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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (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) | ES460381A1 (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 (4)
| 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 |
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 |
| US3968125A (en) * | 1973-11-05 | 1976-07-06 | Eli Lilly And Company | Dihydroxyhexahydrodibenzo[b,d]pyrans |
| 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 |
| 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 SE SE7707629A patent/SE428016B/xx not_active IP Right Cessation
- 1977-06-30 IL IL52423A patent/IL52423A/xx unknown
- 1977-06-30 ZA ZA00773955A patent/ZA773955B/xx unknown
- 1977-06-30 PT PT66742A patent/PT66742B/pt unknown
- 1977-06-30 CA CA281,764A patent/CA1090813A/en not_active Expired
- 1977-06-30 NZ NZ184530A patent/NZ184530A/xx unknown
- 1977-06-30 PH PH19936A patent/PH12637A/en unknown
- 1977-07-01 DE DE2759994A patent/DE2759994C2/de not_active Expired
- 1977-07-01 DE DE2729846A patent/DE2729846C2/de not_active Expired
- 1977-07-01 BG BG037943A patent/BG28564A4/xx unknown
- 1977-07-01 BG BG036779A patent/BG28062A3/xx unknown
- 1977-07-01 YU YU01632/77A patent/YU163277A/xx unknown
- 1977-07-01 AU AU26680/77A patent/AU509540B2/en not_active Expired
- 1977-07-04 AR AR268306A patent/AR221210A1/es active
- 1977-07-04 PL PL1977199365A patent/PL105356B1/pl unknown
- 1977-07-04 ES ES460381A patent/ES460381A1/es not_active Expired
- 1977-07-04 SU SU772497360A patent/SU910121A3/ru active
- 1977-07-04 CH CH818977A patent/CH633791A5/de not_active IP Right Cessation
- 1977-07-04 BE BE1008242A patent/BE856408A/xx not_active IP Right Cessation
- 1977-07-04 ES ES460382A patent/ES460382A1/es not_active Expired
- 1977-07-04 JP JP52081484A patent/JPS5943465B2/ja not_active Expired
- 1977-07-05 NL NLAANVRAGE7707465,A patent/NL180316C/xx not_active IP Right Cessation
- 1977-07-05 GR GR53875A patent/GR66413B/el unknown
- 1977-07-05 IE IE1384/77A patent/IE45242B1/en unknown
- 1977-07-05 RO RO7798722A patent/RO78107A/ro unknown
- 1977-07-05 DD DD7700199901A patent/DD132495A5/xx unknown
- 1977-07-05 HU HU77EI751A patent/HU177307B/hu unknown
- 1977-07-05 HU HU81128A patent/HU183288B/hu unknown
- 1977-07-05 FR FR7720640A patent/FR2361384A1/fr active Granted
- 1977-07-05 DK DK301177A patent/DK144885C/da active
- 1977-07-05 DD DD77206148A patent/DD137228A5/xx unknown
- 1977-07-06 CS CS774514A patent/CS196374B2/cs unknown
- 1977-07-06 AT AT483277A patent/AT353268B/de not_active IP Right Cessation
- 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
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