CN1884297A - 合成16-脱氢孕甾双烯酮醇醋酸酯及其同类物的方法 - Google Patents
合成16-脱氢孕甾双烯酮醇醋酸酯及其同类物的方法 Download PDFInfo
- Publication number
- CN1884297A CN1884297A CN 200510011966 CN200510011966A CN1884297A CN 1884297 A CN1884297 A CN 1884297A CN 200510011966 CN200510011966 CN 200510011966 CN 200510011966 A CN200510011966 A CN 200510011966A CN 1884297 A CN1884297 A CN 1884297A
- Authority
- CN
- China
- Prior art keywords
- steroid
- acetate
- dehydrogenation
- diketene
- false
- 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.)
- Granted
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 title claims abstract description 54
- 238000000034 method Methods 0.000 title claims abstract description 33
- 239000000039 congener Substances 0.000 title description 5
- 230000002194 synthesizing effect Effects 0.000 title 1
- 150000003431 steroids Chemical class 0.000 claims abstract description 79
- WQLVFSAGQJTQCK-UHFFFAOYSA-N diosgenin Natural products CC1C(C2(CCC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 WQLVFSAGQJTQCK-UHFFFAOYSA-N 0.000 claims abstract description 52
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 41
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 28
- NWMIYTWHUDFRPL-UHFFFAOYSA-N sapogenin Natural products COC(=O)C1(CO)C(O)CCC2(C)C1CCC3(C)C2CC=C4C5C(C)(O)C(C)CCC5(CCC34C)C(=O)O NWMIYTWHUDFRPL-UHFFFAOYSA-N 0.000 claims abstract description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000001301 oxygen Substances 0.000 claims abstract description 17
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 17
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 230000001590 oxidative effect Effects 0.000 claims abstract description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 64
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 42
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims description 40
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 33
- DWCSNWXARWMZTG-UHFFFAOYSA-N Trigonegenin A Natural products CC1C(C2(CCC3C4(C)CCC(O)C=C4CCC3C2C2)C)C2OC11CCC(C)CO1 DWCSNWXARWMZTG-UHFFFAOYSA-N 0.000 claims description 32
- WQLVFSAGQJTQCK-VKROHFNGSA-N diosgenin Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)CC4=CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 WQLVFSAGQJTQCK-VKROHFNGSA-N 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 235000019439 ethyl acetate Nutrition 0.000 claims description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- 238000005286 illumination Methods 0.000 claims description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 230000001235 sensitizing effect Effects 0.000 claims description 15
- 235000008754 Agave americana Nutrition 0.000 claims description 14
- 240000004246 Agave americana Species 0.000 claims description 14
- OXLGJTRVVNGJRK-UHFFFAOYSA-N Hecogenin Natural products CC1CCC2(CC3CC4C5CCC6CC(O)CCC6(C)C5CC(=O)C4(C)C3C2C)OC1 OXLGJTRVVNGJRK-UHFFFAOYSA-N 0.000 claims description 14
- QOLRLLFJMZLYQJ-KYRQEAISSA-N Sisalagenin Chemical compound O([C@@H]1[C@@H]([C@]2(C(=O)C[C@@H]3[C@@]4(C)CC[C@H](O)C[C@@H]4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@H](C)CO1 QOLRLLFJMZLYQJ-KYRQEAISSA-N 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 14
- 230000003647 oxidation Effects 0.000 claims description 13
- 238000007539 photo-oxidation reaction Methods 0.000 claims description 13
- 238000010992 reflux Methods 0.000 claims description 13
- KFKRXESVMDBTNQ-UHFFFAOYSA-N 3-[18-(2-carboxylatoethyl)-8,13-bis(1-hydroxyethyl)-3,7,12,17-tetramethyl-22,23-dihydroporphyrin-21,24-diium-2-yl]propanoate Chemical compound N1C2=C(C)C(C(C)O)=C1C=C(N1)C(C)=C(C(O)C)C1=CC(C(C)=C1CCC(O)=O)=NC1=CC(C(CCC(O)=O)=C1C)=NC1=C2 KFKRXESVMDBTNQ-UHFFFAOYSA-N 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 9
- 238000004440 column chromatography Methods 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 5
- 238000001953 recrystallisation Methods 0.000 claims description 5
- YNHJECZULSZAQK-UHFFFAOYSA-N tetraphenylporphyrin Chemical compound C1=CC(C(=C2C=CC(N2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3N2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 YNHJECZULSZAQK-UHFFFAOYSA-N 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 4
- 229960000907 methylthioninium chloride Drugs 0.000 claims description 4
- 238000007664 blowing Methods 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- RBTBFTRPCNLSDE-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazin-5-ium Chemical compound C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 RBTBFTRPCNLSDE-UHFFFAOYSA-N 0.000 claims 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 abstract description 10
- 238000005516 engineering process Methods 0.000 abstract description 8
- 239000003814 drug Substances 0.000 abstract description 6
- 239000003054 catalyst Substances 0.000 abstract description 5
- 238000005336 cracking Methods 0.000 abstract description 5
- 238000003912 environmental pollution Methods 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 4
- 238000011161 development Methods 0.000 abstract description 3
- 229940079593 drug Drugs 0.000 abstract description 3
- 238000000746 purification Methods 0.000 abstract description 3
- 238000003379 elimination reaction Methods 0.000 abstract description 2
- 238000009776 industrial production Methods 0.000 abstract description 2
- 239000007800 oxidant agent Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- INLFWQCRAJUDCR-IQVMEADQSA-N (1R,2S,4S,5'S,6R,7S,8R,9S,12S,13S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane] Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CCCCC4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@H](C)CO1 INLFWQCRAJUDCR-IQVMEADQSA-N 0.000 abstract 1
- YLFRRPUBVUAHSR-RRPFGEQOSA-N 16,17-didehydropregnenolone Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC=C(C(=O)C)[C@@]1(C)CC2 YLFRRPUBVUAHSR-RRPFGEQOSA-N 0.000 abstract 1
- YLFRRPUBVUAHSR-UHFFFAOYSA-N 16-dehydro-pregnenolone Natural products C1C=C2CC(O)CCC2(C)C2C1C1CC=C(C(=O)C)C1(C)CC2 YLFRRPUBVUAHSR-UHFFFAOYSA-N 0.000 abstract 1
- 230000009286 beneficial effect Effects 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
- 239000012141 concentrate Substances 0.000 description 9
- 230000006837 decompression Effects 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 9
- 239000012362 glacial acetic acid Substances 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 9
- 229910052753 mercury Inorganic materials 0.000 description 9
- 238000010525 oxidative degradation reaction Methods 0.000 description 9
- 239000005297 pyrex Substances 0.000 description 9
- 230000003595 spectral effect Effects 0.000 description 9
- 238000006731 degradation reaction Methods 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 7
- 230000015556 catabolic process Effects 0.000 description 7
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 6
- 239000005314 uranium glass Substances 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910000474 mercury oxide Inorganic materials 0.000 description 3
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical class [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000012286 potassium permanganate Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- -1 pregnene keto-alcohol compound Chemical class 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910004373 HOAc Inorganic materials 0.000 description 2
- 229940117975 chromium trioxide Drugs 0.000 description 2
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 239000003550 marker Substances 0.000 description 2
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 2
- 239000003504 photosensitizing agent Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 231100000489 sensitizer Toxicity 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- ZNOKGRXACCSDPY-UHFFFAOYSA-N tungsten trioxide Chemical compound O=[W](=O)=O ZNOKGRXACCSDPY-UHFFFAOYSA-N 0.000 description 2
- MFWFDRBPQDXFRC-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;vanadium Chemical compound [V].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O MFWFDRBPQDXFRC-LNTINUHCSA-N 0.000 description 1
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 1
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- BIOPPFDHKHWJIA-UHFFFAOYSA-N anthracene-9,10-dinitrile Chemical compound C1=CC=C2C(C#N)=C(C=CC=C3)C3=C(C#N)C2=C1 BIOPPFDHKHWJIA-UHFFFAOYSA-N 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000010504 bond cleavage reaction Methods 0.000 description 1
- 238000007233 catalytic pyrolysis Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229960004544 cortisone Drugs 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011964 heteropoly acid Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 150000005856 steroid saponins Chemical class 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Steroid Compounds (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2005100119666A CN100469786C (zh) | 2005-06-20 | 2005-06-20 | 合成16-脱氢孕甾双烯酮醇醋酸酯或同类物的方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2005100119666A CN100469786C (zh) | 2005-06-20 | 2005-06-20 | 合成16-脱氢孕甾双烯酮醇醋酸酯或同类物的方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1884297A true CN1884297A (zh) | 2006-12-27 |
CN100469786C CN100469786C (zh) | 2009-03-18 |
Family
ID=37582613
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB2005100119666A Expired - Fee Related CN100469786C (zh) | 2005-06-20 | 2005-06-20 | 合成16-脱氢孕甾双烯酮醇醋酸酯或同类物的方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN100469786C (zh) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101974057A (zh) * | 2010-10-13 | 2011-02-16 | 天津大学 | 醋酸妊娠双烯醇酮及其同类物的绿色制备方法 |
CN102153611A (zh) * | 2011-02-18 | 2011-08-17 | 中国科学院上海有机化学研究所 | 一种合成醋酸孕烯酮醇及其同类物的方法 |
CN103772464A (zh) * | 2013-12-30 | 2014-05-07 | 中国科学院理化技术研究所 | 利用蓝色led光源光敏氧化制备16-脱氢孕甾双烯酮醇醋酸酯类化合物的方法 |
CN112898366A (zh) * | 2021-01-13 | 2021-06-04 | 新疆大学 | 一种16-脱氢孕甾双烯酮醇醋酸酯类化合物及制备方法 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1120844C (zh) * | 2000-12-22 | 2003-09-10 | 中国科学院上海有机化学研究所 | 内酯化合物、合成方法及其用途 |
ES2212912B1 (es) * | 2003-01-22 | 2005-10-01 | Crystal Pharma, S.A. | Procedimiento para la obtencion de 17alfa-acetoxi-11beta-(4-n,n-dimetilaminofenil)-19-norpregna-4,9-dien-3,20-diona. |
CN1274708C (zh) * | 2004-06-21 | 2006-09-13 | 天津药业研究院有限公司 | 对雄甾类化合物进行17位接侧链的制备方法 |
-
2005
- 2005-06-20 CN CNB2005100119666A patent/CN100469786C/zh not_active Expired - Fee Related
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101974057A (zh) * | 2010-10-13 | 2011-02-16 | 天津大学 | 醋酸妊娠双烯醇酮及其同类物的绿色制备方法 |
CN102153611A (zh) * | 2011-02-18 | 2011-08-17 | 中国科学院上海有机化学研究所 | 一种合成醋酸孕烯酮醇及其同类物的方法 |
CN102153611B (zh) * | 2011-02-18 | 2012-11-28 | 中国科学院上海有机化学研究所 | 一种合成醋酸孕烯酮醇及其同类物的方法 |
CN103772464A (zh) * | 2013-12-30 | 2014-05-07 | 中国科学院理化技术研究所 | 利用蓝色led光源光敏氧化制备16-脱氢孕甾双烯酮醇醋酸酯类化合物的方法 |
CN112898366A (zh) * | 2021-01-13 | 2021-06-04 | 新疆大学 | 一种16-脱氢孕甾双烯酮醇醋酸酯类化合物及制备方法 |
Also Published As
Publication number | Publication date |
---|---|
CN100469786C (zh) | 2009-03-18 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Xiao et al. | Selenium-catalyzed selective reactions of carbonyl derivatives: state-of-the-art and future challenges | |
Moghaddam et al. | Rapid and efficient one-pot synthesis of 1, 4-dihydropyridine and polyhydroquinoline derivatives through the Hantzsch four component condensation by zinc oxide | |
CN100469786C (zh) | 合成16-脱氢孕甾双烯酮醇醋酸酯或同类物的方法 | |
CN113563370B (zh) | 一种壳聚糖负载铜材料催化制备α位有取代基的β-硼基酮的制备方法 | |
CN1212321C (zh) | 工业合成雷尼酸锶盐及其水合物的新方法 | |
CN114920908B (zh) | 含芴酮的有机共轭聚合物及其在α-酮酯合成中的应用 | |
CN109456161B (zh) | 一种可见光催化氧化断裂碳碳键的方法 | |
CN100344597C (zh) | 一种催化氧化环己醇制备环己酮的方法 | |
CN1939953A (zh) | 用于制备聚酮的离子液体的微波合成方法 | |
Tavakolian et al. | Cu2O/TiO2 as a sustainable and recyclable photocatalyst for gram-scale synthesis of phenols in water | |
CN1221563C (zh) | 16-脱氢孕烯醇酮及其同类物的生产方法 | |
Xu et al. | Microwave-assisted solvent-free synthesis of 1, 1-diacetates catalyzed by SbCl 3 from aldehydes and acetic anhydride | |
Shi et al. | β-Cyclodextrin promoted oxidation of aldehydes to carboxylic acids in water | |
CN113275038B (zh) | 一种光催化氧化裂解木质素c-o键及苯环的方法 | |
CN111269202B (zh) | 一种光照条件下2,5-呋喃二甲醛的制备方法 | |
CN113583005A (zh) | 一种5,6-二氢吲哚并[2,3-b]吲哚的合成方法 | |
CN113198469A (zh) | 一种铜钛异质结光催化剂及其制备方法和应用 | |
Lei et al. | Catalyst‐Free Oxidation of Alcohols at Room Temperature Using Water as Solvent | |
CN114956968B (zh) | 一种羰基化合物的制备方法 | |
CN111777556B (zh) | 氧化法制备吖啶9-羧酸的方法 | |
CN105772101B (zh) | 1‑苯乙基硫脲修饰的Mn‑Anderson型杂多酸催化剂、制备方法及其应用 | |
CN114289077B (zh) | 一种染料敏化二氧化钛复合纤维的制备方法 | |
CN114213359B (zh) | 一种合成1-羟基吩噻嗪类化合物的方法 | |
CN111138411B (zh) | 一种噻吨酮类化合物的紫外光促进的合成方法 | |
CN108299138B (zh) | 一种可见光催化氧化胺类化合物合成亚胺类化合物的方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
EE01 | Entry into force of recordation of patent licensing contract |
Assignee: ANHUI CHEM BRINGHT BIOENGINEERING CO.,LTD. Assignor: Technical Institute of Physics and Chemistry Chinese Academy of Sciences Contract record no.: 2011340000443 Denomination of invention: Method for synthesizing 16-dehydropregndiketonic alcohol acetic ester and its analogs Granted publication date: 20090318 License type: Exclusive License Open date: 20061227 Record date: 20111205 |
|
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20090318 Termination date: 20170620 |
|
CF01 | Termination of patent right due to non-payment of annual fee |