DE2508295A1 - Verfahren zur herstellung von methyljasmonat und von verwandten verbindungen - Google Patents
Verfahren zur herstellung von methyljasmonat und von verwandten verbindungenInfo
- Publication number
- DE2508295A1 DE2508295A1 DE19752508295 DE2508295A DE2508295A1 DE 2508295 A1 DE2508295 A1 DE 2508295A1 DE 19752508295 DE19752508295 DE 19752508295 DE 2508295 A DE2508295 A DE 2508295A DE 2508295 A1 DE2508295 A1 DE 2508295A1
- Authority
- DE
- Germany
- Prior art keywords
- compound
- formula
- methyl
- group
- coor
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 28
- 150000001875 compounds Chemical class 0.000 title claims description 24
- GEWDNTWNSAZUDX-WQMVXFAESA-N (-)-methyl jasmonate Chemical compound CC\C=C/C[C@@H]1[C@@H](CC(=O)OC)CCC1=O GEWDNTWNSAZUDX-WQMVXFAESA-N 0.000 title description 6
- GEWDNTWNSAZUDX-UHFFFAOYSA-N methyl 7-epi-jasmonate Natural products CCC=CCC1C(CC(=O)OC)CCC1=O GEWDNTWNSAZUDX-UHFFFAOYSA-N 0.000 title description 4
- -1 alkali metal cation Chemical class 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- 230000029936 alkylation Effects 0.000 claims description 4
- 238000005804 alkylation reaction Methods 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- BGTOWKSIORTVQH-HOSYLAQJSA-N cyclopentanone Chemical group O=[13C]1CCCC1 BGTOWKSIORTVQH-HOSYLAQJSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- NNTQQGRYWUZPQQ-UHFFFAOYSA-N 2-(3-oxocyclopentyl)acetic acid Chemical class OC(=O)CC1CCC(=O)C1 NNTQQGRYWUZPQQ-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 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 2
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 229940096405 magnesium cation Drugs 0.000 claims 2
- XXMSBKPCQHOXDU-UHFFFAOYSA-N CC(O)=O.O=C1CCC=C1 Chemical class CC(O)=O.O=C1CCC=C1 XXMSBKPCQHOXDU-UHFFFAOYSA-N 0.000 claims 1
- 150000001242 acetic acid derivatives Chemical class 0.000 claims 1
- 150000001336 alkenes Chemical group 0.000 claims 1
- 150000001940 cyclopentanes Chemical class 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 150000004702 methyl esters Chemical class 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000002168 alkylating agent Substances 0.000 description 4
- 229940100198 alkylating agent Drugs 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclo-pentanone Natural products O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- IRXBNHGNHKNOJI-UHFFFAOYSA-N butanedioyl dichloride Chemical compound ClC(=O)CCC(Cl)=O IRXBNHGNHKNOJI-UHFFFAOYSA-N 0.000 description 3
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- IBXNCJKFFQIKKY-UHFFFAOYSA-N 1-pentyne Chemical compound CCCC#C IBXNCJKFFQIKKY-UHFFFAOYSA-N 0.000 description 2
- WDNQGERQWDIEQI-UHFFFAOYSA-N 2-(2-methoxycarbonyl-3-oxocyclopenten-1-yl)acetic acid Chemical compound COC(=O)C1=C(CC(O)=O)CCC1=O WDNQGERQWDIEQI-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical compound O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 description 2
