JPS5925792B2 - ヘキサヒドロジベンゾピラノン類の立体特異的製造法とその中間体 - Google Patents
ヘキサヒドロジベンゾピラノン類の立体特異的製造法とその中間体Info
- Publication number
- JPS5925792B2 JPS5925792B2 JP52081489A JP8148977A JPS5925792B2 JP S5925792 B2 JPS5925792 B2 JP S5925792B2 JP 52081489 A JP52081489 A JP 52081489A JP 8148977 A JP8148977 A JP 8148977A JP S5925792 B2 JPS5925792 B2 JP S5925792B2
- Authority
- JP
- Japan
- Prior art keywords
- dimethyl
- acid
- trans
- dimethylheptyl
- cis
- 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
- 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 13
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000000543 intermediate Substances 0.000 title description 6
- 230000000707 stereoselective effect Effects 0.000 title 1
- 238000000034 method Methods 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 22
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 14
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 10
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 10
- 239000002841 Lewis acid Substances 0.000 claims description 9
- 150000007517 lewis acids Chemical class 0.000 claims description 9
- 229910015900 BF3 Inorganic materials 0.000 claims description 7
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 6
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000003849 aromatic solvent Substances 0.000 claims description 3
- 239000007810 chemical reaction solvent Substances 0.000 claims description 3
- 150000008282 halocarbons Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 51
- 239000000047 product Substances 0.000 description 41
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 36
- -1 hexahydrodibenzopyranone compound Chemical class 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- 239000000203 mixture Substances 0.000 description 28
- 239000002904 solvent Substances 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 22
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 18
- 235000017557 sodium bicarbonate Nutrition 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 17
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 13
- PBVMIPXCKZYJMA-UHFFFAOYSA-N bicyclo[3.1.1]hept-4-ene Chemical compound C1C2=CCCC1C2 PBVMIPXCKZYJMA-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 238000004809 thin layer chromatography Methods 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 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 8
- 239000003921 oil Substances 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 8
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 8
- XZFDKWMYCUEKSS-UHFFFAOYSA-N 6,6-Dimethylbicyclo[3.1.1]heptan-2-one Chemical compound C1C2C(C)(C)C1CCC2=O XZFDKWMYCUEKSS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- TUJQDYIBTVJMMM-UHFFFAOYSA-N (4-acetyloxy-6,6-dimethyl-4-bicyclo[3.1.1]hept-2-enyl) acetate Chemical compound CC(=O)OC1(OC(C)=O)C=CC2C(C)(C)C1C2 TUJQDYIBTVJMMM-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000013076 target substance Substances 0.000 description 5
- KRDHHMGOAHHUPH-UHFFFAOYSA-N (4-acetyloxy-4-bicyclo[3.1.1]hept-2-enyl) acetate Chemical compound CC(=O)OC1(OC(C)=O)C=CC2CC1C2 KRDHHMGOAHHUPH-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- 208000019901 Anxiety disease Diseases 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000036506 anxiety Effects 0.000 description 4
- 210000003169 central nervous system Anatomy 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- YFJDGZZRPOYOFP-UHFFFAOYSA-N (4-acetyloxy-6,6-dimethyl-2-bicyclo[3.1.1]hept-3-enyl) acetate Chemical compound CC(=O)OC1C=C(OC(C)=O)C2C(C)(C)C1C2 YFJDGZZRPOYOFP-UHFFFAOYSA-N 0.000 description 3
- XMHXPSAHLRZYKH-JOYOIKCWSA-N (4aR,6aR)-2,3,4,4a,6,6a-hexahydrobenzo[c]chromen-1-one Chemical class C1=CC=CC2=C3C(=O)CCC[C@H]3OC[C@@H]21 XMHXPSAHLRZYKH-JOYOIKCWSA-N 0.000 description 3
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000002085 enols Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- VOXMSDBFCQUNDP-UHFFFAOYSA-N (4-acetyloxy-2-bicyclo[3.1.1]hept-3-enyl) acetate Chemical class CC(=O)OC1C=C(OC(C)=O)C2CC1C2 VOXMSDBFCQUNDP-UHFFFAOYSA-N 0.000 description 2
- CZQBNTFHWGYINW-UHFFFAOYSA-N (4-acetyloxy-2-bicyclo[3.1.1]hept-4-enyl) acetate Chemical class CC(=O)OC1CC(OC(C)=O)=C2CC1C2 CZQBNTFHWGYINW-UHFFFAOYSA-N 0.000 description 2
- CVELEVINKSHGGZ-UHFFFAOYSA-N (4-acetyloxy-4-bicyclo[3.1.1]hept-5-enyl) acetate Chemical class CC(=O)OC1(OC(C)=O)CCC2C=C1C2 CVELEVINKSHGGZ-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- PMAXNHPFNDQMAO-UHFFFAOYSA-N bicyclo[3.1.1]heptan-4-one Chemical compound O=C1CCC2CC1C2 PMAXNHPFNDQMAO-UHFFFAOYSA-N 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- HASGOCLZFTZSTN-UHFFFAOYSA-N cyclohexane;hexane Chemical compound CCCCCC.C1CCCCC1 HASGOCLZFTZSTN-UHFFFAOYSA-N 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- IRMPFYJSHJGOPE-UHFFFAOYSA-N olivetol Chemical compound CCCCCC1=CC(O)=CC(O)=C1 IRMPFYJSHJGOPE-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 description 1
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 description 1
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- CZHYAAVLICZNRV-UHFFFAOYSA-N (4-bromophenyl)methanesulfonic acid Chemical compound OS(=O)(=O)CC1=CC=C(Br)C=C1 CZHYAAVLICZNRV-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- YPSATSMZFPOCKK-UHFFFAOYSA-N 1,2-dimethyl-6,6a,7,8,10,10a-hexahydrobenzo[c]chromen-9-one Chemical compound CC1=C(C2=C(OCC3C2CC(CC3)=O)C=C1)C YPSATSMZFPOCKK-UHFFFAOYSA-N 0.000 description 1
- 125000003660 2,3-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- FNTPCMPJXYNWGS-UHFFFAOYSA-N 2-[2,6-dihydroxy-4-(2-methyloctan-2-yl)phenyl]-6,6-dimethylbicyclo[3.1.1]heptan-4-one Chemical compound OC1=CC(C(C)(C)CCCCCC)=CC(O)=C1C1C(C2(C)C)CC2C(=O)C1 FNTPCMPJXYNWGS-UHFFFAOYSA-N 0.000 description 1
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical class O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 1
- IIOGNJXZUWLLPZ-UHFFFAOYSA-N 3,5-dimethylbicyclo[3.1.1]heptan-4-one Chemical compound O=C1C(C)CC2CC1(C)C2 IIOGNJXZUWLLPZ-UHFFFAOYSA-N 0.000 description 1
- PJHYOCWMKYASAB-UHFFFAOYSA-N 4-pentylbenzene-1,3-diol Chemical compound CCCCCC1=CC=C(O)C=C1O PJHYOCWMKYASAB-UHFFFAOYSA-N 0.000 description 1
- 101100499944 Arabidopsis thaliana POL2A gene Proteins 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 description 1
- 101100028962 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) PDR1 gene Proteins 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- SEQIMZPSZATKQD-UHFFFAOYSA-N benzo[c]chromen-9-one Chemical compound C1=CC=C2C3=CC(=O)C=CC3=COC2=C1 SEQIMZPSZATKQD-UHFFFAOYSA-N 0.000 description 1
- 229930006722 beta-pinene Natural products 0.000 description 1
- 150000001591 beta-pinene derivatives Chemical class 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical group 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
-
- 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
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)
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Saccharide Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US000000740502 | 1976-11-10 | ||
| US05/740,502 US4102902A (en) | 1976-11-10 | 1976-11-10 | Stereoselective preparation of hexahydro dibenzopyranones and intermediates therefor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5359670A JPS5359670A (en) | 1978-05-29 |
| JPS5925792B2 true JPS5925792B2 (ja) | 1984-06-21 |
Family
ID=24976773
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP52081489A Expired JPS5925792B2 (ja) | 1976-11-10 | 1977-07-04 | ヘキサヒドロジベンゾピラノン類の立体特異的製造法とその中間体 |
| JP57064621A Expired JPS5912654B2 (ja) | 1976-11-10 | 1982-04-16 | 光学活性ノルピネン誘導体およびその製造法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57064621A Expired JPS5912654B2 (ja) | 1976-11-10 | 1982-04-16 | 光学活性ノルピネン誘導体およびその製造法 |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US4102902A (en, 2012) |
| JP (2) | JPS5925792B2 (en, 2012) |
| AT (1) | AT356103B (en, 2012) |
| AU (1) | AU509355B2 (en, 2012) |
| BE (1) | BE856413A (en, 2012) |
| BG (2) | BG28061A3 (en, 2012) |
| CA (1) | CA1101875A (en, 2012) |
| CH (2) | CH632506A5 (en, 2012) |
| CS (1) | CS196376B2 (en, 2012) |
| DD (2) | DD140455A5 (en, 2012) |
| DE (3) | DE2760006C2 (en, 2012) |
| DK (1) | DK301477A (en, 2012) |
| ES (3) | ES460387A1 (en, 2012) |
| FR (1) | FR2370742A1 (en, 2012) |
| GB (2) | GB1584182A (en, 2012) |
| GR (1) | GR66417B (en, 2012) |
| HU (2) | HU183286B (en, 2012) |
| IE (1) | IE45247B1 (en, 2012) |
| IL (3) | IL52427A (en, 2012) |
| MX (1) | MX5172E (en, 2012) |
| NL (1) | NL7707467A (en, 2012) |
| NZ (1) | NZ184526A (en, 2012) |
| PH (3) | PH13827A (en, 2012) |
| PL (2) | PL104432B1 (en, 2012) |
| PT (1) | PT66746B (en, 2012) |
| RO (1) | RO78780A (en, 2012) |
| SE (3) | SE428020B (en, 2012) |
| SU (2) | SU786898A3 (en, 2012) |
| YU (1) | YU163677A (en, 2012) |
| ZA (1) | ZA773960B (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0315035A (ja) * | 1989-03-03 | 1991-01-23 | Konica Corp | カメラ |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL55274A (en) * | 1978-08-02 | 1982-08-31 | Yissum Res Dev Co | 4-(2,6-dihydroxy-4-(dimethylheptyl)phenyl)substituted 2-pinen-10-ol and pinane derivatives,their preparation and pharmaceutical compositions comprising them |
| US4939169A (en) * | 1985-09-20 | 1990-07-03 | The Upjohn Company | 1,4-naphthalenediol and 1,4-hydroquinone derivatives |
| JPS63501288A (ja) * | 1985-09-20 | 1988-05-19 | ジ・アップジョン・カンパニ− | １，４−ナフタレンジオ−ルおよび１，４−ヒドロキノン誘導体 |
| IL80411A (en) * | 1986-10-24 | 1991-08-16 | Raphael Mechoulam | Preparation of dibenzopyranol derivatives and pharmaceutical compositions containing them |
| JP2577671B2 (ja) * | 1990-06-11 | 1997-02-05 | 高砂熱学工業株式会社 | 気化式精密加湿装置 |
| ATE247097T1 (de) * | 1998-05-04 | 2003-08-15 | Univ Connecticut | Analgetische und immunomodulierende cannabinoiden |
| US7589220B2 (en) * | 1998-06-09 | 2009-09-15 | University Of Connecticut | Inhibitors of the anandamide transporter |
| US7897598B2 (en) * | 1998-06-09 | 2011-03-01 | Alexandros Makriyannis | Inhibitors of the anandamide transporter |
| US7161016B1 (en) | 1998-11-24 | 2007-01-09 | University Of Connecticut | Cannabimimetic lipid amides as useful medications |
| US7276613B1 (en) | 1998-11-24 | 2007-10-02 | University Of Connecticut | Retro-anandamides, high affinity and stability cannabinoid receptor ligands |
| US7741365B2 (en) * | 1999-10-18 | 2010-06-22 | University Of Connecticut | Peripheral cannabinoid receptor (CB2) selective ligands |
| DE60033545T2 (de) * | 1999-10-18 | 2007-10-31 | The University Of Connecticut, Farmington | Neue bizyklische cannabinoid-agonisten für den cannabinoid-rezeptor |
| US7119108B1 (en) * | 1999-10-18 | 2006-10-10 | University Of Connecticut | Pyrazole derivatives as cannabinoid receptor antagonists |
| US6943266B1 (en) * | 1999-10-18 | 2005-09-13 | University Of Connecticut | Bicyclic cannabinoid agonists for the cannabinoid receptor |
| EP1223808B1 (en) | 1999-10-18 | 2007-03-07 | The University Of Connecticut | Peripheral cannabinoid receptor (cb2) selective ligands |
| US8084467B2 (en) * | 1999-10-18 | 2011-12-27 | University Of Connecticut | Pyrazole derivatives as cannabinoid receptor antagonists |
| US6900236B1 (en) * | 1999-10-18 | 2005-05-31 | University Of Connecticut | Cannabimimetic indole derivatives |
| US7393842B2 (en) * | 2001-08-31 | 2008-07-01 | University Of Connecticut | Pyrazole analogs acting on cannabinoid receptors |
| EP1361876A4 (en) * | 2001-01-26 | 2004-03-31 | Univ Connecticut | NEW CANNABIMIMETIC LIGANDS |
| JP2005503998A (ja) | 2001-01-29 | 2005-02-10 | ユニバーシティ オブ コネチカット | 受容体選択性のカンナビミメティックアミノアルキルインドール |
| JP4312594B2 (ja) * | 2001-07-13 | 2009-08-12 | ユニバーシティ オブ コネチカット | 新規な二環式及び三環式カンナビノイド |
| JP2005510492A (ja) * | 2001-10-26 | 2005-04-21 | ユニバーシティ オブ コネチカット | 新規な種類の効力のあるカンナビミメティックリガンド |
| WO2003091189A1 (en) * | 2002-04-25 | 2003-11-06 | Virginia Commonwealth University | Cannabinoids |
| WO2004017922A2 (en) | 2002-08-23 | 2004-03-04 | University Of Connecticut | Keto cannabinoids with therapeutic indications |
| EP2578577A1 (en) * | 2005-09-29 | 2013-04-10 | Albany Molecular Research, Inc. | Sulfonyl esters of tetrahydrocannabinol and derivatives thereof |
| US9763894B2 (en) * | 2006-12-05 | 2017-09-19 | Virginia Commonwealth University | Inflammation therapy |
| PL222532B1 (pl) | 2012-04-05 | 2016-08-31 | Akademia Morska W Szczecinie | Sposób i układ do diagnozowania układu wtryskowego silników o zapłonie samoczynnym, zwłaszcza silników okrętowych |
| US12029718B2 (en) | 2021-11-09 | 2024-07-09 | Cct Sciences, Llc | Process for production of essentially pure delta-9-tetrahydrocannabinol |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3856822A (en) * | 1973-07-18 | 1974-12-24 | Smithkline Corp | 3-alkenyl dibenzo (b,d)pyrans |
| US3856820A (en) * | 1973-07-18 | 1974-12-24 | Smithkline Corp | 2-AMINOMETHYL DIBENZO (b,d) PYRANS |
| US3856821A (en) * | 1973-07-18 | 1974-12-24 | Smithkline Corp | ALKOXY DIBENZO (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 |
-
1976
- 1976-11-10 US US05/740,502 patent/US4102902A/en not_active Expired - Lifetime
-
1977
- 1977-06-29 GB GB1144/80A patent/GB1584182A/en not_active Expired
- 1977-06-29 GB GB27138/77A patent/GB1584181A/en not_active Expired
- 1977-06-30 CA CA281,784A patent/CA1101875A/en not_active Expired
- 1977-06-30 NZ NZ184526A patent/NZ184526A/xx unknown
- 1977-06-30 ZA ZA00773960A patent/ZA773960B/xx unknown
- 1977-06-30 SE SE7707633A patent/SE428020B/xx not_active IP Right Cessation
- 1977-06-30 PH PH19935A patent/PH13827A/en unknown
- 1977-06-30 PT PT66746A patent/PT66746B/pt unknown
- 1977-06-30 IL IL52427A patent/IL52427A/xx unknown
- 1977-07-01 YU YU01636/77A patent/YU163677A/xx unknown
- 1977-07-01 BG BG036778A patent/BG28061A3/xx unknown
- 1977-07-01 BG BG037819A patent/BG28411A4/xx unknown
- 1977-07-01 DE DE2760006A patent/DE2760006C2/de not_active Expired
- 1977-07-01 AU AU26684/77A patent/AU509355B2/en not_active Expired
- 1977-07-01 DE DE2729859A patent/DE2729859C2/de not_active Expired
- 1977-07-01 DE DE2760005A patent/DE2760005C2/de not_active Expired
- 1977-07-04 JP JP52081489A patent/JPS5925792B2/ja not_active Expired
- 1977-07-04 ES ES460387A patent/ES460387A1/es not_active Expired
- 1977-07-04 SU SU772497362A patent/SU786898A3/ru active
- 1977-07-04 ES ES460389A patent/ES460389A1/es not_active Expired
- 1977-07-04 BE BE1008247A patent/BE856413A/xx not_active IP Right Cessation
- 1977-07-04 CH CH819477A patent/CH632506A5/de not_active IP Right Cessation
- 1977-07-04 PL PL1977206420A patent/PL104432B1/pl unknown
- 1977-07-04 ES ES460388A patent/ES460388A1/es not_active Expired
- 1977-07-04 MX MX775872U patent/MX5172E/es unknown
- 1977-07-04 PL PL1977199362A patent/PL104356B1/pl unknown
- 1977-07-05 GR GR53879A patent/GR66417B/el unknown
- 1977-07-05 IE IE1389/77A patent/IE45247B1/en unknown
- 1977-07-05 HU HU81113A patent/HU183286B/hu unknown
- 1977-07-05 HU HU77EI755A patent/HU177308B/hu unknown
- 1977-07-05 DD DD77208796A patent/DD140455A5/de unknown
- 1977-07-05 RO RO7798966A patent/RO78780A/ro unknown
- 1977-07-05 DK DK301477A patent/DK301477A/da not_active Application Discontinuation
- 1977-07-05 DD DD77199899A patent/DD134350A5/xx unknown
- 1977-07-05 FR FR7720645A patent/FR2370742A1/fr active Granted
- 1977-07-05 NL NL7707467A patent/NL7707467A/xx not_active Application Discontinuation
- 1977-07-06 AT AT483677A patent/AT356103B/de not_active IP Right Cessation
- 1977-07-06 CS CS774518A patent/CS196376B2/cs unknown
- 1977-10-28 PH PH20381A patent/PH13890A/en unknown
- 1977-10-28 PH PH20382A patent/PH14708A/en unknown
-
1978
- 1978-07-06 SU SU782633652A patent/SU1128829A3/ru active
-
1980
- 1980-07-15 IL IL60590A patent/IL60590A0/xx unknown
- 1980-07-15 IL IL60589A patent/IL60589A0/xx unknown
- 1980-07-22 SE SE8005314A patent/SE8005314L/sv not_active Application Discontinuation
- 1980-07-22 SE SE8005316A patent/SE434510B/sv unknown
-
1982
- 1982-02-05 CH CH71882A patent/CH632481A5/de not_active IP Right Cessation
- 1982-04-16 JP JP57064621A patent/JPS5912654B2/ja not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0315035A (ja) * | 1989-03-03 | 1991-01-23 | Konica Corp | カメラ |
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