åã³R4ã¯ïŒšãŸãã¯ã
ã¢ã·ã«ãããã¯ã¢ã«ãã«å¥œããã¯ã¢ã»ãã«ã®ãã
ãªä¿è·åºïœã§ããïŒïŒïŒãŸãã¯ïŒïŒïŒâäœã«ïŒå
ã®äºéçµåãååšãããã§ç€ºããã11βâããã
ãã·â13âã¡ãã«âãŽãã³ååç©ã§ããã
ã«åãR2ã¯ïŒ¯ïŒã±ã¿ãŒã«åïŒïŒšïŒOR4ïŒãŸã
ã¯ïŒÎ±âã¢ã«ãã«ïŒïŒÎ²OR4ïŒïœã¢ã«ãã«åºã¯ççŽ
ååïŒãïŒãæããŠããR3åã³R4ã¯ïŒšãŸãã¯ã
ã¢ã·ã«ãããã¯ã¢ã«ãã«å¥œããã¯ã¢ã»ãã«ã®ãã
ãªä¿è·åºïœã§ããïŒïŒïŒãŸãã¯ïŒïŒïŒâäœã«ïŒå
ã®äºéçµåãååšãããã§ç€ºããã11βâããã
ãã·â13âã¡ãã«âãŽãã³ååç©ã§ããã
åºçºç©è³ªã®ç¹å®äŸã¯ã11βâããããã·âÎïŒ
âãšã¹ãã¬ã³âïŒïŒ17âãžãªã³ïŒïŒ17âãžãšãã¬
ã³ã±ã¿ãŒã«ïŒ11βâ17βâãžããããã·âÎïŒâ
ãšã¹ãã¬ã³âïŒâãªã³ïŒâãšãã¬ã³ã±ã¿ãŒã«17â
é ¢é žå¡©ïŒ11βâããããã·âÎïŒâãšã¹ãã¬ã³â
17âãªã³17âãšãã¬ã³ã±ã¿ãŒã«ïŒÎïŒâãšã¹ãã¬
ã³â11βïŒ17βâãžãªãŒã«17âé ¢é žå¡©ïŒ11βâã
ãããã·âÎïŒâãšã¹ãã¬ã³âïŒïŒ17âãžãªã³ïŒ
ïŒÎ²ïŒ11βâãžããããã·âÎïŒâãšã¹ãã¬ã³â
17âãªã³ïŒâé ¢é žå¡©17âãšãã¬ã³ã±ã¿ãŒã«ïŒ11β
âããããã·âÎïŒâãšã¹ãã¬ã³â17âãªã³17â
ãšãã¬ã³ã±ã¿ãŒã«ïŒÎïŒâãšã¹ãã¬ã³â11βïŒ17
βâãžãªãŒã«17âé ¢é žå¡©ïŒ11βïŒ17βâãžããã
ãã·â17αâã¡ãã«âÎïŒâãšã¹ãã¬ã³âïŒâãª
ã³ïŒâãšãã¬ã³ã±ã¿ãŒã«17âé ¢é žå¡©åã³å¯Ÿå¿ãã
17αâãšãã«ååç©çã§ããã
âãšã¹ãã¬ã³âïŒïŒ17âãžãªã³ïŒïŒ17âãžãšãã¬
ã³ã±ã¿ãŒã«ïŒ11βâ17βâãžããããã·âÎïŒâ
ãšã¹ãã¬ã³âïŒâãªã³ïŒâãšãã¬ã³ã±ã¿ãŒã«17â
é ¢é žå¡©ïŒ11βâããããã·âÎïŒâãšã¹ãã¬ã³â
17âãªã³17âãšãã¬ã³ã±ã¿ãŒã«ïŒÎïŒâãšã¹ãã¬
ã³â11βïŒ17βâãžãªãŒã«17âé ¢é žå¡©ïŒ11βâã
ãããã·âÎïŒâãšã¹ãã¬ã³âïŒïŒ17âãžãªã³ïŒ
ïŒÎ²ïŒ11βâãžããããã·âÎïŒâãšã¹ãã¬ã³â
17âãªã³ïŒâé ¢é žå¡©17âãšãã¬ã³ã±ã¿ãŒã«ïŒ11β
âããããã·âÎïŒâãšã¹ãã¬ã³â17âãªã³17â
ãšãã¬ã³ã±ã¿ãŒã«ïŒÎïŒâãšã¹ãã¬ã³â11βïŒ17
βâãžãªãŒã«17âé ¢é žå¡©ïŒ11βïŒ17βâãžããã
ãã·â17αâã¡ãã«âÎïŒâãšã¹ãã¬ã³âïŒâãª
ã³ïŒâãšãã¬ã³ã±ã¿ãŒã«17âé ¢é žå¡©åã³å¯Ÿå¿ãã
17αâãšãã«ååç©çã§ããã
11βâããããã·ã«åºããããªãå
¬ç¥ã®ãšã¹ã
ã©ã³ååç©ãæ¬çºææ¹æ³ã®åºçºç©è³ªã«å®¹æã«è»¢æ
ãåŸããäŸãã°ã¢ã¹ãã«ã®ã«ã¹ã»ãªã¯ã©ã»ãŠã¹
Aspergillus ochraceusïŒãªãŸãã¹ã»ãã°ãªã«ã³
ã¹Rhizopus nigricansãŸãã¯ãã¹ã¿ããã¢ã»ãã€
ãšãPestalotia royenaã®ãããªåŸ®çç©ãçšããŠ
埮çç©åŠçæ¹æ³ã§11αâããããã·ã«åºãå°å ¥
ãã次ã«äŸãã°ã¯ãã é žã«ãã11αâããããã·
ã«åºãé žåããŠ11âã±ãã³ã圢æãããã®åŸäŸã
ã°NaBH4ã«ããéå ããŠ11âã±ãã³ã11βâã
ãããã·âãšã¹ãã©ã³ååç©ã«è»¢æããããã®ã
ãã«ããŠäŸãã°19âãã«âãã¹ãã¹ããã³ã埮ç
ç©åŠçæ¹æ³ã§11αâããããã·â19âãã«âãã¹
ãã¹ããã³ã«è»¢æããã®ååç©ããžãšãŒã³ãºæ°è©Š
è¬ãšåå¿ãããŠå¯Ÿå¿ãã11ïŒ17âãžã±ãã³ïŒÎïŒ
âãšã¹ãã¬ã³âïŒïŒ11ïŒ17âããªãªã³ïŒã圢æ
ãã次ã«ãã®ïŒïŒ11ïŒ17âããªã±ãã³ã®ïŒâåã³
17âãªããœåºãã±ã¿ãŒã«ã®åœ¢ç¶ã§ä¿è·ããŠãã
NaBH4ã§éå ããŠ11βâããããã·âÎïŒâãš
ã¹ãã¬ã³âïŒïŒ17âãžãªã³ïŒïŒ17âãžã±ã¿ãŒã«ã«
転æããã
ã©ã³ååç©ãæ¬çºææ¹æ³ã®åºçºç©è³ªã«å®¹æã«è»¢æ
ãåŸããäŸãã°ã¢ã¹ãã«ã®ã«ã¹ã»ãªã¯ã©ã»ãŠã¹
Aspergillus ochraceusïŒãªãŸãã¹ã»ãã°ãªã«ã³
ã¹Rhizopus nigricansãŸãã¯ãã¹ã¿ããã¢ã»ãã€
ãšãPestalotia royenaã®ãããªåŸ®çç©ãçšããŠ
埮çç©åŠçæ¹æ³ã§11αâããããã·ã«åºãå°å ¥
ãã次ã«äŸãã°ã¯ãã é žã«ãã11αâããããã·
ã«åºãé žåããŠ11âã±ãã³ã圢æãããã®åŸäŸã
ã°NaBH4ã«ããéå ããŠ11âã±ãã³ã11βâã
ãããã·âãšã¹ãã©ã³ååç©ã«è»¢æããããã®ã
ãã«ããŠäŸãã°19âãã«âãã¹ãã¹ããã³ã埮ç
ç©åŠçæ¹æ³ã§11αâããããã·â19âãã«âãã¹
ãã¹ããã³ã«è»¢æããã®ååç©ããžãšãŒã³ãºæ°è©Š
è¬ãšåå¿ãããŠå¯Ÿå¿ãã11ïŒ17âãžã±ãã³ïŒÎïŒ
âãšã¹ãã¬ã³âïŒïŒ11ïŒ17âããªãªã³ïŒã圢æ
ãã次ã«ãã®ïŒïŒ11ïŒ17âããªã±ãã³ã®ïŒâåã³
17âãªããœåºãã±ã¿ãŒã«ã®åœ¢ç¶ã§ä¿è·ããŠãã
NaBH4ã§éå ããŠ11βâããããã·âÎïŒâãš
ã¹ãã¬ã³âïŒïŒ17âãžãªã³ïŒïŒ17âãžã±ã¿ãŒã«ã«
転æããã
äŸãã°åŸ®çç©ã¯ã«ãã©ãªã¢ã»ã«ãã¿
Curvularialunataãšå ±ã«åŸ®çç©åŠçæ¹æ³ã§11βâ
ããããã·ã«åºãçŽæ¥ã«å°å ¥ããŠãããã
Curvularialunataãšå ±ã«åŸ®çç©åŠçæ¹æ³ã§11βâ
ããããã·ã«åºãçŽæ¥ã«å°å ¥ããŠãããã
æ¬çºææ¹æ³ã«ããã°11βâããããã·â13âã¡
ãã«âãŽãã³ååç©ïŒïŒãéå°éã®æ¬¡äºæ²çŽ é ž
ã¢ã·ã«ãšåå¿ãããšã¹ãã©ãâ18ïŒ11βâã©ã¯ã
ã³ïŒïŒãçæãããééå±ã®ã¢ã·ã«åç©äŸãã°
åšæç³»ã®ç¬¬ïŒã第ïŒåã³ç¬¬ïŒäºå±ã®éå±ã®é ¢é ž
å¡©ãããããªã³é žå¡©ãŸãã¯å®æ¯éŠé žå¡©äŸãã°ã¢ã·
ã«åéãã¢ã·ã«åæ°ŽéãŸãã¯ã¢ã·ã«åéãšæ²çŽ ãš
ãçšããã®å Žã§æ¬¡äºæ²çŽ é žã¢ã·ã«ã補é ããã®ã
奜ããã奜ããã¯åã¢ã·ã«åéäŸãã°åé ¢é žéã
䜿çšãæ²çŽ ãšå ±ã«ãžã¢ã·ã«åéåã³æ¬¡äºæ²çŽ é žã¢
ã·ã«ãçæãããã次äºæ²çŽ é žã¢ã·ã«ã11βâã
ãããã·ã«åºãå ã11βâ次äºæ²çŽ é žå¡©åºã«è»¢æ
ãã次ã«ååå 転äœã«ãã11βâããããã·â13
âãšãŒãã¡ãã«ååç©ã圢æããããéå°éã®æ¬¡
äºæ²çŽ é žã¢ã·ã«ã«ãã13â眮æãå埩ããããã«
ããå€å18âãšãŒãâ11βïŒ18âãšããã·ããŸã
ã¯11βâããããã·â18ïŒ18âãžãšãŒãååç©ã
çµç±ããŠæçµçã«ãšã¹ãã©ãâ18ïŒ11βâã©ã¯ã
ã³ïŒïŒã圢æãããã
ãã«âãŽãã³ååç©ïŒïŒãéå°éã®æ¬¡äºæ²çŽ é ž
ã¢ã·ã«ãšåå¿ãããšã¹ãã©ãâ18ïŒ11βâã©ã¯ã
ã³ïŒïŒãçæãããééå±ã®ã¢ã·ã«åç©äŸãã°
åšæç³»ã®ç¬¬ïŒã第ïŒåã³ç¬¬ïŒäºå±ã®éå±ã®é ¢é ž
å¡©ãããããªã³é žå¡©ãŸãã¯å®æ¯éŠé žå¡©äŸãã°ã¢ã·
ã«åéãã¢ã·ã«åæ°ŽéãŸãã¯ã¢ã·ã«åéãšæ²çŽ ãš
ãçšããã®å Žã§æ¬¡äºæ²çŽ é žã¢ã·ã«ã補é ããã®ã
奜ããã奜ããã¯åã¢ã·ã«åéäŸãã°åé ¢é žéã
䜿çšãæ²çŽ ãšå ±ã«ãžã¢ã·ã«åéåã³æ¬¡äºæ²çŽ é žã¢
ã·ã«ãçæãããã次äºæ²çŽ é žã¢ã·ã«ã11βâã
ãããã·ã«åºãå ã11βâ次äºæ²çŽ é žå¡©åºã«è»¢æ
ãã次ã«ååå 転äœã«ãã11βâããããã·â13
âãšãŒãã¡ãã«ååç©ã圢æããããéå°éã®æ¬¡
äºæ²çŽ é žã¢ã·ã«ã«ãã13â眮æãå埩ããããã«
ããå€å18âãšãŒãâ11βïŒ18âãšããã·ããŸã
ã¯11βâããããã·â18ïŒ18âãžãšãŒãååç©ã
çµç±ããŠæçµçã«ãšã¹ãã©ãâ18ïŒ11βâã©ã¯ã
ã³ïŒïŒã圢æãããã
ãšã¹ãã©ãâ18ïŒ11βâã©ã¯ãã³ã¯ãäŸãã°åº
çºç©è³ªãè©Šè¬ã«å¯ŸããŠäžæŽ»æ§ã®æº¶åªäŸãã°ã·ã¯ã
ãããµã³ãããã¯ã¡ãã«ã·ã¯ããããµã³ã®ãããª
çåæ°ŽçŽ ãŸãã¯ãžã¯ããã¡ã¿ã³ãåå¡©åççŽ ãã
ãã¯ãããµã¯ãããã¿ãžãšã³ã®ãããªå¡©çŽ åçå
æ°ŽçŽ äžã«æº¶è§£ãŸãã¯æžæ¿ãããåé ¢é žéã®ãããª
åã¢ã·ã«åéåã³æ²çŽ åã³ä»»æã«çé žã«ã«ã·ãŠã
ã®ãããªåŒ±å¡©åºãæ·»å ããåå¿æ··åç©ãå ç±æ¹æ
ããŠè£œé ããããåžžå§ãŸãã¯å å§äžã§äŸãã°æº¶åª
ã®æ²žéš°æž©åºŠã§éæµãã€ã€åå¿ãçèµ·ãåŸããåå¿
ç¶ç¶æéã¯ç¹ã«ã枩床åã³äœ¿çšæº¶åªã«ãã決å®ã
ãããã·ã¯ããããµã³äžã§æ²çŽ ãšåé ¢é žéãšãé
æµããå Žåãåå¿ã¯éåžžïŒæé以å ã«å®äºããã
åå¿æž©åºŠã¯éåžž50ã150âã§ããã
çºç©è³ªãè©Šè¬ã«å¯ŸããŠäžæŽ»æ§ã®æº¶åªäŸãã°ã·ã¯ã
ãããµã³ãããã¯ã¡ãã«ã·ã¯ããããµã³ã®ãããª
çåæ°ŽçŽ ãŸãã¯ãžã¯ããã¡ã¿ã³ãåå¡©åççŽ ãã
ãã¯ãããµã¯ãããã¿ãžãšã³ã®ãããªå¡©çŽ åçå
æ°ŽçŽ äžã«æº¶è§£ãŸãã¯æžæ¿ãããåé ¢é žéã®ãããª
åã¢ã·ã«åéåã³æ²çŽ åã³ä»»æã«çé žã«ã«ã·ãŠã
ã®ãããªåŒ±å¡©åºãæ·»å ããåå¿æ··åç©ãå ç±æ¹æ
ããŠè£œé ããããåžžå§ãŸãã¯å å§äžã§äŸãã°æº¶åª
ã®æ²žéš°æž©åºŠã§éæµãã€ã€åå¿ãçèµ·ãåŸããåå¿
ç¶ç¶æéã¯ç¹ã«ã枩床åã³äœ¿çšæº¶åªã«ãã決å®ã
ãããã·ã¯ããããµã³äžã§æ²çŽ ãšåé ¢é žéãšãé
æµããå Žåãåå¿ã¯éåžžïŒæé以å ã«å®äºããã
åå¿æž©åºŠã¯éåžž50ã150âã§ããã
åå¿æ··åç©ã«å¯èŠå
ç·åã³ïŒåã¯çŽ«å€å
ç·ãç
§
å°ããããšã«ããåå¿ãä¿é²ãåŸããããããªã
ã奜ããã¯åå¿ä¿é²ã®ç®çã§åå¿æ··åç©ã«ã©ãžã«
ã«éå§å€ãæ·»å ãããäŸãã°ã¢ãŸã€ãœããããžã
ããªã«ã®æ·»å ãåå¿ç¶ç¶æéã«å¥œãã圱é¿ãäžã
ãããšãå€æãããã©ãžã«ã«éå§å€ã®éã¯å³å¯ã«
確å®ãããªããã¹ããã€ãïŒã°ã©ã ã¢ã«ã«ã€ã
0.1ã0.25ã°ã©ã ã¢ã«ã䜿çšãããšè¯å¥œãªçµæã
åŸãããã
å°ããããšã«ããåå¿ãä¿é²ãåŸããããããªã
ã奜ããã¯åå¿ä¿é²ã®ç®çã§åå¿æ··åç©ã«ã©ãžã«
ã«éå§å€ãæ·»å ãããäŸãã°ã¢ãŸã€ãœããããžã
ããªã«ã®æ·»å ãåå¿ç¶ç¶æéã«å¥œãã圱é¿ãäžã
ãããšãå€æãããã©ãžã«ã«éå§å€ã®éã¯å³å¯ã«
確å®ãããªããã¹ããã€ãïŒã°ã©ã ã¢ã«ã«ã€ã
0.1ã0.25ã°ã©ã ã¢ã«ã䜿çšãããšè¯å¥œãªçµæã
åŸãããã
é«åçãåŸãããã«ãåå¿æ··åç©äžã®æ²çŽ ã¯ã
ã¹ããã€ãïŒã°ã©ã ã¢ã«ã«ã€ãI2ãšããŠå°ããšã
1.5ã°ã©ã ã¢ã«ã§ããéåžžã¯ïŒã°ã©ã ã¢ã«æªæºãš
ãªãéã§ãªããã°ãªããªããåã¢ã·ã«åéã®é
ïŒã°ã©ã ã¢ã«ïŒã¯å°ããšãI2ã®éã«çãããæŽã«
ããå€ãããšã奜ãããéåžžI21ã°ã©ã ã¢ã«ã«ã€
ãåã¢ã·ã«åé1.5ãïŒã°ã©ã ã¢ã«ã䜿çšããã
ã¹ããã€ãïŒã°ã©ã ã¢ã«ã«ã€ãI2ãšããŠå°ããšã
1.5ã°ã©ã ã¢ã«ã§ããéåžžã¯ïŒã°ã©ã ã¢ã«æªæºãš
ãªãéã§ãªããã°ãªããªããåã¢ã·ã«åéã®é
ïŒã°ã©ã ã¢ã«ïŒã¯å°ããšãI2ã®éã«çãããæŽã«
ããå€ãããšã奜ãããéåžžI21ã°ã©ã ã¢ã«ã«ã€
ãåã¢ã·ã«åé1.5ãïŒã°ã©ã ã¢ã«ã䜿çšããã
åå¿æéã¯ç¢ºå®çãªãã®ã§ã¯ãªã䜿çšæ²çŽ ã®é
ã«åºããŠæ±ºå®ããããI2ã®éå°éã®å¢å ã«æ¯äŸã
ãŠåå¿æéãççž®ãåŸãã
ã«åºããŠæ±ºå®ããããI2ã®éå°éã®å¢å ã«æ¯äŸã
ãŠåå¿æéãççž®ãåŸãã
沞隰ã·ã¯ããããµã³äžã§ã©ãžã«ã«éå§å€ãååš
ããã¹ããã€ãïŒã°ã©ã ã¢ã«ã«ã€ãæ²çŽ 1.5ã2.0
ã°ã©ã ã¢ã«ã䜿çšããŠåå¿ãçèµ·ããå Žåãåå¿
æéã¯çŽ10ã30åéã§ãããã
ããã¹ããã€ãïŒã°ã©ã ã¢ã«ã«ã€ãæ²çŽ 1.5ã2.0
ã°ã©ã ã¢ã«ã䜿çšããŠåå¿ãçèµ·ããå Žåãåå¿
æéã¯çŽ10ã30åéã§ãããã
æ¬çºææ¹æ³ã«ããã°ã次ã«ãšã¹ãã©ãâ18ïŒ11
βâã©ã¯ãã³ïŒïŒãååç©RXïŒåŒäžãã¯ã¢
ã«ãã«ãã¯MgBrãŸãã¯Liã§ããïŒãšåå¿ãã
ããååç©RXäžã®ã¢ã«ãã«åºã¯å¥œããã¯ççŽ å
åïŒãïŒã®ã¢ã«ãã«åºã§ãããååç©RXã®äŸ
ã¯ãèåã¡ãã«ãã°ãã·ãŠã ãã¡ãã«ãªããŠã ã
èåãšãã«ãã°ãã·ãŠã ããšãã«ãªããŠã ãèå
ãããã«ãã°ãã·ãŠã åã³ããã«ãªããŠã ã§ã
ãã
βâã©ã¯ãã³ïŒïŒãååç©RXïŒåŒäžãã¯ã¢
ã«ãã«ãã¯MgBrãŸãã¯Liã§ããïŒãšåå¿ãã
ããååç©RXäžã®ã¢ã«ãã«åºã¯å¥œããã¯ççŽ å
åïŒãïŒã®ã¢ã«ãã«åºã§ãããååç©RXã®äŸ
ã¯ãèåã¡ãã«ãã°ãã·ãŠã ãã¡ãã«ãªããŠã ã
èåãšãã«ãã°ãã·ãŠã ããšãã«ãªããŠã ãèå
ãããã«ãã°ãã·ãŠã åã³ããã«ãªããŠã ã§ã
ãã
ãšã¹ãã©ãâ18ïŒ11βâã©ã¯ãã³ãšååç©RX
ãšã®åå¿ã¯ãç¡æ°Žç¶æ ã®äžæŽ»æ§æº¶åªäŸãã°ç¡æ°Žãš
ãŒãã«ãŸãã¯ç¡æ°Žãã«ãšã³ãŸãã¯äž¡è ã®æ··åç©äž
ã§çèµ·ããããåå¿åŸãåå¿æ··åç©ããæ°Žãåžé
é žãŸãã¯NH4Cl溶液ã®ãããªãããã³äŸäžäœã§é
ãã«åŠçããæŽã«åŠçå·¥çšãç¶ç¶ããã奜ããã
ããã³äŸäžäœã¯æ°Žã§ããããã®æ¹æ³ã§ãšã¹ãã©ã
â18ïŒ11βâã©ã¯ãã³ãã11βâããããã·â18
âã¢ã«ãã«â18âã±ãã³ïŒïŒã補é ãããã
ãšã®åå¿ã¯ãç¡æ°Žç¶æ ã®äžæŽ»æ§æº¶åªäŸãã°ç¡æ°Žãš
ãŒãã«ãŸãã¯ç¡æ°Žãã«ãšã³ãŸãã¯äž¡è ã®æ··åç©äž
ã§çèµ·ããããåå¿åŸãåå¿æ··åç©ããæ°Žãåžé
é žãŸãã¯NH4Cl溶液ã®ãããªãããã³äŸäžäœã§é
ãã«åŠçããæŽã«åŠçå·¥çšãç¶ç¶ããã奜ããã
ããã³äŸäžäœã¯æ°Žã§ããããã®æ¹æ³ã§ãšã¹ãã©ã
â18ïŒ11βâã©ã¯ãã³ãã11βâããããã·â18
âã¢ã«ãã«â18âã±ãã³ïŒïŒã補é ãããã
ãšã¹ãã©ãâ18ïŒ11βâã©ã¯ãã³ïŒïŒã11β
âããããã·â18âã¢ã«ãã«â18âãªããœâåå
ç©ïŒïŒã«è»¢æããå¥ã®æ¹æ³ã«ããã°ãäŸãã°ã¡
ã¿ããŒã«äžã®æ°Žé žåãããªãŠã åžé溶液äžã§ã©ã¯
ãã³ãéãã«å ç±ããããšã«ããå ãã©ã¯ãã³ã
å æ°Žå解ããŠ11βâããããã·â13âã«ã«ãã³é ž
ïŒïŒãçæããã次ã«11βâããããã·â13â
ã«ã«ãã³é žãäŸãã°ã¡ãã«ãªããŠã ããšãã«ãªã
ãŠã ãŸãã¯ããã«ãªããŠã ã®ãããªã¢ã«ãã«ãªã
ãŠã ååç©ãšåå¿ããããäŸãã°ç¡æ°Žç¶æ ã®ãã
ã©ããããã©ã³ã®ãããªäžæŽ»æ§æº¶åªäžã§å¥œããã¯
ïŒâãšããäœæž©ã§åå¿ãçèµ·ãããããã®æ¹æ³ã«
ãã11βâããããã·â18âã¢ã«ãã«â18âã±ã
ã³ïŒïŒãé«åçã§è£œé ãããã
âããããã·â18âã¢ã«ãã«â18âãªããœâåå
ç©ïŒïŒã«è»¢æããå¥ã®æ¹æ³ã«ããã°ãäŸãã°ã¡
ã¿ããŒã«äžã®æ°Žé žåãããªãŠã åžé溶液äžã§ã©ã¯
ãã³ãéãã«å ç±ããããšã«ããå ãã©ã¯ãã³ã
å æ°Žå解ããŠ11βâããããã·â13âã«ã«ãã³é ž
ïŒïŒãçæããã次ã«11βâããããã·â13â
ã«ã«ãã³é žãäŸãã°ã¡ãã«ãªããŠã ããšãã«ãªã
ãŠã ãŸãã¯ããã«ãªããŠã ã®ãããªã¢ã«ãã«ãªã
ãŠã ååç©ãšåå¿ããããäŸãã°ç¡æ°Žç¶æ ã®ãã
ã©ããããã©ã³ã®ãããªäžæŽ»æ§æº¶åªäžã§å¥œããã¯
ïŒâãšããäœæž©ã§åå¿ãçèµ·ãããããã®æ¹æ³ã«
ãã11βâããããã·â18âã¢ã«ãã«â18âã±ã
ã³ïŒïŒãé«åçã§è£œé ãããã
æåŸã«11βâããããã·â18âã¢ã«ãã«â18â
ã±ãã³ïŒïŒã11βâããããã·â18âã¢ã«ãã«
ååç©ïŒïŒã«è»¢æããããŠãªã«ãïŒãã·ãŠããŒ
æ³ã«ãã18âãªããœåºã®éå ãå¹æçã«çèµ·ãã
ã«ã«ããã«ååç©ããã®ããã©ãŸã³ãŸãã¯ã»ãã«
ã«ããŸã³ã«è»¢æããã®ããã©ãŸã³ãŸãã¯ã»ãã«ã«
ããŸã³ãã¢ã«ã«ãªæ§ç¶æ ã§å解ãããäŸãã°ãã
ãªãŠã ãšããã·ãã®ãããªã¢ã«ã³ãã·ããŸãã¯æ°Ž
é žåã«ãªãŠã ã®è£å©ã«ããã¢ã«ã«ãªæ§å解ãçèµ·
ããã奜ãŸããã¯ãã¢ã³ãã³ãã³å€åœ¢æ³ã䜿çš
ãããžãšãã¬ã³ã°ãªã³ãŒã«ã®ãããªé«æ²žç¹æº¶åªã
çšããŠ100âããé«æž©ã§åå¿ãçèµ·ãåå¿äžã«åœ¢
æãããæ°Žãèžçé€å»ããã
ã±ãã³ïŒïŒã11βâããããã·â18âã¢ã«ãã«
ååç©ïŒïŒã«è»¢æããããŠãªã«ãïŒãã·ãŠããŒ
æ³ã«ãã18âãªããœåºã®éå ãå¹æçã«çèµ·ãã
ã«ã«ããã«ååç©ããã®ããã©ãŸã³ãŸãã¯ã»ãã«
ã«ããŸã³ã«è»¢æããã®ããã©ãŸã³ãŸãã¯ã»ãã«ã«
ããŸã³ãã¢ã«ã«ãªæ§ç¶æ ã§å解ãããäŸãã°ãã
ãªãŠã ãšããã·ãã®ãããªã¢ã«ã³ãã·ããŸãã¯æ°Ž
é žåã«ãªãŠã ã®è£å©ã«ããã¢ã«ã«ãªæ§å解ãçèµ·
ããã奜ãŸããã¯ãã¢ã³ãã³ãã³å€åœ¢æ³ã䜿çš
ãããžãšãã¬ã³ã°ãªã³ãŒã«ã®ãããªé«æ²žç¹æº¶åªã
çšããŠ100âããé«æž©ã§åå¿ãçèµ·ãåå¿äžã«åœ¢
æãããæ°Žãèžçé€å»ããã
11βâããããã·â18âã¢ã«ãã«â18âã±ãã³
ïŒïŒã¯æŽã«ãç°æ§äœã®ç°ç¶ããã¢ã»ã¿ãŒã«
ïŒïŒã®åœ¢ç¶ã§ååšãåŸããåŸã€ãŠãšã¹ãã©ãâ
18ïŒ11βâã©ã¯ãã³ïŒïŒãšååç©RXãšã®åå¿
ã¯ç°ç¶ããã¢ã»ã¿ãŒã«ïŒïŒãçµç±ããŠé²è¡ãåŸ
ãããã®ç°ç¶ããã¢ã»ã¿ãŒã«ïŒïŒåã³ãåŸã€ãŠ
11βâããããã·â18âã¢ã«ãã«â18âã±ãã³
ïŒïŒã¯äŸãã°ã·ãªã«ã²ã«ã®è£å©ã«ãã容æã«è±
æ°ŽãããŠ18ïŒ18âã¢ã«ããªãã³â11βïŒ18âãªã
ã·ãååç©ïŒïŒãçæãåŸãããã®ååç©ã11
βâããããã·â18âã¢ã«ãã«â18âã±ãã³ãšå
æ§ã®æ¹æ³ã§éå ã11βâããããã·â18âã¢ã«ã
ã«ååç©ïŒïŒã補é ãåŸããåŸã€ãŠ11βâãã
ããã·â18âã¢ã«ãã«â18âã±ãã³ïŒïŒã®éå
ã«ãã11βâããããã·â18âã¢ã«ãã«ååç©ã
補é ããå·¥çšã¯ã11βâããããã·â18âã¢ã«ã
ã«â18âã±ãã³ïŒïŒãè±æ°Žã次ã«18ïŒ18âã¢ã«
ããªãã³â11βïŒ18âãªãã·ãâååç©ïŒïŒã
éå ããå·¥çšãšç䟡ã§ãããšèããããã
ïŒïŒã¯æŽã«ãç°æ§äœã®ç°ç¶ããã¢ã»ã¿ãŒã«
ïŒïŒã®åœ¢ç¶ã§ååšãåŸããåŸã€ãŠãšã¹ãã©ãâ
18ïŒ11βâã©ã¯ãã³ïŒïŒãšååç©RXãšã®åå¿
ã¯ç°ç¶ããã¢ã»ã¿ãŒã«ïŒïŒãçµç±ããŠé²è¡ãåŸ
ãããã®ç°ç¶ããã¢ã»ã¿ãŒã«ïŒïŒåã³ãåŸã€ãŠ
11βâããããã·â18âã¢ã«ãã«â18âã±ãã³
ïŒïŒã¯äŸãã°ã·ãªã«ã²ã«ã®è£å©ã«ãã容æã«è±
æ°ŽãããŠ18ïŒ18âã¢ã«ããªãã³â11βïŒ18âãªã
ã·ãååç©ïŒïŒãçæãåŸãããã®ååç©ã11
βâããããã·â18âã¢ã«ãã«â18âã±ãã³ãšå
æ§ã®æ¹æ³ã§éå ã11βâããããã·â18âã¢ã«ã
ã«ååç©ïŒïŒã補é ãåŸããåŸã€ãŠ11βâãã
ããã·â18âã¢ã«ãã«â18âã±ãã³ïŒïŒã®éå
ã«ãã11βâããããã·â18âã¢ã«ãã«ååç©ã
補é ããå·¥çšã¯ã11βâããããã·â18âã¢ã«ã
ã«â18âã±ãã³ïŒïŒãè±æ°Žã次ã«18ïŒ18âã¢ã«
ããªãã³â11βïŒ18âãªãã·ãâååç©ïŒïŒã
éå ããå·¥çšãšç䟡ã§ãããšèããããã
æ¬çºææ¹æ³äžãã¹ããã€ãäžã«ååšããæ»æã
ãæããªããœâåã³ïŒåã¯ããããã·ã«åºã¯äžæ
çã«ä¿è·ãããã®ã奜ãŸããããªããœåºã¯äŸãã°
ã±ã¿ãŒã«ã®åœ¢ç¶ã§ãããããã·ã«åºã¯ãšãŒãã«ãŸ
ãã¯ãšã¹ãã«ã®åœ¢ç¶ã§ä¿è·ããããéåžžã¯ããã
ãã·ã«åºããšã¹ãã«ã®åœ¢ç¶ã§ä¿è·ããã®ã奜ãŸã
ãã
ãæããªããœâåã³ïŒåã¯ããããã·ã«åºã¯äžæ
çã«ä¿è·ãããã®ã奜ãŸããããªããœåºã¯äŸãã°
ã±ã¿ãŒã«ã®åœ¢ç¶ã§ãããããã·ã«åºã¯ãšãŒãã«ãŸ
ãã¯ãšã¹ãã«ã®åœ¢ç¶ã§ä¿è·ããããéåžžã¯ããã
ãã·ã«åºããšã¹ãã«ã®åœ¢ç¶ã§ä¿è·ããã®ã奜ãŸã
ãã
åŸã€ãŠäŸãã°åºçºç©è³ªã11βâããããã·âÎ
ïŒâãšã¹ãã¬ã³âïŒïŒ17âãžãªã³ã®å Žåãå ãã
ã®ãžãªã³ã11βâããããã·âÎïŒâãšã¹ãã¬ã³
âïŒïŒ17âãžãªã³ïŒïŒ17âãžãšãã¬ã³ã±ã¿ãŒã«ã«
転æãã次ã«ç¬¬ïŒåå¿å·¥çšã§éå°éã®æ¬¡äºæ²çŽ é ž
ã¢ã·ã«ã«ãããã®ãžãšãã¬ã³ã±ã¿ãŒã«ãïŒïŒ17â
ãžãªããœâÎïŒâãšã¹ãã¬ãâ18ïŒ11βâã©ã¯ã
ã³ïŒïŒ17âãžãšãã¬ã³ã±ã¿ãŒã«ã«è»¢æããã次ã«
äŸãã°èåã¡ãã«ãã°ãã·ãŠã ãŸãã¯ã¡ãã«ãªã
ãŠã ã«ãããã®ã©ã¯ãã³ã11βâããããã·â18
âã¡ãã«âÎïŒâãšã¹ãã¬ã³âïŒïŒ17ïŒ18âããª
ãªã³ïŒïŒ17âãžãšãã¬ã³ã±ã¿ãŒã«ã«è»¢æãã次ã«
åèšã±ã¿ãŒã«ããŠãªã«ãïŒãã·ãŠããŒæ³ã«ããé
å ããŠ11βâããããã·â18âã¡ãã«âÎïŒâãš
ã¹ãã¬ã³âïŒïŒ17âãžãªã³ïŒïŒ17âãžãšãã¬ã³ã±
ã¿ãŒã«ã補é ãããå æ°Žå解ã«ããä¿è·ã±ã¿ãŒã«
åºã®é€å»åã³åèšæ¹æ³ã«ãã11βâããããã·ã«
åºã®é€å»åŸ18âã¡ãã«âÎïŒâãšã¹ãã¬ã³âïŒïŒ
17âãžãªã³ãåŸããã次ã«äŸãã°ã«ãªãŠã ã¢ã»ã
ãªãã«ãããã®17âãªããœåºããšããã«åãããš
å ¬ç¥ã®ååç©ãã«ã²ã¹ãã¬ã«ïŒïŒ17αâãšããã«
â17βâããããã·â18âã¡ãã«âÎïŒâãšã¹ã
ã¬ã³âïŒâãªã³ïŒã補é ãããã
ïŒâãšã¹ãã¬ã³âïŒïŒ17âãžãªã³ã®å Žåãå ãã
ã®ãžãªã³ã11βâããããã·âÎïŒâãšã¹ãã¬ã³
âïŒïŒ17âãžãªã³ïŒïŒ17âãžãšãã¬ã³ã±ã¿ãŒã«ã«
転æãã次ã«ç¬¬ïŒåå¿å·¥çšã§éå°éã®æ¬¡äºæ²çŽ é ž
ã¢ã·ã«ã«ãããã®ãžãšãã¬ã³ã±ã¿ãŒã«ãïŒïŒ17â
ãžãªããœâÎïŒâãšã¹ãã¬ãâ18ïŒ11βâã©ã¯ã
ã³ïŒïŒ17âãžãšãã¬ã³ã±ã¿ãŒã«ã«è»¢æããã次ã«
äŸãã°èåã¡ãã«ãã°ãã·ãŠã ãŸãã¯ã¡ãã«ãªã
ãŠã ã«ãããã®ã©ã¯ãã³ã11βâããããã·â18
âã¡ãã«âÎïŒâãšã¹ãã¬ã³âïŒïŒ17ïŒ18âããª
ãªã³ïŒïŒ17âãžãšãã¬ã³ã±ã¿ãŒã«ã«è»¢æãã次ã«
åèšã±ã¿ãŒã«ããŠãªã«ãïŒãã·ãŠããŒæ³ã«ããé
å ããŠ11βâããããã·â18âã¡ãã«âÎïŒâãš
ã¹ãã¬ã³âïŒïŒ17âãžãªã³ïŒïŒ17âãžãšãã¬ã³ã±
ã¿ãŒã«ã補é ãããå æ°Žå解ã«ããä¿è·ã±ã¿ãŒã«
åºã®é€å»åã³åèšæ¹æ³ã«ãã11βâããããã·ã«
åºã®é€å»åŸ18âã¡ãã«âÎïŒâãšã¹ãã¬ã³âïŒïŒ
17âãžãªã³ãåŸããã次ã«äŸãã°ã«ãªãŠã ã¢ã»ã
ãªãã«ãããã®17âãªããœåºããšããã«åãããš
å ¬ç¥ã®ååç©ãã«ã²ã¹ãã¬ã«ïŒïŒ17αâãšããã«
â17βâããããã·â18âã¡ãã«âÎïŒâãšã¹ã
ã¬ã³âïŒâãªã³ïŒã補é ãããã
æ¬çºææ¹æ³ã§åŸãããäžéçæç©å³ã¡ãšã¹ãã©
ãâ18ïŒ11βâã©ã¯ãã³åã³ãšã¹ãã©ã³ç³»ã®11β
âããããã·â18âã¢ã«ãã«â18âã±ãã³ã¯æ°èŠ
ãªçæç©ã§ãããåŸã€ãŠæ¬çºæã¯æŽã«äžè¬åŒ ãåŒäžãR1åã³R2ã¯ååºãšå矩ãR5ã¯éé¢ã
ãšã¹ãã«åãŸãã¯ãšãŒãã«åããããã·ã«åºã
R6ã¯ã¢ã«ãã«ïŒççŽ ååïŒãïŒïŒããŸãã¯R5ãš
R6ãšãå ±ã«ãšããã·ã圢æããŠãããïŒïŒïŒâ
ãŸãã¯ïŒïŒïŒâäœã«ïŒåã®äºéçµåãååšããã
ã§ç€ºãããæ°èŠãªäžéçæç©ã«ä¿ãã
ãâ18ïŒ11βâã©ã¯ãã³åã³ãšã¹ãã©ã³ç³»ã®11β
âããããã·â18âã¢ã«ãã«â18âã±ãã³ã¯æ°èŠ
ãªçæç©ã§ãããåŸã€ãŠæ¬çºæã¯æŽã«äžè¬åŒ ãåŒäžãR1åã³R2ã¯ååºãšå矩ãR5ã¯éé¢ã
ãšã¹ãã«åãŸãã¯ãšãŒãã«åããããã·ã«åºã
R6ã¯ã¢ã«ãã«ïŒççŽ ååïŒãïŒïŒããŸãã¯R5ãš
R6ãšãå ±ã«ãšããã·ã圢æããŠãããïŒïŒïŒâ
ãŸãã¯ïŒïŒïŒâäœã«ïŒåã®äºéçµåãååšããã
ã§ç€ºãããæ°èŠãªäžéçæç©ã«ä¿ãã
ååšãåŸããšã¹ãã«åºã¯ççŽ ååïŒã18ã®ææ©
ã«ã«ãã³é žããèªå°ãããã18ïŒ11βâã©ã¯ãã³
åºãŸãã¯18âã¢ã«ãã«â18âãªããœåºã®å°å ¥åŸã«
åèšãšã¹ãã«åºãå°å ¥ãããã®ã奜ãŸãããååš
ãåŸããšãŒãã«åºã¯ãäŸãã°ãã¡ãã«ãšãŒãã«
âããšãã«ãšãŒãã«âãããã©ããããã©ãã«ãš
ãŒãã«âããŸãã¯ããªã¡ãã«ã·ãªã«ãšãŒãã«âåº
ã§ãã€ãŠããããååšãåŸãã±ã¿ãŒã«åºã¯ãäŸã
ã°ããšãã¬ã³ã±ã¿ãŒã«ãŸãã¯ãžã¡ãã«ã±ã¿ãŒã«åº
ã§ãã€ãŠãããã
ã«ã«ãã³é žããèªå°ãããã18ïŒ11βâã©ã¯ãã³
åºãŸãã¯18âã¢ã«ãã«â18âãªããœåºã®å°å ¥åŸã«
åèšãšã¹ãã«åºãå°å ¥ãããã®ã奜ãŸãããååš
ãåŸããšãŒãã«åºã¯ãäŸãã°ãã¡ãã«ãšãŒãã«
âããšãã«ãšãŒãã«âãããã©ããããã©ãã«ãš
ãŒãã«âããŸãã¯ããªã¡ãã«ã·ãªã«ãšãŒãã«âåº
ã§ãã€ãŠããããååšãåŸãã±ã¿ãŒã«åºã¯ãäŸã
ã°ããšãã¬ã³ã±ã¿ãŒã«ãŸãã¯ãžã¡ãã«ã±ã¿ãŒã«åº
ã§ãã€ãŠãããã
ãããã®æ°èŠãªäžéçæç©ã¯è¬çåŠçã«éèŠãª
18âã¢ã«ãã«âãšã¹ãã©ã³ååç©ã®è£œé çšã«éèŠ
ã§ããã®ã¿ã§ãªããæŽã«ãéèŠãªãšã¹ããã²ã³
æ§ãããã²ã¹ããã³æ§ã***å¶æ¢æ§åã³åšå²å粟
é»æ¢æ§ãæããã
18âã¢ã«ãã«âãšã¹ãã©ã³ååç©ã®è£œé çšã«éèŠ
ã§ããã®ã¿ã§ãªããæŽã«ãéèŠãªãšã¹ããã²ã³
æ§ãããã²ã¹ããã³æ§ã***å¶æ¢æ§åã³åšå²å粟
é»æ¢æ§ãæããã
æ¬çºæãäžèšã®å®æœäŸã«ã€ãæŽã«è©³çŽ°ã«èª¬æã
ãã
ãã
å®æœäŸ
10å
¥ãäžã€å£ãã©ã¹ã³ã«ãã·ã¯ããããµã³
4.2ãåé ¢é žé111.6ïœãçé žã«ã«ã·ãŠã 37.2ïœ
åã³æ²çŽ 22.8ïœãé æ¬¡æ³šå ¥ãããæ··åç©ã10åé
éæµããã沞隰åå¿æ··åç©ã«ã·ã¯ããããµã³600
mläžã®11βâããããã·âÎïŒâãšã¹ãã¬ã³â
ïŒïŒ17âãžãªã³ïŒïŒ17âãžãšãã¬ã³ã±ã¿ãŒã«22.8
ïœåã³ã¢ãŸã€ãœããããžãããªã«2.04ïœã®æžæ¿æ¶²
ãã§ããã ãè¿ éã«æ·»å ããã次ã«æ··åç©ã25å
ééæµããã次ã«åå¿æ··åç©ãå·åŽãæ²æ®¿ç©ã
éãããããªç¡«é žãããªãŠã 50ïœã溶解ãããŠã
ãæ°Ž2.5ãçšããŠæ¶²ãæŽæµã次ã«æ°Žã§æŽæµã
ãŠäžåãããç¡«é žãããªãŠã ã«ããææ©å±€ã也ç¥
ãããéãèžçºä¹Ÿç¥ããããåŸããã泡ç¶æ®æž£
ããã«ãšã³ïŒé ¢é žãšãã«1/1ãçšãã·ãªã«ã²ã«äž
ã§ã¯ãããã°ã©ãã«ããããé©åœãªåç»ã®çµæ¶å
ã«ããïŒïŒ17âãžãªããœâÎïŒâãšã¹ãã¬ãâ
18ïŒ11βâã©ã¯ãã³ïŒïŒ17âãžãšãã¬ã³ã±ã¿ãŒã«
13.6ïœãæ¶åºããïŒèç¹163ã164.5âïŒã
4.2ãåé ¢é žé111.6ïœãçé žã«ã«ã·ãŠã 37.2ïœ
åã³æ²çŽ 22.8ïœãé æ¬¡æ³šå ¥ãããæ··åç©ã10åé
éæµããã沞隰åå¿æ··åç©ã«ã·ã¯ããããµã³600
mläžã®11βâããããã·âÎïŒâãšã¹ãã¬ã³â
ïŒïŒ17âãžãªã³ïŒïŒ17âãžãšãã¬ã³ã±ã¿ãŒã«22.8
ïœåã³ã¢ãŸã€ãœããããžãããªã«2.04ïœã®æžæ¿æ¶²
ãã§ããã ãè¿ éã«æ·»å ããã次ã«æ··åç©ã25å
ééæµããã次ã«åå¿æ··åç©ãå·åŽãæ²æ®¿ç©ã
éãããããªç¡«é žãããªãŠã 50ïœã溶解ãããŠã
ãæ°Ž2.5ãçšããŠæ¶²ãæŽæµã次ã«æ°Žã§æŽæµã
ãŠäžåãããç¡«é žãããªãŠã ã«ããææ©å±€ã也ç¥
ãããéãèžçºä¹Ÿç¥ããããåŸããã泡ç¶æ®æž£
ããã«ãšã³ïŒé ¢é žãšãã«1/1ãçšãã·ãªã«ã²ã«äž
ã§ã¯ãããã°ã©ãã«ããããé©åœãªåç»ã®çµæ¶å
ã«ããïŒïŒ17âãžãªããœâÎïŒâãšã¹ãã¬ãâ
18ïŒ11βâã©ã¯ãã³ïŒïŒ17âãžãšãã¬ã³ã±ã¿ãŒã«
13.6ïœãæ¶åºããïŒèç¹163ã164.5âïŒã
åæ§ã®æ¹æ³ã§11βïŒ17βâãžããããã·âÎïŒ
âãšã¹ãã¬ã³âïŒâãªã³ ïŒâãšãã¬ã³ã±ã¿ãŒã«
åã³11βïŒ17βâãžããããã·â17αâã¡ãã«â
ÎïŒâãšã¹ãã¬ã³âïŒâãªã³ ïŒâãšãã¬ã³ã±ã¿
ãŒã« 17âé ¢é žå¡©ã察å¿ãã18ïŒ11βâã©ã¯ãã³
ã«è»¢æããã
âãšã¹ãã¬ã³âïŒâãªã³ ïŒâãšãã¬ã³ã±ã¿ãŒã«
åã³11βïŒ17βâãžããããã·â17αâã¡ãã«â
ÎïŒâãšã¹ãã¬ã³âïŒâãªã³ ïŒâãšãã¬ã³ã±ã¿
ãŒã« 17âé ¢é žå¡©ã察å¿ãã18ïŒ11βâã©ã¯ãã³
ã«è»¢æããã
å®æœäŸ
åé
¢é
žé11.16ïœãšçé
žã«ã«ã·ãŠã 3.7ïœãšãç¡
æ°Žã·ã¯ããããµã³420mläžã«æžæ¿ãããããã®æž
æ¿æ¶²ã«æ²çŽ 2.28ïœãæ·»å ããã
æ°Žã·ã¯ããããµã³420mläžã«æžæ¿ãããããã®æž
æ¿æ¶²ã«æ²çŽ 2.28ïœãæ·»å ããã
æ··åç©ã10åééæµåŸãç¡æ°Žã·ã¯ããããµã³40
mläžã®ÎïŒâãšã¹ãã¬ã³â11βïŒ17βâãžãªãŒã«
17βâé ¢é žå¡©1.9ïœåã³ã¢ãŸã€ãœããããžãããª
ã«0.2ïœã®æžæ¿æ¶²ãæ·»å ããåå¿æ··åç©ãæŽã«35
åééæµãããåå¿æ··åç©ã宀枩ãŸã§å·åŽããã€
ããã§éããã液ãããªç¡«é žãããªãŠã ïŒïŒ
溶液ã§æŽæµã次ã«æ°Žã§æŽæµãããç¡«é žãããªãŠã
ã§ä¹Ÿç¥ãããææ©å±€ãç空äžã§æ¿çž®ããŠæ²¹ç¶æ®æž£
3.7ïœãåŸãã
mläžã®ÎïŒâãšã¹ãã¬ã³â11βïŒ17βâãžãªãŒã«
17βâé ¢é žå¡©1.9ïœåã³ã¢ãŸã€ãœããããžãããª
ã«0.2ïœã®æžæ¿æ¶²ãæ·»å ããåå¿æ··åç©ãæŽã«35
åééæµãããåå¿æ··åç©ã宀枩ãŸã§å·åŽããã€
ããã§éããã液ãããªç¡«é žãããªãŠã ïŒïŒ
溶液ã§æŽæµã次ã«æ°Žã§æŽæµãããç¡«é žãããªãŠã
ã§ä¹Ÿç¥ãããææ©å±€ãç空äžã§æ¿çž®ããŠæ²¹ç¶æ®æž£
3.7ïœãåŸãã
ãã«ãšã³ïŒé
¢é
žãšãã«9/1ãçšãã·ãªã«ã²ã«äž
ã§ã¯ãããã°ã©ãã«ããã次ã«é©åœãªåç»ãçµæ¶
åãã17βâããããã·âÎïŒâãšã¹ãã¬ãâ
18ïŒ11βâã©ã¯ãã³17βâé ¢é žå¡©0.95ïœãåŸã
ïŒèç¹ïŒ157ã159âïŒã
ã§ã¯ãããã°ã©ãã«ããã次ã«é©åœãªåç»ãçµæ¶
åãã17βâããããã·âÎïŒâãšã¹ãã¬ãâ
18ïŒ11βâã©ã¯ãã³17βâé ¢é žå¡©0.95ïœãåŸã
ïŒèç¹ïŒ157ã159âïŒã
åæ§ã®æ¹æ³ã§ÎïŒâãšã¹ãã¬ã³â11βïŒ17βâ
ãžãªãŒã«17βâé ¢é žå¡©ã11βâããããã·âÎïŒ
âãšã¹ãã¬ã³â17âãªã³17âãšãã¬ã³ã±ã¿ãŒã«å
ã³17αâãšãã«âÎïŒâãšã¹ãã¬ã³â11βïŒ17β
âãžãªãŒã«17βâé ¢é žå¡©ã察å¿ãã18ïŒ11βâã©
ã¯ãã³ã«è»¢æããã
ãžãªãŒã«17βâé ¢é žå¡©ã11βâããããã·âÎïŒ
âãšã¹ãã¬ã³â17âãªã³17âãšãã¬ã³ã±ã¿ãŒã«å
ã³17αâãšãã«âÎïŒâãšã¹ãã¬ã³â11βïŒ17β
âãžãªãŒã«17βâé ¢é žå¡©ã察å¿ãã18ïŒ11βâã©
ã¯ãã³ã«è»¢æããã
å®æœäŸ
ãã°ãã·ãŠã å±3.8ïœããšãŒãã«280mläžã«æžæ¿
ãããããã°ãã·ãŠã ãå®å šã«æº¶è§£ãããŸã§èå
ã¡ãã«ãæ·»å ããã宀枩ãŸã§å·åŽãç¡æ°Žãã«ãšã³
420mläžã®ïŒïŒ17âãžãªããœâÎïŒâãšã¹ãã¬ã
â18ïŒ11βâã©ã¯ãã³ïŒïŒ17âãžãšãã¬ã³ã±ã¿ãŒ
ã«22.2ïœã®æº¶æ¶²ãæ·»å ãããåå¿æ··åç©ã宀枩ã§
ïŒæéæ¹æãã次ã«0.4Nã®å¡©é ž400mlã§æ éã«å
解ããæ°Ž2.8äžã«æ³šå ¥ãããã¡ãã¬ã³ã¯ããªã
ã§æœåºããŠåŸãããææ©å±€ãæ°Žã§æŽæµããŠäžå
ããç¡«é žãããªãŠã ã§ä¹Ÿç¥ããéããŠç空äžã§
èžçºä¹Ÿç¥ããããèç¹175ã178âã®11βâããã
ãã·â18âã¡ãã«âÎïŒâãšã¹ãã¬ã³âïŒïŒ17ïŒ
18âããªãªã³ïŒïŒ17âãžãšãã¬ã³ã±ã¿ãŒã«19.5ïœ
ãåŸãã
ãããããã°ãã·ãŠã ãå®å šã«æº¶è§£ãããŸã§èå
ã¡ãã«ãæ·»å ããã宀枩ãŸã§å·åŽãç¡æ°Žãã«ãšã³
420mläžã®ïŒïŒ17âãžãªããœâÎïŒâãšã¹ãã¬ã
â18ïŒ11βâã©ã¯ãã³ïŒïŒ17âãžãšãã¬ã³ã±ã¿ãŒ
ã«22.2ïœã®æº¶æ¶²ãæ·»å ãããåå¿æ··åç©ã宀枩ã§
ïŒæéæ¹æãã次ã«0.4Nã®å¡©é ž400mlã§æ éã«å
解ããæ°Ž2.8äžã«æ³šå ¥ãããã¡ãã¬ã³ã¯ããªã
ã§æœåºããŠåŸãããææ©å±€ãæ°Žã§æŽæµããŠäžå
ããç¡«é žãããªãŠã ã§ä¹Ÿç¥ããéããŠç空äžã§
èžçºä¹Ÿç¥ããããèç¹175ã178âã®11βâããã
ãã·â18âã¡ãã«âÎïŒâãšã¹ãã¬ã³âïŒïŒ17ïŒ
18âããªãªã³ïŒïŒ17âãžãšãã¬ã³ã±ã¿ãŒã«19.5ïœ
ãåŸãã
åæ§ã®æ¹æ³ã§ãå®æœäŸïŒã§åŸããã18ïŒ11
βâã©ã¯ãã³ã察å¿ãã11βâããããã·â18â
ã¡ãã«â18âã±ãã³ã«è»¢æããã
βâã©ã¯ãã³ã察å¿ãã11βâããããã·â18â
ã¡ãã«â18âã±ãã³ã«è»¢æããã
èåã¡ãã«ãã°ãã·ãŠã ã«ä»£ããŠèåãšãã«ã
ã°ãã·ãŠã ã䜿çšãããšå¯Ÿå¿ããïŒâãšãã«â18
âã±ãã³ãåŸããããããã«ãªããŠã ã䜿çšãã
ãšå¯Ÿå¿ãã18âããã«â18âã±ãã³ãåŸãããã
ã°ãã·ãŠã ã䜿çšãããšå¯Ÿå¿ããïŒâãšãã«â18
âã±ãã³ãåŸããããããã«ãªããŠã ã䜿çšãã
ãšå¯Ÿå¿ãã18âããã«â18âã±ãã³ãåŸãããã
å®æœäŸ
ïœ æªåŠçã®ïŒïŒ17âãžãªããœâÎïŒâãšã¹ãã¬
ãâ18ïŒ11βâã©ã¯ãã³ïŒïŒ17âãžãšãã¬ã³ã±
ã¿ãŒã«7.5ïœãã¡ã¿ããŒã«50mlã«æº¶è§£ãããã
ãã®æº¶æ¶²ã«æ°Žé žåãããªãŠã 10ïŒ æº¶æ¶²20mlãæ·»
å ã次ã«æ··åç©ã50âã§1.5æéæ¹æããã次
ã«æ··åç©ãæ°Ž750mläžã«æ³šå ¥ããã2Nå¡©é žã«ã
ãäžåãPHïŒã«ãããé ¢é žãšãã«ã«ããæœåº
ããæœåºç©ãç¡«é žãããªãŠã ã§ä¹Ÿç¥ãããé
ããŠèžçºä¹Ÿç¥ããããš11βâããããã·âïŒïŒ
17âãžãªããœâÎïŒâãšã¹ãã¬ã³â13âã«ã«ã
ã³é žïŒïŒ17âãžãšãã¬ã³ã±ã¿ãŒã«4.2ïœãåŸã
ããã
ãâ18ïŒ11βâã©ã¯ãã³ïŒïŒ17âãžãšãã¬ã³ã±
ã¿ãŒã«7.5ïœãã¡ã¿ããŒã«50mlã«æº¶è§£ãããã
ãã®æº¶æ¶²ã«æ°Žé žåãããªãŠã 10ïŒ æº¶æ¶²20mlãæ·»
å ã次ã«æ··åç©ã50âã§1.5æéæ¹æããã次
ã«æ··åç©ãæ°Ž750mläžã«æ³šå ¥ããã2Nå¡©é žã«ã
ãäžåãPHïŒã«ãããé ¢é žãšãã«ã«ããæœåº
ããæœåºç©ãç¡«é žãããªãŠã ã§ä¹Ÿç¥ãããé
ããŠèžçºä¹Ÿç¥ããããš11βâããããã·âïŒïŒ
17âãžãªããœâÎïŒâãšã¹ãã¬ã³â13âã«ã«ã
ã³é žïŒïŒ17âãžãšãã¬ã³ã±ã¿ãŒã«4.2ïœãåŸã
ããã
ïœ 11βâããããã·âïŒïŒ17âãžãªããœâÎïŒ
âãšã¹ãã¬ã³â13âã«ã«ãã³é žïŒïŒ17âãžãšã
ã¬ã³ã±ã¿ãŒã«1.21ïœãããã©ããããã©ã³20ml
äžã«æº¶è§£ããããïŒâãŸã§å·åŽããïŒâã®æº¶æ¶²
ã«1.5Mã®ã¡ãã«ãªããŠã ïŒmlãåŸã ã«æ·»å
ãã次ã«æº¶æ¶²ãïŒâã§äžæéæ¹æãããæ°·æ°Ž
200mläžã«æ³šå ¥ããã¡ãã¬ã³ã¯ããªãã§æœåº
ããæœåºç©ãç¡«é žãããªãŠã ã§ä¹Ÿç¥ãããé
ããŠç空äžã§èžçºãããŠæ®æž£ãåŸããæ®æž£ã
ïŒãã«ãšã³ïŒé ¢é žãšãã«1/1ïŒãçšããŠã·ãªã«äž
ã§ã¯ãããã°ã©ãã«ãããèç¹175ã178âã®11
βâããããã·â18âã¡ãã«âÎïŒâãšã¹ãã¬
ã³âïŒïŒ17ïŒ18âããªãªã³ïŒïŒ17âãžãšãã¬ã³
ã±ã¿ãŒã«0.48ïœãåŸãã
âãšã¹ãã¬ã³â13âã«ã«ãã³é žïŒïŒ17âãžãšã
ã¬ã³ã±ã¿ãŒã«1.21ïœãããã©ããããã©ã³20ml
äžã«æº¶è§£ããããïŒâãŸã§å·åŽããïŒâã®æº¶æ¶²
ã«1.5Mã®ã¡ãã«ãªããŠã ïŒmlãåŸã ã«æ·»å
ãã次ã«æº¶æ¶²ãïŒâã§äžæéæ¹æãããæ°·æ°Ž
200mläžã«æ³šå ¥ããã¡ãã¬ã³ã¯ããªãã§æœåº
ããæœåºç©ãç¡«é žãããªãŠã ã§ä¹Ÿç¥ãããé
ããŠç空äžã§èžçºãããŠæ®æž£ãåŸããæ®æž£ã
ïŒãã«ãšã³ïŒé ¢é žãšãã«1/1ïŒãçšããŠã·ãªã«äž
ã§ã¯ãããã°ã©ãã«ãããèç¹175ã178âã®11
βâããããã·â18âã¡ãã«âÎïŒâãšã¹ãã¬
ã³âïŒïŒ17ïŒ18âããªãªã³ïŒïŒ17âãžãšãã¬ã³
ã±ã¿ãŒã«0.48ïœãåŸãã
å®æœäŸ
11βâããããã·â18âã¡ãã«âÎïŒâãšã¹ã
ã¬ã³âïŒïŒ17ïŒ18âããªãªã³ïŒïŒ17âãžãšãã¬ã³
ã±ã¿ãŒã«10.2ïœã100ïŒ ãšã¿ããŒã«97mlã«æžæ¿ã
ãã次ã«ãžãšãã¬ã³ã°ãªã³ãŒã«233mlãããã©ãž
ã³æ°Žåç©97mlåã³ããã©ãžã³âäºå¡©åºé žå¡©20.4ïœ
ãæ·»å ããã
ã¬ã³âïŒïŒ17ïŒ18âããªãªã³ïŒïŒ17âãžãšãã¬ã³
ã±ã¿ãŒã«10.2ïœã100ïŒ ãšã¿ããŒã«97mlã«æžæ¿ã
ãã次ã«ãžãšãã¬ã³ã°ãªã³ãŒã«233mlãããã©ãž
ã³æ°Žåç©97mlåã³ããã©ãžã³âäºå¡©åºé žå¡©20.4ïœ
ãæ·»å ããã
åå¿æ··åç©ã100âã§ïŒæéé眮ã次ã«ç²æ«æ°Ž
é žåã«ãªãŠã 37ïœåã³ãžãšãã¬ã³ã°ãªã³ãŒã«713
mlãæ·»å ããã
é žåã«ãªãŠã 37ïœåã³ãžãšãã¬ã³ã°ãªã³ãŒã«713
mlãæ·»å ããã
次ã«åå¿æ··åç©ã180âãŸã§å ç±ãã€ã€äœæ²žç¹
åç»ãèžçé€å»ããæ··åç©ã180âã§4.5æéé眮
ããã次ã«æ··åç©ã宀枩ãŸã§å·åŽãæ°·æ°ŽïŒäžã«
æ³šå ¥ããã18ïŒ HClãçšããŠæ··åç©ãäžåããã
éã«ããçµæ¶ãååºãæ°Žã§æŽæµãç空äžã§70â
ã§ä¹Ÿç¥ãããé ¢é žãšãã«ããçµæ¶ãåæ¶åºããã
åç»ãèžçé€å»ããæ··åç©ã180âã§4.5æéé眮
ããã次ã«æ··åç©ã宀枩ãŸã§å·åŽãæ°·æ°ŽïŒäžã«
æ³šå ¥ããã18ïŒ HClãçšããŠæ··åç©ãäžåããã
éã«ããçµæ¶ãååºãæ°Žã§æŽæµãç空äžã§70â
ã§ä¹Ÿç¥ãããé ¢é žãšãã«ããçµæ¶ãåæ¶åºããã
ãã®æ¹æ³ã«ããèç¹176ã179âã®11βâããã
ãã·â18âã¡ãã«âÎïŒâãšã¹ãã¬ã³âïŒïŒ17â
ãžãªã³ïŒïŒ17âãžãšãã¬ã³ã±ã¿ãŒã«8.45ïœãåŸ
ãã
ãã·â18âã¡ãã«âÎïŒâãšã¹ãã¬ã³âïŒïŒ17â
ãžãªã³ïŒïŒ17âãžãšãã¬ã³ã±ã¿ãŒã«8.45ïœãåŸ
ãã
åæ§ã«ããŠå®æœäŸã«èšèŒã®å¥ã®11βâããã
ãã·â18âã¢ã«ãã«â18âã±ãã³ãéå ã察å¿ã
ã11βâããããã·â18âã¢ã«ãã«ååç©ãåŸ
ãã
ãã·â18âã¢ã«ãã«â18âã±ãã³ãéå ã察å¿ã
ã11βâããããã·â18âã¢ã«ãã«ååç©ãåŸ
ãã
å®æœäŸ
ïœ 11βâããããã·â18âã¡ãã«âÎïŒâãšã¹
ãã¬ã³âïŒïŒ17ïŒ18âããªãªã³ïŒïŒ17âãžãšã
ã¬ã³ã±ã¿ãŒã«6.7ïœããã«ãšã³ïŒé ¢é žãšãã«1/1
220mläžã«æº¶è§£ããã次ã«æº¶æ¶²ã«ã·ãªã«ã²ã«67
ïœãæ·»å ããã宀枩ã§16æéæ¹æåŸãã·ãªã«ã²
ã«ãéé€å»ããã«ãšã³ïŒé ¢é žãšãã«ã§ååã«
æŽæµããã液ãèžçºä¹Ÿç¥ãã11βïŒ18âãšã
ãã·â18ïŒ18âã¡ãã¬ã³âÎïŒâãšã¹ãã¬ã³â
ïŒïŒ17âãžãªã³ïŒïŒ17âãžãšãã¬ã³ã±ã¿ãŒã«
6.1ïœãåŸããïŒèç¹152ã155âïŒã
ãã¬ã³âïŒïŒ17ïŒ18âããªãªã³ïŒïŒ17âãžãšã
ã¬ã³ã±ã¿ãŒã«6.7ïœããã«ãšã³ïŒé ¢é žãšãã«1/1
220mläžã«æº¶è§£ããã次ã«æº¶æ¶²ã«ã·ãªã«ã²ã«67
ïœãæ·»å ããã宀枩ã§16æéæ¹æåŸãã·ãªã«ã²
ã«ãéé€å»ããã«ãšã³ïŒé ¢é žãšãã«ã§ååã«
æŽæµããã液ãèžçºä¹Ÿç¥ãã11βïŒ18âãšã
ãã·â18ïŒ18âã¡ãã¬ã³âÎïŒâãšã¹ãã¬ã³â
ïŒïŒ17âãžãªã³ïŒïŒ17âãžãšãã¬ã³ã±ã¿ãŒã«
6.1ïœãåŸããïŒèç¹152ã155âïŒã
ïœ 11βïŒ18âãšããã·â18ïŒ18âã¡ãã¬ã³âÎ
ïŒâãšã¹ãã¬ã³âïŒïŒ17âãžãªã³ïŒïŒ17âãžãš
ãã¬ã³ã±ã¿ãŒã«3.15ïœã100ïŒ ãšã¿ããŒã«30ml
ã«æžæ¿ããããæžæ¿æ¶²ã«ãžãšãã¬ã³ã°ãªã³ãŒã«
72mlãããã©ãžã³æ°Žåç©29mlåã³ããã©ãžã³â
ãžãããâã¯ããªã6.3ïœãæ·»å ãããåå¿æ··
åç©ã100âã§ïŒæéé眮ãã次ã«ç²æ«æ°Žé žå
ã«ãªãŠã 11.4ïœåã³ãžãšãã¬ã³ã°ãªã³ãŒã«220
mlãæ·»å ãããåå¿æ··åç©ã200âãŸã§å ç±ã
ã€ã€äœæ²žç¹åç»ãèžçé€å»ãã200âã§1.5æé
é眮ãããåå¿æ··åç©ã宀枩ãŸã§å·åŽãæ°ŽïŒ
äžã«æ³šå ¥ãããæ··åç©ã18ïŒ å¡©é žã§äžåãïŒæ
éæ¹æã次ã«çµæ¶ãéé€å»ããæ°Žã§æŽæµãç
空äžã§70âã§ä¹Ÿç¥ãããé ¢é žãšãã«ããåçµæ¶
ããèç¹177ã179.5âã®11βâããããã·â18
âã¡ãã«âÎïŒâãšã¹ãã¬ã³âïŒïŒ17âãžãªã³
ïŒïŒ17âãžãšãã¬ã³ã±ã¿ãŒã«1.1ïœãåŸãã
ïŒâãšã¹ãã¬ã³âïŒïŒ17âãžãªã³ïŒïŒ17âãžãš
ãã¬ã³ã±ã¿ãŒã«3.15ïœã100ïŒ ãšã¿ããŒã«30ml
ã«æžæ¿ããããæžæ¿æ¶²ã«ãžãšãã¬ã³ã°ãªã³ãŒã«
72mlãããã©ãžã³æ°Žåç©29mlåã³ããã©ãžã³â
ãžãããâã¯ããªã6.3ïœãæ·»å ãããåå¿æ··
åç©ã100âã§ïŒæéé眮ãã次ã«ç²æ«æ°Žé žå
ã«ãªãŠã 11.4ïœåã³ãžãšãã¬ã³ã°ãªã³ãŒã«220
mlãæ·»å ãããåå¿æ··åç©ã200âãŸã§å ç±ã
ã€ã€äœæ²žç¹åç»ãèžçé€å»ãã200âã§1.5æé
é眮ãããåå¿æ··åç©ã宀枩ãŸã§å·åŽãæ°ŽïŒ
äžã«æ³šå ¥ãããæ··åç©ã18ïŒ å¡©é žã§äžåãïŒæ
éæ¹æã次ã«çµæ¶ãéé€å»ããæ°Žã§æŽæµãç
空äžã§70âã§ä¹Ÿç¥ãããé ¢é žãšãã«ããåçµæ¶
ããèç¹177ã179.5âã®11βâããããã·â18
âã¡ãã«âÎïŒâãšã¹ãã¬ã³âïŒïŒ17âãžãªã³
ïŒïŒ17âãžãšãã¬ã³ã±ã¿ãŒã«1.1ïœãåŸãã
å®æœäŸ
ã·ã¯ããããµã³356mläžã®åé
¢é
žé9.54ïœåã³
çé žã«ã«ã·ãŠã 3.18ïœã®æžæ¿æ¶²ã«æ²çŽ 1.95ïœãæ·»
å ãããæ··åç©ã10åééæµããã沞隰混åç©ã«
ã·ã¯ããããµã³100mläžã®11βâããããã·âãš
ã¹ãã©ã³âïŒïŒ17âãžãªã³ïŒïŒ17âãžãšãã¬ã³ã±
ã¿ãŒã«1.95ïœåã³ã¢ãŸã€ãœããããžãããªã«
0.174ïœã®æžæ¿æ¶²ãæ·»å ãã次ã«åå¿æ··åç©ã30
åééæµããã
çé žã«ã«ã·ãŠã 3.18ïœã®æžæ¿æ¶²ã«æ²çŽ 1.95ïœãæ·»
å ãããæ··åç©ã10åééæµããã沞隰混åç©ã«
ã·ã¯ããããµã³100mläžã®11βâããããã·âãš
ã¹ãã©ã³âïŒïŒ17âãžãªã³ïŒïŒ17âãžãšãã¬ã³ã±
ã¿ãŒã«1.95ïœåã³ã¢ãŸã€ãœããããžãããªã«
0.174ïœã®æžæ¿æ¶²ãæ·»å ãã次ã«åå¿æ··åç©ã30
åééæµããã
åå¿æ··åç©ã宀枩ãŸã§å·åŽããã€ããäžã§é
ããã液ãããªç¡«é žãããªãŠã ïŒïŒ 氎溶液ã§æŽ
æµã次ã«æ°Žã§æŽæµãããç¡«é žãããªãŠã ã§ææ©çž
ã也ç¥ããç空äžã§èžçºããã也ç¥æ®æž£3.7ïœã
åŸãããã«ãšã³ïŒé ¢é žãšãã«6/4ãçšããŠã·ãªã«
ã²ã«äžã§ã¯ãããã°ã©ãã«ããïŒïŒ17âãžãªããœ
âãšã¹ãã©ãâ18ïŒ11βâã©ã¯ãã³ïŒïŒ17âãžãš
ãã¬ã³ã±ã¿ãŒã«ãåŸãã
ããã液ãããªç¡«é žãããªãŠã ïŒïŒ 氎溶液ã§æŽ
æµã次ã«æ°Žã§æŽæµãããç¡«é žãããªãŠã ã§ææ©çž
ã也ç¥ããç空äžã§èžçºããã也ç¥æ®æž£3.7ïœã
åŸãããã«ãšã³ïŒé ¢é žãšãã«6/4ãçšããŠã·ãªã«
ã²ã«äžã§ã¯ãããã°ã©ãã«ããïŒïŒ17âãžãªããœ
âãšã¹ãã©ãâ18ïŒ11βâã©ã¯ãã³ïŒïŒ17âãžãš
ãã¬ã³ã±ã¿ãŒã«ãåŸãã
æ¬çºæã®å®æœæ
æ§ã®ããã€ãã®äŸãäžèšã«èŠçŽ
ããã
ããã
(1) åºçºç©è³ªãã11βâããããã·â13âã¡ãã«
âãŽãã³ååç©ããåŒ ãåŒäžãR1ã¯H2ïŒïŒšïŒOR3ïŒïŒïŒ¯ãŸãã¯ã±ã¿
ãŒã«åãR2ã¯ïŒ¯ïŒã±ã¿ãŒã«åïŒïŒšïŒOR4ïŒ
ãŸãã¯ïŒÎ±âã¢ã«ãã«ïŒïŒÎ²OR4ïŒïœã¢ã«ãã«åº
ã¯ççŽ ååïŒãïŒãR3åã³R4ã¯ïŒšãŸãã¯ã¢ã·
ã«ãããã¯ã¢ã«ãã«ã®ãããªä¿è·åºã§ããïœã§
ããïŒïŒïŒâãŸãã¯ïŒïŒïŒâäœã«äžåã®äºéçµ
åãååšããŠãããã§ç€ºãããç¹èš±è«æ±ã®ç¯å²
ïŒãŸãã¯ïŒã«èšèŒã®æ¹æ³ã
âãŽãã³ååç©ããåŒ ãåŒäžãR1ã¯H2ïŒïŒšïŒOR3ïŒïŒïŒ¯ãŸãã¯ã±ã¿
ãŒã«åãR2ã¯ïŒ¯ïŒã±ã¿ãŒã«åïŒïŒšïŒOR4ïŒ
ãŸãã¯ïŒÎ±âã¢ã«ãã«ïŒïŒÎ²OR4ïŒïœã¢ã«ãã«åº
ã¯ççŽ ååïŒãïŒãR3åã³R4ã¯ïŒšãŸãã¯ã¢ã·
ã«ãããã¯ã¢ã«ãã«ã®ãããªä¿è·åºã§ããïœã§
ããïŒïŒïŒâãŸãã¯ïŒïŒïŒâäœã«äžåã®äºéçµ
åãååšããŠãããã§ç€ºãããç¹èš±è«æ±ã®ç¯å²
ïŒãŸãã¯ïŒã«èšèŒã®æ¹æ³ã
(2) åŒäžãR1ãH2ïŒïŒšïŒïŒ¯ã¢ã»ãã«ïŒãŸãã¯ãš
ãã¬ã³ãžãªãã·ãR2ããšãã¬ã³ãžãªãã·ãα
ïŒÎ²ïŒ¯ã¢ã»ãã«ïŒãŸãã¯ïŒÎ±âã¢ã«ãã«ïŒâ
4CïŒïŒÎ²ïŒ¯ã¢ã»ãã«ïŒã§ããïŒïŒïŒâãŸãã¯
ïŒïŒïŒâäœã«ïŒåã®äºéçµåãååšããåé (1)
ã«èšèŒã®æ¹æ³ã
ãã¬ã³ãžãªãã·ãR2ããšãã¬ã³ãžãªãã·ãα
ïŒÎ²ïŒ¯ã¢ã»ãã«ïŒãŸãã¯ïŒÎ±âã¢ã«ãã«ïŒâ
4CïŒïŒÎ²ïŒ¯ã¢ã»ãã«ïŒã§ããïŒïŒïŒâãŸãã¯
ïŒïŒïŒâäœã«ïŒåã®äºéçµåãååšããåé (1)
ã«èšèŒã®æ¹æ³ã
(3) 次äºæ²çŽ é
žã¢ã·ã«ãæ²çŽ åã³ééå±ã®ã¢ã·ã«
åç©ãããã®å Žã§åœ¢æãããç¹èš±è«æ±ã®ç¯å²ïŒ
ãïŒããã³åé (1)ã(2)ã®ããããã«èšèŒã®æ¹
æ³ã
åç©ãããã®å Žã§åœ¢æãããç¹èš±è«æ±ã®ç¯å²ïŒ
ãïŒããã³åé (1)ã(2)ã®ããããã«èšèŒã®æ¹
æ³ã
(4) ééå±ã®ã¢ã·ã«åç©ãšããŠåé
¢é
žéã䜿çšã
ãåé (3)ã«èšèŒã®æ¹æ³ã
ãåé (3)ã«èšèŒã®æ¹æ³ã
(5) ã¹ããã€ãïŒã°ã©ã ã¢ã«ã«ã€ãæ²çŽ 1.5ã3.0
ã°ã©ã ã¢ã«ã䜿çšãæŽã«å°ããšãåœéã®åã¢ã·
ã«åéã䜿çšããåé (3)ãŸãã¯(4)ã«èšèŒã®æ¹
æ³ã
ã°ã©ã ã¢ã«ã䜿çšãæŽã«å°ããšãåœéã®åã¢ã·
ã«åéã䜿çšããåé (3)ãŸãã¯(4)ã«èšèŒã®æ¹
æ³ã
(6) æ²çŽ ïŒã°ã©ã ã¢ã«ã«ã€ãåã¢ã·ã«åé1.5ã
ïŒã°ã©ã ã¢ã«ã䜿çšããåé (5)ã«èšèŒã®æ¹æ³ã
ïŒã°ã©ã ã¢ã«ã䜿çšããåé (5)ã«èšèŒã®æ¹æ³ã
(7) 第ïŒæ®µéã§ç°ç¶çåæ°ŽçŽ ã溶åªãšããŠäœ¿çšã
ãç¹èš±è«æ±ã®ç¯å²ïŒãïŒåã³åèš(1)ã(6)ã«èšèŒ
ã®æ¹æ³ã
ãç¹èš±è«æ±ã®ç¯å²ïŒãïŒåã³åèš(1)ã(6)ã«èšèŒ
ã®æ¹æ³ã
(8) 溶åªãšããŠã·ã¯ããããµã³ã䜿çšããåé
(7)
ã«èšèŒã®æ¹æ³ã
ã«èšèŒã®æ¹æ³ã
(9) 第ïŒæ®µéã§ãã©ãžã«ã«éå§å€ã®ååšäžã§åå¿
ãçèµ·ããããšãç¹åŸŽãšããç¹èš±è«æ±ã®ç¯å²ïŒ
ãïŒåã³åé (1)ã(8)ã«èšèŒã®æ¹æ³ã
ãçèµ·ããããšãç¹åŸŽãšããç¹èš±è«æ±ã®ç¯å²ïŒ
ãïŒåã³åé (1)ã(8)ã«èšèŒã®æ¹æ³ã
(10) ã©ãžã«ã«éå§å€ãšããŠã¢ãŸã€ãœããããžãã
ãªã«ã䜿çšããåé (9)ã«èšèŒã®æ¹æ³ã
ãªã«ã䜿çšããåé (9)ã«èšèŒã®æ¹æ³ã
(11) ã¹ããã€ãïŒã°ã©ã ã¢ã«ã«ã€ãã©ãžã«ã«éå§
å€0.1ã0.25ã°ã©ã ã¢ã«ã䜿çšããåé (9)ãŸã
ã¯(10)ã«èšèŒã®æ¹æ³ã
å€0.1ã0.25ã°ã©ã ã¢ã«ã䜿çšããåé (9)ãŸã
ã¯(10)ã«èšèŒã®æ¹æ³ã
(12) ååç©RXãŸãã¯ã¢ã«ãã«ãªããŠã ååç©äž
ã®ã¢ã«ãã«åºãççŽ ååïŒãïŒãæããç¹èš±è«
æ±ã®ç¯å²ïŒïŒïŒåã³åé (1)ã(11)ã«èšèŒã®æ¹æ³ã
ã®ã¢ã«ãã«åºãççŽ ååïŒãïŒãæããç¹èš±è«
æ±ã®ç¯å²ïŒïŒïŒåã³åé (1)ã(11)ã«èšèŒã®æ¹æ³ã
(13) ãšã¹ãã©ãâ18ïŒ11βâã©ã¯ãã³ãšååç©
RXãšã®åå¿ãç¡æ°Žç¶æ ã®äžæŽ»æ§æº¶åªäžã§çèµ·
ããç¹èš±è«æ±ã®ç¯å²ïŒåã³åé (1)ã(12)ã«èšèŒã®
æ¹æ³ã
RXãšã®åå¿ãç¡æ°Žç¶æ ã®äžæŽ»æ§æº¶åªäžã§çèµ·
ããç¹èš±è«æ±ã®ç¯å²ïŒåã³åé (1)ã(12)ã«èšèŒã®
æ¹æ³ã
(14) ã¢ã«ãã«ãªããŠã ååç©ãš11βâãããã
ã·â13âã«ã«ãã³é žãšã®åå¿ãäœæž©ãã€ç¡æ°Žç¶
æ ã®äžæŽ»æ§æº¶åªäžã§çèµ·ããç¹èš±è«æ±ã®ç¯å²ïŒ
åã³åé (1)ã(12)ã«èšèŒã®æ¹æ³ã
ã·â13âã«ã«ãã³é žãšã®åå¿ãäœæž©ãã€ç¡æ°Žç¶
æ ã®äžæŽ»æ§æº¶åªäžã§çèµ·ããç¹èš±è«æ±ã®ç¯å²ïŒ
åã³åé (1)ã(12)ã«èšèŒã®æ¹æ³ã
(15) 11βâããããã·â18âã¢ã«ãã«â18âã±
ãã³ã®18âãªããœåºã®éå ãã18âã±ãã³ãã
ã®ããã©ãŸã³ãŸãã¯ã»ãã«ã«ããŸã³ã«è»¢æãã
ã®ããã©ãŸã³ãŸãã¯ã»ãã«ã«ããŸã³ãã¢ã«ã«ãª
æ§ç¶æ ã§å解ããããšã«ãããçèµ·ãããç¹èš±
è«æ±ã®ç¯å²ïŒåã³åé (1)ã(14)ã«èšèŒã®æ¹æ³ã
ãã³ã®18âãªããœåºã®éå ãã18âã±ãã³ãã
ã®ããã©ãŸã³ãŸãã¯ã»ãã«ã«ããŸã³ã«è»¢æãã
ã®ããã©ãŸã³ãŸãã¯ã»ãã«ã«ããŸã³ãã¢ã«ã«ãª
æ§ç¶æ ã§å解ããããšã«ãããçèµ·ãããç¹èš±
è«æ±ã®ç¯å²ïŒåã³åé (1)ã(14)ã«èšèŒã®æ¹æ³ã
(16) 沞隰ãžãšãã¬ã³ã°ãªã³ãŒã«äžã§éå
ãçèµ·
ãããããã«ããåå¿äžã«åœ¢æãããæ°Žãèžç
é€å»ãããåé (15)ã«èšèŒã®æ¹æ³ã
ãããããã«ããåå¿äžã«åœ¢æãããæ°Žãèžç
é€å»ãããåé (15)ã«èšèŒã®æ¹æ³ã
(17) ååç©ãäžè¬åŒ
ãåŒäžãR1åã³R2ã¯åé
(1)ãšå矩ãR5ã¯é
é¢ããšã¹ãã«åãŸãã¯ãšãŒãã«åããããã·ã«
åºãR6ã¯ççŽ ååïŒãïŒã®ã¢ã«ãã«ãŸãã¯R5
ãšR6ãšãå ±ã«ãšããã·ã圢æããŠãããïŒïŒ
ïŒâãŸãã¯ïŒïŒïŒâäœã«äžåã®äºéçµåãååš
ãããã§ç€ºãããååç©ãã補é ãããããšã
ç¹åŸŽãšãããšã¹ãã©ã³ç³»ã®æ°èŠãªã¹ããã€ãã®
補æ³ã
é¢ããšã¹ãã«åãŸãã¯ãšãŒãã«åããããã·ã«
åºãR6ã¯ççŽ ååïŒãïŒã®ã¢ã«ãã«ãŸãã¯R5
ãšR6ãšãå ±ã«ãšããã·ã圢æããŠãããïŒïŒ
ïŒâãŸãã¯ïŒïŒïŒâäœã«äžåã®äºéçµåãååš
ãããã§ç€ºãããååç©ãã補é ãããããšã
ç¹åŸŽãšãããšã¹ãã©ã³ç³»ã®æ°èŠãªã¹ããã€ãã®
補æ³ã
(18) åŒ
ãåŒäžãR1åã³R2ã¯åé
(1)ãšå矩ãR5ã¯é
é¢ããšã¹ãã«åãŸãã¯ãšãŒãã«åããããã·ã«
åºãR6ã¯ççŽ ååïŒãïŒã®ã¢ã«ãã«ãŸãã¯R5
ãšR6ãšãå ±ã«ãšããã·ã圢æããŠãããïŒïŒ
ïŒâãŸãã¯ïŒïŒïŒâäœã«ïŒåã®äºéçµåãååš
ããŠãããã§ç€ºãããååç©ã
é¢ããšã¹ãã«åãŸãã¯ãšãŒãã«åããããã·ã«
åºãR6ã¯ççŽ ååïŒãïŒã®ã¢ã«ãã«ãŸãã¯R5
ãšR6ãšãå ±ã«ãšããã·ã圢æããŠãããïŒïŒ
ïŒâãŸãã¯ïŒïŒïŒâäœã«ïŒåã®äºéçµåãååš
ããŠãããã§ç€ºãããååç©ã
(19) R1ãH2ãŸãã¯ãšãã¬ã³ãžãªãã·ãR2ããšã
ã¬ã³ãžãªãã·ãŸãã¯Î±ïŒšïŒÎ²ïŒ¯ã¢ã»ãã«ïŒãR5
ãOHãR6ãã¡ãã«ããŸãã¯R5ãšR6ãšãå ±ã«ãš
ããã·ã圢æããŠãããïŒïŒïŒâãŸãã¯ïŒïŒïŒ
âäœã«ïŒåã®äºéçµåãååšããããšãç¹åŸŽãš
ããåé (18)ã«èšèŒã®ååç©ã
ã¬ã³ãžãªãã·ãŸãã¯Î±ïŒšïŒÎ²ïŒ¯ã¢ã»ãã«ïŒãR5
ãOHãR6ãã¡ãã«ããŸãã¯R5ãšR6ãšãå ±ã«ãš
ããã·ã圢æããŠãããïŒïŒïŒâãŸãã¯ïŒïŒïŒ
âäœã«ïŒåã®äºéçµåãååšããããšãç¹åŸŽãš
ããåé (18)ã«èšèŒã®ååç©ã
Claims (1)
- ãç¹èš±è«æ±ã®ç¯å²ã ïŒ 11βâããããã·â13âã¡ãã«âãŽãã³åå
ç©ãéå°éã®æ¬¡äºæ²çŽ é žã¢ã·ã«ãšåå¿ããããã
ã«ããçæãããšã¹ãã©ãâ18ïŒ11βâã©ã¯ãã³
ãååç©RXïŒïŒ²ã¯ã¢ã«ãã«ãã¯MgBrãããã¯
LiïŒãšåå¿ãããçæããã11βâããããã·â
18âã¢ã«ãã«â18âã±ãã³ã次ã«éå ããŠãšã¹ã
ã©ã³ç³»ã®11βâããããã·â18âã¢ã«ãã«ã¹ãã
ã€ãã補é ããããšãç¹åŸŽãšãããšã¹ãã©ã³ç³»ã®
11βâããããã·â18âã¢ã«ãã«ã¹ããã€ãã®è£œ
æ³ã ïŒ 11βâããããã·â13âã¡ãã«âãŽãã³åå
ç©ãéå°éã®æ¬¡äºæ²çŽ é žã¢ã·ã«ãšåå¿ããããã
ã«ããçæãããšã¹ãã©ãâ18ïŒ11βâã©ã¯ãã³
ãå ãå æ°Žå解ããŠ11βâããããã·â13âã«ã«
ãã³é žååç©ãçæãåèšã«ã«ãã³é žååç©ãã¢
ã«ãã«ãªããŠã ååç©ãšåå¿ãããçæããã11
βâããããã·â18âã¢ã«ãã«â18âã±ãã³ã次
ã«éå ããŠãšã¹ãã©ã³ç³»ã®11βâããããã·â18
âã¢ã«ãã«ã¹ããã€ãã補é ããããšãç¹åŸŽãšã
ããšã¹ãã©ã³ç³»ã®11βâããããã·â18âã¢ã«ã
ã«ã¹ããã€ãã®è£œæ³ã
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NLAANVRAGE7411607,A NL188647C (nl) | 1952-03-29 | 1974-09-02 | Werkwijze voor het bereiden van 11beta-hydroxy-18-alkylestraanverbindingen. |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5148647A JPS5148647A (en) | 1976-04-26 |
JPS6211000B2 true JPS6211000B2 (ja) | 1987-03-10 |
Family
ID=19822010
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP50104464A Granted JPS5148647A (en) | 1974-09-02 | 1975-08-27 | 11 beeta hidorokishi 188 arukiruuesutorankagobutsunoseiho |
Country Status (12)
Country | Link |
---|---|
US (1) | US4031074A (ja) |
JP (1) | JPS5148647A (ja) |
CA (1) | CA1069117A (ja) |
CH (1) | CH616944A5 (ja) |
DD (1) | DD124880A5 (ja) |
DE (1) | DE2538862C2 (ja) |
DK (1) | DK138499B (ja) |
FR (1) | FR2283150A1 (ja) |
GB (1) | GB1519826A (ja) |
HU (1) | HU173555B (ja) |
SE (1) | SE415021B (ja) |
SU (1) | SU826957A3 (ja) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU572589B2 (en) | 1983-12-14 | 1988-05-12 | Upjohn Company, The | 11(alpha)-difluoromethyl and (e)-and (z)-11-fluoromethylene steroids |
JP2006507369A (ja) * | 2002-08-16 | 2006-03-02 | ãã¡ã«ãã·ã¢ã»ã¢ã³ãã»ã¢ãããžã§ã³ã»ã«ã³ãããŒã»ãšã«ãšã«ã·ãŒ | ïŒâã¢ã³ããã¹ãã³âïŒÎ²âãªãŒã«ã¹ããã€ãäžéäœããã³ãããã®è£œæ³ |
US20070066579A1 (en) * | 2002-08-16 | 2007-03-22 | White Michael J | 5-androsten-3beta-ol steroid intermediates and processs for their preparation |
EP2825547B1 (en) | 2012-03-15 | 2019-07-24 | Merck Sharp & Dohme B.V. | Combined synthesis route for etonogestrel and desogestrel |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3780026A (en) * | 1969-01-13 | 1973-12-18 | Shionogi & Co | Biochemical aldosterone synthesis |
-
1975
- 1975-07-18 US US05/597,271 patent/US4031074A/en not_active Expired - Lifetime
- 1975-07-29 GB GB31661/75A patent/GB1519826A/en not_active Expired
- 1975-08-07 CA CA233,054A patent/CA1069117A/en not_active Expired
- 1975-08-12 CH CH1047575A patent/CH616944A5/de unknown
- 1975-08-22 DK DK379775AA patent/DK138499B/da not_active IP Right Cessation
- 1975-08-27 JP JP50104464A patent/JPS5148647A/ja active Granted
- 1975-08-29 HU HU75AO422A patent/HU173555B/hu not_active IP Right Cessation
- 1975-08-29 DD DD188093A patent/DD124880A5/xx unknown
- 1975-09-01 SU SU752170509A patent/SU826957A3/ru active
- 1975-09-01 DE DE2538862A patent/DE2538862C2/de not_active Expired
- 1975-09-01 SE SE7509674A patent/SE415021B/xx not_active IP Right Cessation
- 1975-09-02 FR FR7526925A patent/FR2283150A1/fr active Granted
Also Published As
Publication number | Publication date |
---|---|
DK138499B (da) | 1978-09-18 |
SU826957A3 (ru) | 1981-04-30 |
SE7509674L (sv) | 1976-03-03 |
CH616944A5 (ja) | 1980-04-30 |
FR2283150B1 (ja) | 1979-09-14 |
DK138499C (ja) | 1979-02-26 |
HU173555B (hu) | 1979-06-28 |
DK379775A (ja) | 1976-03-03 |
FR2283150A1 (fr) | 1976-03-26 |
GB1519826A (en) | 1978-08-02 |
CA1069117A (en) | 1980-01-01 |
DE2538862A1 (de) | 1976-03-11 |
US4031074A (en) | 1977-06-21 |
DE2538862C2 (de) | 1984-08-02 |
DD124880A5 (ja) | 1977-03-16 |
JPS5148647A (en) | 1976-04-26 |
SE415021B (sv) | 1980-09-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JPS5933600B2 (ja) | æ°èŠãªïŒïŒïŒïŒïŒâã¢ã«ããªãã³ã¹ããã€ãã®è£œé æ¹æ³ | |
US4292251A (en) | 11β-Substituted steroids | |
US3166577A (en) | 1, 2-dimethyl estrogens and intermediates used in the production thereof | |
SU671733A3 (ru) | СпПÑПб пПлÑÑеМО пÑПОзвПЎМÑÑ 15-ÑÑеÑПОЎПв | |
US3357973A (en) | 7alpha-mono-and dihalomethyl steroids | |
US3262949A (en) | 7-methyl androstane compounds | |
US5093502A (en) | 14α,17α-dihydroxy-17β-substituted steroids | |
FR2569408A1 (fr) | Nouveaux steroides substitues en position 10 par un radical comportant une double ou triple liaison, leur procede de preparation, leur application comme medicaments, les compositions pharmaceutiques les renfermant | |
JPS6211000B2 (ja) | ||
US3377365A (en) | (optionally 17-alkylated) 11beta, 13beta-dialkylgona-1, 3, 5(10)-triene-3, 17beta-diols, ethers and esters thereof | |
US4016269A (en) | 17α-HYDROXY-1,3,5(10),15-ESTRATETRAENES AND PROCESS FOR THEIR PRODUCTION | |
US3972906A (en) | Novel - 11-substituted steroids of the estrane series | |
JPH027959B2 (ja) | ||
US3365445A (en) | 1beta, 2beta-methylene steroids of the androstane series | |
JPS6044317B2 (ja) | ïŒïŒÎ²âããããã·âïŒïŒâã¢ã«ãã«âãšã¹ãã©ã³ååç©ã®è£œæ³ | |
US3080399A (en) | Cyclopentanophenanthrene compounds and process | |
US3082223A (en) | 2-methylene-androstanes | |
US3998813A (en) | Process for the preparation of 11β-hydroxy-18-alkyl-estrane compounds | |
US3082225A (en) | Novel 1-methyl-1, 3, 5(10), 9(11)-estratetraenes and methods for their manufacture | |
US3086033A (en) | 1-methyl-17-alkyl-11-oxygenated delta1, 3, 5 (10)-estrogenic compounds | |
US3159620A (en) | Process for the preparation of 17 alpha-ethynyl-19-norandrostene compounds | |
US3045030A (en) | Fluorinated androstanes and intermediates relating thereto | |
US3179660A (en) | 13beta-n-propyl-18-nor-cortisone derivative and process of preparation | |
US3642839A (en) | 19-homo-steroids | |
US3324152A (en) | 1alpha-methyl-delta2-androstenes |