- YVHAIVPPUIZFBA-UHFFFAOYSA-N Cyclopentylacetic acid Chemical compound OC(=O)CC1CCCC1 YVHAIVPPUIZFBA-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- PJOXGFYPAYXBLO-UHFFFAOYSA-N dimethyl 3,6-dioxooctanedioate Chemical compound COC(=O)CC(=O)CCC(=O)CC(=O)OC PJOXGFYPAYXBLO-UHFFFAOYSA-N 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- UPZGJLYTRBYTLM-UHFFFAOYSA-M lithium;iodide;dihydrate Chemical compound [Li+].O.O.[I-] UPZGJLYTRBYTLM-UHFFFAOYSA-M 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- WWTULTKUWBKVGV-UHFFFAOYSA-M potassium;3-methoxy-3-oxopropanoate Chemical compound [K+].COC(=O)CC([O-])=O WWTULTKUWBKVGV-UHFFFAOYSA-M 0.000 description 2
- 150000007659 semicarbazones Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VDHGRVFJBGRHMD-UHFFFAOYSA-N 1-bromopent-2-yne Chemical compound CCC#CCBr VDHGRVFJBGRHMD-UHFFFAOYSA-N 0.000 description 1
- CGHIBGNXEGJPQZ-UHFFFAOYSA-N 1-hexyne Chemical compound CCCCC#C CGHIBGNXEGJPQZ-UHFFFAOYSA-N 0.000 description 1
- WOBQDAHHOULWAT-UHFFFAOYSA-N 2-(3-oxocyclopenten-1-yl)acetic acid Chemical compound OC(=O)CC1=CC(=O)CC1 WOBQDAHHOULWAT-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 102100035767 Adrenocortical dysplasia protein homolog Human genes 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- 101000929940 Homo sapiens Adrenocortical dysplasia protein homolog Proteins 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- VCONLICBYCAJEB-UHFFFAOYSA-N acetic acid;cyclopentanone Chemical compound CC(O)=O.O=C1CCCC1 VCONLICBYCAJEB-UHFFFAOYSA-N 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- NHVHYFAWHCJELN-UHFFFAOYSA-N benzene;n,n-dimethylformamide Chemical compound CN(C)C=O.C1=CC=CC=C1 NHVHYFAWHCJELN-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- GMVIQOCPXTZUFJ-UHFFFAOYSA-L dipotassium;2-ethylpropanedioate Chemical compound [K+].[K+].CCC(C([O-])=O)C([O-])=O GMVIQOCPXTZUFJ-UHFFFAOYSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- CHNUOJQWGUIOLD-NFZZJPOKSA-N epalrestat Chemical compound C=1C=CC=CC=1\C=C(/C)\C=C1/SC(=S)N(CC(O)=O)C1=O CHNUOJQWGUIOLD-NFZZJPOKSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- ILYZMVXPMXPOSW-UHFFFAOYSA-N ethyl 2-(2-ethoxy-2-oxoethyl)-1-hex-3-ynyl-5-oxocyclopentane-1-carboxylate Chemical compound CCOC(=O)CC1CCC(=O)C1(CCC#CCC)C(=O)OCC ILYZMVXPMXPOSW-UHFFFAOYSA-N 0.000 description 1
- XFXKZPNUWBTSHC-UHFFFAOYSA-N ethyl 2-(2-hex-3-enyl-3-oxocyclopentyl)acetate Chemical compound CCOC(=O)CC1CCC(=O)C1CCC=CCC XFXKZPNUWBTSHC-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- RZZAUHYVSHEOQJ-UHFFFAOYSA-N hex-2-ynyl methanesulfonate Chemical compound CCCC#CCOS(C)(=O)=O RZZAUHYVSHEOQJ-UHFFFAOYSA-N 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000010656 jasmine oil Substances 0.000 description 1
- 239000011981 lindlar catalyst Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- JNZAFMVFHZGMPY-UHFFFAOYSA-N methyl 1-but-2-ynyl-2-(2-methoxy-2-oxoethyl)-5-oxocyclopentane-1-carboxylate Chemical compound COC(=O)CC1CCC(=O)C1(CC#CC)C(=O)OC JNZAFMVFHZGMPY-UHFFFAOYSA-N 0.000 description 1
- BVOKJSUJYDTXMR-UHFFFAOYSA-N methyl 1-but-3-ynyl-2-(2-methoxy-2-oxoethyl)-5-oxocyclopentane-1-carboxylate Chemical compound COC(=O)CC1CCC(=O)C1(CCC#C)C(=O)OC BVOKJSUJYDTXMR-UHFFFAOYSA-N 0.000 description 1
- SDDNXSHBPDUGLE-UHFFFAOYSA-N methyl 1-hex-2-ynyl-2-(2-methoxy-2-oxoethyl)-5-oxocyclopentane-1-carboxylate Chemical compound CCCC#CCC1(C(=O)OC)C(CC(=O)OC)CCC1=O SDDNXSHBPDUGLE-UHFFFAOYSA-N 0.000 description 1
- RIUFXIPDMSRBSP-UHFFFAOYSA-N methyl 2-(2-hex-2-enyl-3-oxocyclopentyl)acetate Chemical compound CCCC=CCC1C(CC(=O)OC)CCC1=O RIUFXIPDMSRBSP-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/447,101 US4014919A (en) | 1974-03-01 | 1974-03-01 | Process for preparing methyl jasmonate and related compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2508295A1 true DE2508295A1 (de) | 1975-09-04 |
Family
ID=23775001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752508295 Pending DE2508295A1 (de) | 1974-03-01 | 1975-02-26 | Verfahren zur herstellung von methyljasmonat und von verwandten verbindungen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4014919A (en, 2012) |
| JP (1) | JPS50123645A (en, 2012) |
| BE (1) | BE826150A (en, 2012) |
| DE (1) | DE2508295A1 (en, 2012) |
| DK (1) | DK75675A (en, 2012) |
| FR (2) | FR2279717A1 (en, 2012) |
| NL (1) | NL7502396A (en, 2012) |
| SE (1) | SE7502310L (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2332971A1 (fr) * | 1975-11-26 | 1977-06-24 | Roussel Uclaf | Nouveaux derives de la cyclopentanone, leur procede de preparation et leur application a la synthese de prostaglandines |
| NL179368C (nl) * | 1976-07-16 | 1986-09-01 | Roure Bertrand Dupont Sa | Werkwijze voor het bereiden van oxocyclopentyl- en oxocyclohexylverbindingen. |
| JPS5432444A (en) * | 1977-08-12 | 1979-03-09 | Otsuka Chem Co Ltd | Preparation of cis-2-pentene derivative |
| JPS6036414B2 (ja) * | 1977-08-12 | 1985-08-20 | 大塚化学薬品株式会社 | ２−（２−ペンチニル）シクロペンタノ−ル誘導体及びその製造法 |
| GB1597866A (en) * | 1977-08-12 | 1981-09-16 | Otsuka Kagaku Yakuhin | 2-cyclopentone derivatives |
| EP0449445A3 (en) * | 1990-03-27 | 1993-08-25 | Pfizer Inc. | Preparation of beta-ketoesters useful in preparing quinolone antibiotics |
| US5728866A (en) * | 1994-06-23 | 1998-03-17 | Firmenich Sa | Process for the preparation of (+)-(1R) -cis-3-oxo-2-pentyl-1-cyclopentaneacetic acid |
| US6333180B1 (en) * | 1999-12-21 | 2001-12-25 | International Flavors & Fragrances Inc. | Bioprocess for the high-yield production of food flavor-acceptable jasmonic acid and methyl jasmonate |
-
1974
- 1974-03-01 US US05/447,101 patent/US4014919A/en not_active Expired - Lifetime
-
1975
- 1975-02-26 DE DE19752508295 patent/DE2508295A1/de active Pending
- 1975-02-26 DK DK75675*#A patent/DK75675A/da unknown
- 1975-02-28 JP JP50024908A patent/JPS50123645A/ja active Pending
- 1975-02-28 FR FR7506439A patent/FR2279717A1/fr active Granted
- 1975-02-28 SE SE7502310A patent/SE7502310L/xx unknown
- 1975-02-28 BE BE153887A patent/BE826150A/xx unknown
- 1975-02-28 NL NL7502396A patent/NL7502396A/xx unknown
- 1975-10-15 FR FR7531575A patent/FR2330668A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| US4014919A (en) | 1977-03-29 |
| FR2279717B3 (en, 2012) | 1977-11-10 |
| DK75675A (en, 2012) | 1975-09-02 |
| JPS50123645A (en, 2012) | 1975-09-29 |
| BE826150A (fr) | 1975-06-16 |
| NL7502396A (nl) | 1975-09-03 |
| SE7502310L (en, 2012) | 1975-09-02 |
| FR2330668A1 (fr) | 1977-06-03 |
| FR2279717A1 (fr) | 1976-02-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2008878C3 (en, 2012) | ||
| DE2315640B2 (de) | Verfahren zur Herstellung ungesättigter cycloaliphatischer Ketone und dabei gebildete cycloaliphatische Diketone und deren Enolate | |
| DE2508295A1 (de) | Verfahren zur herstellung von methyljasmonat und von verwandten verbindungen | |
| DE3918015A1 (de) | Verfahren zur herstellung von muscon, zwischenprodukte fuer dieses verfahren sowie deren herstellung | |
| DE2423485C2 (de) | 3-Oxotricyclo[2,2,1,0↑2↑↑,↑↑6↑]heptan-5-anti-carbonsäure und Verfahren zu ihrer Herstellung | |
| DE2429935C3 (de) | Verfahren zur Herstellung von 2,2,6,6- Tetramethyl-4-oxopiperidin | |
| DE2543870A1 (de) | Verfahren zur herstellung von 5-fluor-2-methyl-1-(p-methyl-sulfinylbenzyliden)-indenyl-3-essigsaeure | |
| DE2732107A1 (de) | Verfahren zur herstellung von cyclischen ketonen | |
| DE2245560A1 (de) | Verfahren zur herstellung von 4alkoxycarbonyl-2-thiazolinen | |
| CH494219A (de) | Verfahren zur Herstellung einer Androsten-Verbindung | |
| EP0061669B1 (de) | Verbessertes Verfahren zur Herstellung von Cyclohexan-1,3-dionen sowie einige neue bicyclische Cyclohexan-1,3-dione | |
| DE1951294C3 (de) | Verfahren zur Herstellung von 3-Hydroxy-2-methyl-y-pyron (Maltol) | |
| DE2600768C2 (de) | Verfahren zur Herstellung von 6,11-Dihydro-11-oxodibenz[b,e]-oxepin-alkansäuren | |
| DE899198C (de) | Verfahren zur Herstellung von kernalkylierten 2,4, 6-Trioxyacylophenonen | |
| DE2362363A1 (de) | Neue synthese von vincamin und seinen stereoisomeren | |
| EP0378073B1 (de) | Verfahren zur Herstellung von 1,3-Cyclopentandion | |
| EP0381624B1 (de) | Verfahren zur Herstellung von 1-Alkylthio- und 1-Benzylthio-1-formylcyclopropanen | |
| WO2010022953A2 (de) | Synthese von myrtucommulon a und myrtucommulon-analoga | |
| EP0206294B1 (de) | 3-Hydroxy-3-(2-Methyl-5-pyridyl)-propionsäurealkylester | |
| DE2731543B2 (de) | Verfahren zur Herstellung von Cyclopentadecanolid | |
| DE1593349C (en, 2012) | ||
| AT222816B (de) | Verfahren zur Herstellung von 2-cis-β-Jonylidenessigsäure | |
| DE2619321C2 (de) | Oxalsäurederivate, ihre Herstellung und ihre Verwendung | |
| DE2440745C3 (de) | Verfahren zur Abtrennung von cis-Chrysanthemummonocarbonsäure | |
| DE3003457A1 (de) | Verfahren zur herstellung von alpha -hydroxycarbonylverbindungen |