HU180635B - Process for producing 3-substituted-2-cyclopentanoe derivatives - Google Patents
Process for producing 3-substituted-2-cyclopentanoe derivatives Download PDFInfo
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- HU180635B HU180635B HU163181A HU163181A HU180635B HU 180635 B HU180635 B HU 180635B HU 163181 A HU163181 A HU 163181A HU 163181 A HU163181 A HU 163181A HU 180635 B HU180635 B HU 180635B
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- Hungary
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- lithium
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- 238000000034 method Methods 0.000 title claims description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- -1 3-Substituted-2-cyclopentenone Chemical class 0.000 claims abstract description 18
- 238000002360 preparation method Methods 0.000 claims abstract description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 239000002585 base Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000000010 aprotic solvent Substances 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 4
- SMKDPQDICUEFRX-UHFFFAOYSA-N dodecane-2,5-dione Chemical class CCCCCCCC(=O)CCC(C)=O SMKDPQDICUEFRX-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 39
- 239000011541 reaction mixture Substances 0.000 claims description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 13
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 10
- 229910052744 lithium Inorganic materials 0.000 claims description 10
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000012312 sodium hydride Substances 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims description 3
- 229910052987 metal hydride Inorganic materials 0.000 claims description 3
- 150000004681 metal hydrides Chemical class 0.000 claims description 3
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 2
- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- AHNJTQYTRPXLLG-UHFFFAOYSA-N lithium;diethylazanide Chemical compound [Li+].CC[N-]CC AHNJTQYTRPXLLG-UHFFFAOYSA-N 0.000 claims description 2
- ONDXXAPHPJPFKQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphoryl]-n-methylmethanamine;oxolane Chemical compound C1CCOC1.CN(C)P(=O)(N(C)C)N(C)C ONDXXAPHPJPFKQ-UHFFFAOYSA-N 0.000 claims 1
- 241000238631 Hexapoda Species 0.000 abstract description 5
- 239000000543 intermediate Substances 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229910000095 alkaline earth hydride Inorganic materials 0.000 abstract 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 14
- 229960004217 benzyl alcohol Drugs 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- 239000011780 sodium chloride Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 239000000284 extract Substances 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229940043279 diisopropylamine Drugs 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- KYMRHYIFGDKUTR-UHFFFAOYSA-N 3-(6-methoxy-2,6-dimethylheptyl)cyclopent-2-en-1-one Chemical compound COC(C)(C)CCCC(C)CC1=CC(=O)CC1 KYMRHYIFGDKUTR-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical compound O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 241000256118 Aedes aegypti Species 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 229910052805 deuterium Inorganic materials 0.000 description 2
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- UCSIFMPORANABL-SNVBAGLBSA-N (3r)-3,7-dimethyloctanal Chemical compound CC(C)CCC[C@@H](C)CC=O UCSIFMPORANABL-SNVBAGLBSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- GQOXGLGIJBSUPF-UHFFFAOYSA-N 1-chloro-2,6-dimethylheptane Chemical compound CC(C)CCCC(C)CCl GQOXGLGIJBSUPF-UHFFFAOYSA-N 0.000 description 1
- LLNQWCUHNLXCRX-UHFFFAOYSA-N 11-ethoxy-7,11-dimethyldodecane-2,5-dione Chemical compound CC(CC(CCC(C)=O)=O)CCCC(C)(OCC)C LLNQWCUHNLXCRX-UHFFFAOYSA-N 0.000 description 1
- OZDJORJWFCGQOV-UHFFFAOYSA-N 11-methoxy-7,11-dimethyldodecane-2,5-dione Chemical compound COC(C)(C)CCCC(C)CC(=O)CCC(C)=O OZDJORJWFCGQOV-UHFFFAOYSA-N 0.000 description 1
- JUUMAEXLYIMEOD-UHFFFAOYSA-N 2,6-dimethylhept-1-ene Chemical compound CC(C)CCCC(C)=C JUUMAEXLYIMEOD-UHFFFAOYSA-N 0.000 description 1
- RCYIBFNZRWQGNB-UHFFFAOYSA-N 2,6-dimethylheptan-1-ol Chemical compound CC(C)CCCC(C)CO RCYIBFNZRWQGNB-UHFFFAOYSA-N 0.000 description 1
- RTNBSTGXRDPDMN-UHFFFAOYSA-N 2-(3-benzyl-2-chloro-4-methyl-2H-1,3-thiazol-5-yl)ethanol Chemical compound C(C1=CC=CC=C1)N1C(SC(=C1C)CCO)Cl RTNBSTGXRDPDMN-UHFFFAOYSA-N 0.000 description 1
- IWSVLBKHBJGMAA-UHFFFAOYSA-M 2-(3-benzyl-4-methyl-1,3-thiazol-3-ium-5-yl)ethanol;chloride Chemical compound [Cl-].CC1=C(CCO)SC=[N+]1CC1=CC=CC=C1 IWSVLBKHBJGMAA-UHFFFAOYSA-M 0.000 description 1
- RLMZYXGKLIDPPD-UHFFFAOYSA-M 2-(3-ethyl-4-methyl-1,3-thiazol-3-ium-5-yl)ethanol;chloride Chemical compound [Cl-].CC[N+]1=CSC(CCO)=C1C RLMZYXGKLIDPPD-UHFFFAOYSA-M 0.000 description 1
- KGYKAVJUMFDTOR-UHFFFAOYSA-N 2-(6-methoxy-6-methylheptan-2-yl)-3-methylcyclopent-2-en-1-one Chemical compound COC(C)(C)CCCC(C)C1=C(C)CCC1=O KGYKAVJUMFDTOR-UHFFFAOYSA-N 0.000 description 1
- UVPDFYNNAVDCJM-UHFFFAOYSA-N 2-ethoxycyclopentan-1-one Chemical compound CCOC1CCCC1=O UVPDFYNNAVDCJM-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- FVVVUQDVHSCHQI-UHFFFAOYSA-N 3-(2,6-dimethylhept-5-enyl)cyclopent-2-en-1-one Chemical compound CC(C)=CCCC(C)CC1=CC(=O)CC1 FVVVUQDVHSCHQI-UHFFFAOYSA-N 0.000 description 1
- VTVPLUFBHGEVIS-UHFFFAOYSA-N 3-(2,6-dimethylheptyl)-3-hydroxycyclopentan-1-one Chemical compound CC(C)CCCC(C)CC1(O)CCC(=O)C1 VTVPLUFBHGEVIS-UHFFFAOYSA-N 0.000 description 1
- AMNFGIOEPHKNGO-UHFFFAOYSA-N 3-(2,6-dimethylheptyl)cyclopent-2-en-1-one Chemical compound CC(C)CCCC(C)CC1=CC(=O)CC1 AMNFGIOEPHKNGO-UHFFFAOYSA-N 0.000 description 1
- CHLVLGKIPHWKDU-UHFFFAOYSA-N 3-hydroxy-3-(6-methoxy-2,6-dimethylheptyl)cyclopentan-1-one Chemical compound COC(C)(C)CCCC(C)CC1(O)CCC(=O)C1 CHLVLGKIPHWKDU-UHFFFAOYSA-N 0.000 description 1
- ORDMNUYENQAQDJ-UHFFFAOYSA-N 4-hydroxy-4-(6-methoxy-2,6-dimethylheptyl)cyclopent-2-en-1-one Chemical compound CC(CC1(CC(C=C1)=O)O)CCCC(C)(OC)C ORDMNUYENQAQDJ-UHFFFAOYSA-N 0.000 description 1
- OLSHHRSPFWMAKQ-UHFFFAOYSA-N 7,11-dimethyldodec-10-ene-2,5-dione Chemical compound CC(C)=CCCC(C)CC(=O)CCC(C)=O OLSHHRSPFWMAKQ-UHFFFAOYSA-N 0.000 description 1
- IENPUAZTYALEFI-UHFFFAOYSA-N 7,11-dimethyldodecane-2,5-dione Chemical compound CC(C)CCCC(C)CC(=O)CCC(C)=O IENPUAZTYALEFI-UHFFFAOYSA-N 0.000 description 1
- IDWULKZGRNHZNR-UHFFFAOYSA-N 7-methoxy-3,7-dimethyloctanal Chemical compound COC(C)(C)CCCC(C)CC=O IDWULKZGRNHZNR-UHFFFAOYSA-N 0.000 description 1
- 241000252826 Brahmaea certhia Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- SWEMNEHFMJNRRD-UHFFFAOYSA-N CC(C(CCC(CCCCCC(C)OC)=O)=O)C Chemical compound CC(C(CCC(CCCCCC(C)OC)=O)=O)C SWEMNEHFMJNRRD-UHFFFAOYSA-N 0.000 description 1
- 244000166675 Cymbopogon nardus Species 0.000 description 1
- 235000018791 Cymbopogon nardus Nutrition 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010029897 Obsessive thoughts Diseases 0.000 description 1
- 241000254109 Tenebrio molitor Species 0.000 description 1
- 239000012445 acidic reagent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 229930003633 citronellal Natural products 0.000 description 1
