JPH0225895B2 - - Google Patents
Info
- Publication number
- JPH0225895B2 JPH0225895B2 JP20171685A JP20171685A JPH0225895B2 JP H0225895 B2 JPH0225895 B2 JP H0225895B2 JP 20171685 A JP20171685 A JP 20171685A JP 20171685 A JP20171685 A JP 20171685A JP H0225895 B2 JPH0225895 B2 JP H0225895B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- octane
- methylene
- trisubstituted
- methylenebicyclo
- 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
- -1 2,6,7-trisubstituted-3-methylenebicyclo[3.3.0]octanes Chemical class 0.000 claims description 84
- 150000001875 compounds Chemical class 0.000 claims description 84
- 229930195733 hydrocarbon Natural products 0.000 claims description 40
- 239000004215 Carbon black (E152) Substances 0.000 claims description 38
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000005916 2-methylpentyl group Chemical group 0.000 claims description 3
- 125000006267 biphenyl group Chemical group 0.000 claims description 3
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- WFYDTEDUNIVDKQ-UHFFFAOYSA-N 5-methylidene-2,3,3a,4,6,6a-hexahydro-1h-pentalene Chemical compound C1CCC2CC(=C)CC21 WFYDTEDUNIVDKQ-UHFFFAOYSA-N 0.000 claims 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- HIGZCTKLVJZSQN-UHFFFAOYSA-N 6-methylidene-2,3,3a,4,5,6a-hexahydro-1h-pentalene Chemical compound C1CCC2C(=C)CCC21 HIGZCTKLVJZSQN-UHFFFAOYSA-N 0.000 claims 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 77
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 33
- 238000000034 method Methods 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 22
- 239000007788 liquid Substances 0.000 description 21
- 239000000126 substance Substances 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 14
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 13
- 150000002430 hydrocarbons Chemical class 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000000543 intermediate Substances 0.000 description 10
- 239000007800 oxidant agent Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 238000004440 column chromatography Methods 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- AEBWATHAIVJLTA-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydropentalene Chemical group C1CCC2CCCC21 AEBWATHAIVJLTA-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- GOPLUNUWFWQAEF-OMHHLVHNSA-N (3as,4s,5r,6as)-5-[tert-butyl(dimethyl)silyl]oxy-4-[(e,3s)-3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]-2-methylidene-3,3a,4,5,6,6a-hexahydro-1h-pentalen-1-ol Chemical compound OC1C(=C)C[C@@H]2[C@H](/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)CCCCC)[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H]21 GOPLUNUWFWQAEF-OMHHLVHNSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 230000003595 spectral effect Effects 0.000 description 6
- 150000001342 alkaline earth metals Chemical class 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000005694 sulfonylation reaction Methods 0.000 description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
- FGTJJHCZWOVVNH-UHFFFAOYSA-N tert-butyl-[tert-butyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)O[Si](C)(C)C(C)(C)C FGTJJHCZWOVVNH-UHFFFAOYSA-N 0.000 description 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003146 anticoagulant agent Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010511 deprotection reaction Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 3
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 230000006103 sulfonylation Effects 0.000 description 3
- MBKTYSZQKVRNJC-QYGNAZJJSA-N (3as,4s,5r,6as)-4-[(1e)-4-cyclohexyl-4-hydroxyhexa-1,5-dienyl]-5-hydroxy-2-methylidene-3,3a,4,5,6,6a-hexahydropentalen-1-one Chemical compound C(/[C@H]1[C@H]2[C@@H](C(C(=C)C2)=O)C[C@H]1O)=C\CC(O)(C=C)C1CCCCC1 MBKTYSZQKVRNJC-QYGNAZJJSA-N 0.000 description 2
- APENTFVJVLMZNV-OZAXNUMCSA-N (3as,4s,5r,6as)-4-[(1e)-4-cyclopentyl-4-hydroxyhexa-1,5-dienyl]-5-hydroxy-2-methylidene-3,3a,4,5,6,6a-hexahydropentalen-1-one Chemical compound C(/[C@H]1[C@H]2[C@@H](C(C(=C)C2)=O)C[C@H]1O)=C\CC(O)(C=C)C1CCCC1 APENTFVJVLMZNV-OZAXNUMCSA-N 0.000 description 2
- XYVHPXLZPCRXIU-OZAXNUMCSA-N (3as,4s,5r,6as)-4-[(e)-4-cyclohexyl-4-hydroxypent-1-enyl]-5-hydroxy-2-methylidene-3,3a,4,5,6,6a-hexahydropentalen-1-one Chemical compound C(\[C@H]1[C@H]2[C@@H](C(C(=C)C2)=O)C[C@H]1O)=C/CC(O)(C)C1CCCCC1 XYVHPXLZPCRXIU-OZAXNUMCSA-N 0.000 description 2
- LDVPUMLIOINRMJ-RKDXZGSFSA-N (3as,4s,5r,6as)-4-[(e)-4-cyclopentyl-4-hydroxypent-1-enyl]-5-hydroxy-2-methylidene-3,3a,4,5,6,6a-hexahydropentalen-1-one Chemical compound C(\[C@H]1[C@H]2[C@@H](C(C(=C)C2)=O)C[C@H]1O)=C/CC(O)(C)C1CCCC1 LDVPUMLIOINRMJ-RKDXZGSFSA-N 0.000 description 2
- AWOPQUZJLOHSSA-LKPYAXCDSA-N (3as,4s,5r,6as)-4-[(e)-4-ethenyl-4-hydroxyoct-1-enyl]-5-hydroxy-2-methylidene-3,3a,4,5,6,6a-hexahydropentalen-1-one Chemical compound C1C(=C)C(=O)[C@@H]2[C@@H]1[C@H](/C=C/CC(O)(CCCC)C=C)[C@H](O)C2 AWOPQUZJLOHSSA-LKPYAXCDSA-N 0.000 description 2
- SMFCTRVQVXTHHB-MEGVTPSMSA-N (3as,4s,5r,6as)-4-[(e)-5-ethoxy-3-hydroxy-3-methylpent-1-enyl]-5-hydroxy-2-methylidene-3,3a,4,5,6,6a-hexahydropentalen-1-one Chemical compound C1C(=C)C(=O)[C@@H]2[C@@H]1[C@H](/C=C/C(C)(O)CCOCC)[C@H](O)C2 SMFCTRVQVXTHHB-MEGVTPSMSA-N 0.000 description 2
- ZRHAXNLUJXQACR-MEGVTPSMSA-N (3as,4s,5r,6as)-4-[(e)-5-ethoxy-4-hydroxy-4-methylpent-1-enyl]-5-hydroxy-2-methylidene-3,3a,4,5,6,6a-hexahydropentalen-1-one Chemical compound C1C(=C)C(=O)[C@@H]2[C@@H]1[C@H](/C=C/CC(C)(O)COCC)[C@H](O)C2 ZRHAXNLUJXQACR-MEGVTPSMSA-N 0.000 description 2
- GTJQYSPOGQAZBH-PYPWCOPSSA-N (3as,4s,5r,6as)-4-[(e)-5-ethoxy-4-hydroxypent-1-enyl]-5-hydroxy-2-methylidene-3,3a,4,5,6,6a-hexahydropentalen-1-one Chemical compound C1C(=C)C(=O)[C@@H]2[C@@H]1[C@H](/C=C/CC(O)COCC)[C@H](O)C2 GTJQYSPOGQAZBH-PYPWCOPSSA-N 0.000 description 2
- BPEKLPYSUIQZSX-SPNXZMCRSA-N (3as,4s,5r,6as)-4-[(e,3s)-3-cyclohexyl-3-hydroxyprop-1-enyl]-5-hydroxy-2-methylidene-3,3a,4,5,6,6a-hexahydropentalen-1-one Chemical compound C1([C@@H](\C=C\[C@H]2[C@H]3[C@@H](C(C(=C)C3)=O)C[C@H]2O)O)CCCCC1 BPEKLPYSUIQZSX-SPNXZMCRSA-N 0.000 description 2
- CQHQIFFJOROEDH-HJIJAPLXSA-N (3as,4s,5r,6as)-5-hydroxy-4-[(1e)-4-hydroxy-4-(phenoxymethyl)hexa-1,5-dienyl]-2-methylidene-3,3a,4,5,6,6a-hexahydropentalen-1-one Chemical compound C(/[C@H]1[C@H]2[C@@H](C(C(=C)C2)=O)C[C@H]1O)=C\CC(O)(C=C)COC1=CC=CC=C1 CQHQIFFJOROEDH-HJIJAPLXSA-N 0.000 description 2
- XNBVFKULNODUGM-RBOIFPPRSA-N (3as,4s,5r,6as)-5-hydroxy-4-[(1e,3s)-3-hydroxy-7-methylocta-1,6-dienyl]-2-methylidene-3,3a,4,5,6,6a-hexahydropentalen-1-one Chemical compound C1C(=C)C(=O)[C@@H]2[C@@H]1[C@H](/C=C/[C@@H](O)CCC=C(C)C)[C@H](O)C2 XNBVFKULNODUGM-RBOIFPPRSA-N 0.000 description 2
- RHQGRERSDDKVMP-NQQUCPGWSA-N (3as,4s,5r,6as)-5-hydroxy-4-[(1e,3s)-3-hydroxy-9-methyldeca-1,8-dienyl]-2-methylidene-3,3a,4,5,6,6a-hexahydropentalen-1-one Chemical compound C1C(=C)C(=O)[C@@H]2[C@@H]1[C@H](/C=C/[C@@H](O)CCCCC=C(C)C)[C@H](O)C2 RHQGRERSDDKVMP-NQQUCPGWSA-N 0.000 description 2
- ASCAAPPNWHIVJA-ZPAPNVOBSA-N (3as,4s,5r,6as)-5-hydroxy-4-[(e)-3-hydroxy-3-methyloct-1-enyl]-2-methylidene-3,3a,4,5,6,6a-hexahydropentalen-1-one Chemical compound C1C(=C)C(=O)[C@@H]2[C@@H]1[C@H](/C=C/C(C)(O)CCCCC)[C@H](O)C2 ASCAAPPNWHIVJA-ZPAPNVOBSA-N 0.000 description 2
- KZQAWLLQWNZRKW-GZDDHCOCSA-N (3as,4s,5r,6as)-5-hydroxy-4-[(e)-4-hydroxy-4-methyloct-1-enyl]-2-methylidene-3,3a,4,5,6,6a-hexahydropentalen-1-one Chemical compound C1C(=C)C(=O)[C@@H]2[C@@H]1[C@H](/C=C/CC(C)(O)CCCC)[C@H](O)C2 KZQAWLLQWNZRKW-GZDDHCOCSA-N 0.000 description 2
- HNMXQYRKLPMUMQ-XCLYIWHWSA-N (3as,4s,5r,6as)-5-hydroxy-4-[(e)-4-hydroxynon-1-enyl]-2-methylidene-3,3a,4,5,6,6a-hexahydropentalen-1-one Chemical compound C1C(=C)C(=O)[C@@H]2[C@@H]1[C@H](/C=C/CC(O)CCCCC)[C@H](O)C2 HNMXQYRKLPMUMQ-XCLYIWHWSA-N 0.000 description 2
- WQYNYOWCQAATSJ-SQLYMHTPSA-N (3as,4s,5r,6as)-5-hydroxy-4-[(e,3s)-3-hydroxy-5-methylnon-1-enyl]-2-methylidene-3,3a,4,5,6,6a-hexahydropentalen-1-one Chemical compound C1C(=C)C(=O)[C@@H]2[C@@H]1[C@H](/C=C/[C@@H](O)CC(C)CCCC)[C@H](O)C2 WQYNYOWCQAATSJ-SQLYMHTPSA-N 0.000 description 2
- FJYUPHDTSWMKSS-GQJHTITNSA-N (3as,4s,5r,6as)-5-hydroxy-4-[(e,3s)-3-hydroxydec-1-enyl]-2-methylidene-3,3a,4,5,6,6a-hexahydropentalen-1-one Chemical compound C1C(=C)C(=O)[C@@H]2[C@@H]1[C@H](/C=C/[C@@H](O)CCCCCCC)[C@H](O)C2 FJYUPHDTSWMKSS-GQJHTITNSA-N 0.000 description 2
- VHFVHLGPVIHHJW-PDXVQUJRSA-N (3as,4s,5r,6as)-5-hydroxy-4-[(e,3s)-3-hydroxyoct-1-enyl]-2-methylidene-3,3a,4,5,6,6a-hexahydropentalen-1-one Chemical compound C1C(=C)C(=O)[C@@H]2[C@@H]1[C@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C2 VHFVHLGPVIHHJW-PDXVQUJRSA-N 0.000 description 2
- FSJSYDFBTIVUFD-SUKNRPLKSA-N (z)-4-hydroxypent-3-en-2-one;oxovanadium Chemical compound [V]=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FSJSYDFBTIVUFD-SUKNRPLKSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IFIURUKVHSUUEC-UHFFFAOYSA-N 2,3,4,5,6,6a-hexahydro-1H-pentalen-3a-yloxysilane Chemical compound [SiH3]OC12CCCC2CCC1 IFIURUKVHSUUEC-UHFFFAOYSA-N 0.000 description 2
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
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- 125000005650 substituted phenylene group Chemical group 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20171685A JPS6261937A (ja) | 1985-09-13 | 1985-09-13 | ２，６，７−三置換−３−メチレンビシクロ〔３．３．０〕オクタン類およびその製造法 |
| US06/905,976 US5283349A (en) | 1985-09-13 | 1986-09-11 | 2,6,7-trisubstituted-3-methylenebicyclo(3.3.0)-octanes, and process for production thereof |
| DE91100972T DE3689338T2 (de) | 1985-09-13 | 1986-09-12 | Isocarbacyclinderivate. |
| EP86307060A EP0216585B1 (en) | 1985-09-13 | 1986-09-12 | 2,6,7-Trisubstituted-3-methylenebicyclo [3.3.0]octanes and process for production thereof |
| EP91100972A EP0427708B1 (en) | 1985-09-13 | 1986-09-12 | Isocarbacyclin derivatives |
| DE8686307060T DE3682735D1 (de) | 1985-09-13 | 1986-09-12 | 2,6,7-trisubstituierte-3-methylenbicyclo(3.3.0)octane und verfahren zu ihrer herstellung. |
| US07/764,068 US5206416A (en) | 1985-09-13 | 1991-09-24 | Isocarbacyclin derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20171685A JPS6261937A (ja) | 1985-09-13 | 1985-09-13 | ２，６，７−三置換−３−メチレンビシクロ〔３．３．０〕オクタン類およびその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6261937A JPS6261937A (ja) | 1987-03-18 |
| JPH0225895B2 true JPH0225895B2 (nl) | 1990-06-06 |
Family
ID=16445744
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20171685A Granted JPS6261937A (ja) | 1985-09-13 | 1985-09-13 | ２，６，７−三置換−３−メチレンビシクロ〔３．３．０〕オクタン類およびその製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6261937A (nl) |
-
1985
- 1985-09-13 JP JP20171685A patent/JPS6261937A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6261937A (ja) | 1987-03-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |