SU910121A3 - Способ получени производных гексагидродибензопиранона - Google Patents
Способ получени производных гексагидродибензопиранона Download PDFInfo
- Publication number
- SU910121A3 SU910121A3 SU772497360A SU2497360A SU910121A3 SU 910121 A3 SU910121 A3 SU 910121A3 SU 772497360 A SU772497360 A SU 772497360A SU 2497360 A SU2497360 A SU 2497360A SU 910121 A3 SU910121 A3 SU 910121A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- hydroxy
- formula
- cis
- dimethyl
- dibenzo
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 15
- XMHXPSAHLRZYKH-UHFFFAOYSA-N 2,3,4,4a,6,6a-hexahydrobenzo[c]chromen-1-one Chemical class C1=CC=CC2=C3C(=O)CCCC3OCC21 XMHXPSAHLRZYKH-UHFFFAOYSA-N 0.000 title claims description 3
- -1 5-substituted resorcinol Chemical class 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910015900 BF3 Inorganic materials 0.000 claims description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- RCZLCLVMJHKZAJ-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)cyclohex-3-en-1-one Chemical compound CC(C)(O)C1=CCC(=O)CC1 RCZLCLVMJHKZAJ-UHFFFAOYSA-N 0.000 abstract description 2
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- OOMFOSNMSRGHKV-UHFFFAOYSA-N 2-(2-methyloctan-2-yl)benzene-1,3-diol Chemical compound CCCCCCC(C)(C)C1=C(O)C=CC=C1O OOMFOSNMSRGHKV-UHFFFAOYSA-N 0.000 description 1
- GWBGUJWRDDDVBI-UHFFFAOYSA-N 5-(2-methyloctan-2-yl)benzene-1,3-diol Chemical compound CCCCCCC(C)(C)C1=CC(O)=CC(O)=C1 GWBGUJWRDDDVBI-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 101100476979 Rhodobacter capsulatus sdsA gene Proteins 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000006567 deketalization reaction Methods 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005907 ketalization reaction Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- VXGDDOCDUQOYEZ-UHFFFAOYSA-N trifluoroborane Chemical compound FB(F)F.FB(F)F VXGDDOCDUQOYEZ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Pyrane Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/702,804 US4054581A (en) | 1976-07-06 | 1976-07-06 | Preparation of cis-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-ones and intermediates therefor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU910121A3 true SU910121A3 (ru) | 1982-02-28 |
Family
ID=24822669
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772497360A SU910121A3 (ru) | 1976-07-06 | 1977-07-04 | Способ получени производных гексагидродибензопиранона |
| SU782632856A SU778712A3 (ru) | 1976-07-06 | 1978-07-06 | Способ получени кетал 4-(1-окси-1-метилэтил)-3-циклогексен-1-она |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782632856A SU778712A3 (ru) | 1976-07-06 | 1978-07-06 | Способ получени кетал 4-(1-окси-1-метилэтил)-3-циклогексен-1-она |
Country Status (30)
| Country | Link |
|---|---|
| US (2) | US4054581A (enExample) |
| JP (2) | JPS5943465B2 (enExample) |
| AR (1) | AR221210A1 (enExample) |
| AT (2) | AT353268B (enExample) |
| AU (1) | AU509540B2 (enExample) |
| BE (1) | BE856408A (enExample) |
| BG (2) | BG28564A4 (enExample) |
| CA (1) | CA1090813A (enExample) |
| CH (1) | CH633791A5 (enExample) |
| CS (1) | CS196374B2 (enExample) |
| DD (2) | DD132495A5 (enExample) |
| DE (2) | DE2759994C2 (enExample) |
| DK (1) | DK144885C (enExample) |
| ES (2) | ES460382A1 (enExample) |
| FR (1) | FR2361384A1 (enExample) |
| GB (1) | GB1582565A (enExample) |
| GR (1) | GR66413B (enExample) |
| HU (2) | HU177307B (enExample) |
| IE (1) | IE45242B1 (enExample) |
| IL (1) | IL52423A (enExample) |
| NL (1) | NL180316C (enExample) |
| NZ (1) | NZ184530A (enExample) |
| PH (2) | PH12637A (enExample) |
| PL (1) | PL105356B1 (enExample) |
| PT (1) | PT66742B (enExample) |
| RO (1) | RO78107A (enExample) |
| SE (2) | SE428016B (enExample) |
| SU (2) | SU910121A3 (enExample) |
| YU (1) | YU163277A (enExample) |
| ZA (1) | ZA773955B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4054581A (en) * | 1976-07-06 | 1977-10-18 | Eli Lilly And Company | Preparation of cis-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-ones and intermediates therefor |
| US4133816A (en) * | 1977-07-12 | 1979-01-09 | Eli Lilly And Company | Preparation of cis-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-ones and intermediates therefor |
| US4171315A (en) * | 1978-03-31 | 1979-10-16 | Eli Lilly And Company | Preparation of cis-hexahydrodibenzopyranones |
| US4395560A (en) * | 1982-05-24 | 1983-07-26 | Eli Lilly And Company | Preparation of 6a,10a-trans-hexahydrodibenzopyranones |
| JPH0681571B2 (ja) * | 1989-11-29 | 1994-10-19 | 株式会社備文 | 解し芝の連続定量供給装置 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3576887A (en) * | 1967-05-01 | 1971-04-27 | American Home Prod | Process for the preparation of oxaphenanthrenes and intermediates therefor |
| US3906047A (en) * | 1971-06-14 | 1975-09-16 | Hoffmann La Roche | 8-(2,6,6-Trimethyl-4-oxo-2-cyclohexen-1-ylidene-2-methylene-6-methyl-4,6-octadien-3-ol |
| US3929835A (en) * | 1973-08-29 | 1975-12-30 | Sharps Ass | Alkyl substituted cyclopenta benzopyrans |
| US3928598A (en) * | 1973-11-05 | 1975-12-23 | Lilly Co Eli | Hexahydro-dibenzo{8 b,d{9 pyran-9-ones as an anti-anxiety drug |
| US3968125A (en) * | 1973-11-05 | 1976-07-06 | Eli Lilly And Company | Dihydroxyhexahydrodibenzo[b,d]pyrans |
| US4054581A (en) | 1976-07-06 | 1977-10-18 | Eli Lilly And Company | Preparation of cis-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-ones and intermediates therefor |
-
1976
- 1976-07-06 US US05/702,804 patent/US4054581A/en not_active Expired - Lifetime
-
1977
- 1977-06-29 GB GB27139/77A patent/GB1582565A/en not_active Expired
- 1977-06-30 PH PH19936A patent/PH12637A/en unknown
- 1977-06-30 IL IL52423A patent/IL52423A/xx unknown
- 1977-06-30 PT PT66742A patent/PT66742B/pt unknown
- 1977-06-30 ZA ZA00773955A patent/ZA773955B/xx unknown
- 1977-06-30 NZ NZ184530A patent/NZ184530A/xx unknown
- 1977-06-30 CA CA281,764A patent/CA1090813A/en not_active Expired
- 1977-06-30 SE SE7707629A patent/SE428016B/xx not_active IP Right Cessation
- 1977-07-01 DE DE2759994A patent/DE2759994C2/de not_active Expired
- 1977-07-01 YU YU01632/77A patent/YU163277A/xx unknown
- 1977-07-01 AU AU26680/77A patent/AU509540B2/en not_active Expired
- 1977-07-01 BG BG037943A patent/BG28564A4/xx unknown
- 1977-07-01 BG BG036779A patent/BG28062A3/xx unknown
- 1977-07-01 DE DE2729846A patent/DE2729846C2/de not_active Expired
- 1977-07-04 PL PL1977199365A patent/PL105356B1/pl unknown
- 1977-07-04 BE BE1008242A patent/BE856408A/xx not_active IP Right Cessation
- 1977-07-04 CH CH818977A patent/CH633791A5/de not_active IP Right Cessation
- 1977-07-04 AR AR268306A patent/AR221210A1/es active
- 1977-07-04 ES ES460382A patent/ES460382A1/es not_active Expired
- 1977-07-04 ES ES460381A patent/ES460381A1/es not_active Expired
- 1977-07-04 JP JP52081484A patent/JPS5943465B2/ja not_active Expired
- 1977-07-04 SU SU772497360A patent/SU910121A3/ru active
- 1977-07-05 GR GR53875A patent/GR66413B/el unknown
- 1977-07-05 IE IE1384/77A patent/IE45242B1/en unknown
- 1977-07-05 FR FR7720640A patent/FR2361384A1/fr active Granted
- 1977-07-05 HU HU77EI751A patent/HU177307B/hu unknown
- 1977-07-05 DD DD7700199901A patent/DD132495A5/xx unknown
- 1977-07-05 DK DK301177A patent/DK144885C/da active
- 1977-07-05 RO RO7798722A patent/RO78107A/ro unknown
- 1977-07-05 HU HU81128A patent/HU183288B/hu unknown
- 1977-07-05 DD DD77206148A patent/DD137228A5/xx unknown
- 1977-07-05 NL NLAANVRAGE7707465,A patent/NL180316C/xx not_active IP Right Cessation
- 1977-07-06 AT AT483277A patent/AT353268B/de not_active IP Right Cessation
- 1977-07-06 CS CS774514A patent/CS196374B2/cs unknown
- 1977-07-12 US US05/814,817 patent/US4115403A/en not_active Expired - Lifetime
- 1977-11-18 PH PH20451A patent/PH13260A/en unknown
-
1978
- 1978-07-06 SU SU782632856A patent/SU778712A3/ru active
- 1978-12-19 AT AT908478A patent/AT355019B/de not_active IP Right Cessation
-
1980
- 1980-07-24 SE SE8005373A patent/SE435060B/sv not_active IP Right Cessation
-
1981
- 1981-02-17 JP JP56022855A patent/JPS6049196B2/ja not_active Expired
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1340752B1 (en) | Process for the production of semi synthetic statins via novel intermediates | |
| SU910121A3 (ru) | Способ получени производных гексагидродибензопиранона | |
| CA3174197A1 (en) | Catalytic cannabigerol processes and precursors | |
| Lhoták et al. | Synthesis of a deep-cavity thiacalix [4] arene | |
| GB2162179A (en) | Naphthyl analogs of mevalonolactone and derivatives thereof, processes for their production and their use | |
| IE48824B1 (en) | Aurone derivatives | |
| US4234490A (en) | Intermediates in the synthesis of vitamin E | |
| US4201879A (en) | Hydroquinones | |
| JP2022507668A (ja) | カンナビノイドを調製するための方法および化合物 | |
| KR100776102B1 (ko) | 포스핀 옥사이드 비타민 디 전구체 | |
| JP2718645B2 (ja) | ベンゾ複素環系の化合物、その製造方法及びそれを含有する組成物 | |
| US4131614A (en) | Process for preparing cis-hexahydrodibenzopyranones | |
| JPS5828877B2 (ja) | 新規２，６−ジメトキシ−４−置換フエニル・ジ置換ホスフエイト類 | |
| Batra et al. | Chemistry of 5 (2H)‐isoxazolones: Novel conversion of positional isomers | |
| EP0647640B1 (en) | Process for the preparation of pilocarpine derivatives | |
| SU726094A1 (ru) | Производные 5-оксибензофурана в качестве полупродуктов дл синтеза 2-фенил-3-ацил-4-аминометил-5-оксибензофуранов и способ их получени | |
| JP5057301B2 (ja) | ジアルキルシラノール化合物およびその製造方法 | |
| SU668598A3 (ru) | Способ получени оптически активных производных простагландинов,или их оптических антиподов,или их рацематов | |
| SU514831A1 (ru) | Способ получени производных оксазолидино-(3,2- ) пиридо (2,3- ) или оксазолидино (3,2- ) пиримидо (4,5- ) (1,4)тиазина | |
| JPH04279564A (ja) | スルホニル化合物およびビタミンａまたはそのエステルを製造する方法における中間体としての前記化合物使用 | |
| CA1132139A (en) | Dithienyl alkyl amines and process for their production | |
| Huang et al. | The reactions of tellurium tetrachloride with acetone | |
| SU493964A3 (ru) | Способ производных изоиндолина или их солей | |
| US2732396A (en) | Vitamin a intermediate | |
| KR810000428B1 (ko) | 2, 6-메타노-2h-1-벤즈옥소신 유도체의 제조방법 |