- 235000000983 citronellal Nutrition 0.000 description 1
- NUUPJBRGQCEZSI-UHFFFAOYSA-N cyclopentane-1,3-diol Chemical compound OC1CCC(O)C1 NUUPJBRGQCEZSI-UHFFFAOYSA-N 0.000 description 1
- WZCNWCLFWMINNF-UHFFFAOYSA-N dodecane-2,3-dione Chemical compound CCCCCCCCCC(=O)C(C)=O WZCNWCLFWMINNF-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 230000009422 growth inhibiting effect Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000006197 hydroboration reaction Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- FYQGBXGJFWXIPP-UEVLXMDPSA-N hydroprene Chemical compound CCOC(=O)\C=C(/C)\C=C\CC(C)CCCC(C)C FYQGBXGJFWXIPP-UEVLXMDPSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- IXCKOXLJNNFOCM-UHFFFAOYSA-N n,n,2-triethylaniline Chemical compound CCN(CC)C1=CC=CC=C1CC IXCKOXLJNNFOCM-UHFFFAOYSA-N 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
- C07C45/66—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/73—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with hydrogenation
-
- 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
- C07C49/597—Unsaturated compounds containing a keto groups being part of a ring of a five-membered ring
-
- 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
- C07C49/647—Unsaturated compounds containing a keto groups being part of a ring having unsaturation outside the ring
-
- 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
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU163181A HU180635B (en) | 1981-06-02 | 1981-06-02 | Process for producing 3-substituted-2-cyclopentanoe derivatives |
| GB08215936A GB2100728B (en) | 1981-06-02 | 1982-06-01 | 3-substituted -2- cyclopentenone derivatives |
| PL23670782A PL135844B1 (en) | 1981-06-02 | 1982-06-01 | Method of obtaining derivatives of cyclopentenone -2 |
| CS405982A CS231994B2 (en) | 1981-06-02 | 1982-06-01 | Manufacturing process of 2-cyclopenane derivatives |
| FR8209546A FR2506757A1 (fr) | 1981-06-02 | 1982-06-02 | Procede de preparation de derives de 2-cyclopentenone substitues en position 3 et derives ainsi obtenus |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU163181A HU180635B (en) | 1981-06-02 | 1981-06-02 | Process for producing 3-substituted-2-cyclopentanoe derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU180635B true HU180635B (en) | 1983-03-28 |
Family
ID=10955414
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU163181A HU180635B (en) | 1981-06-02 | 1981-06-02 | Process for producing 3-substituted-2-cyclopentanoe derivatives |
Country Status (5)
| Country | Link |
|---|---|
| CS (1) | CS231994B2 (cs) |
| FR (1) | FR2506757A1 (cs) |
| GB (1) | GB2100728B (cs) |
| HU (1) | HU180635B (cs) |
| PL (1) | PL135844B1 (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2024000260A1 (en) * | 2022-06-29 | 2024-01-04 | Givaudan Sa | Organic compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4000174A (en) * | 1974-04-29 | 1976-12-28 | Zoecon Corporation | Novel compounds |
-
1981
- 1981-06-02 HU HU163181A patent/HU180635B/hu not_active IP Right Cessation
-
1982
- 1982-06-01 GB GB08215936A patent/GB2100728B/en not_active Expired
- 1982-06-01 CS CS405982A patent/CS231994B2/cs unknown
- 1982-06-01 PL PL23670782A patent/PL135844B1/pl unknown
- 1982-06-02 FR FR8209546A patent/FR2506757A1/fr active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB2100728B (en) | 1985-05-30 |
| CS231994B2 (en) | 1985-01-16 |
| GB2100728A (en) | 1983-01-06 |
| PL135844B1 (en) | 1985-12-31 |
| FR2506757A1 (fr) | 1982-12-03 |
| PL236707A1 (en) | 1983-04-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |