DE10260095A1 - Verfahren zur Herstellung von heterocyclischen Ketonen - Google Patents
Verfahren zur Herstellung von heterocyclischen Ketonen Download PDFInfo
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- DE10260095A1 DE10260095A1 DE10260095A DE10260095A DE10260095A1 DE 10260095 A1 DE10260095 A1 DE 10260095A1 DE 10260095 A DE10260095 A DE 10260095A DE 10260095 A DE10260095 A DE 10260095A DE 10260095 A1 DE10260095 A1 DE 10260095A1
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- carboxylic acid
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- 239000002253 acid Substances 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 title abstract description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title description 4
- 238000006116 polymerization reaction Methods 0.000 title description 3
- 150000001336 alkenes Chemical class 0.000 title description 2
- 239000012968 metallocene catalyst Substances 0.000 title description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title description 2
- 239000012024 dehydrating agents Substances 0.000 title 1
- -1 5-membered heterocyclic ketones Chemical class 0.000 claims abstract description 110
- 238000000034 method Methods 0.000 claims abstract description 29
- 150000007524 organic acids Chemical class 0.000 claims abstract description 14
- 239000007788 liquid Substances 0.000 claims abstract description 13
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 claims abstract description 7
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 6
- 230000000737 periodic effect Effects 0.000 claims abstract description 4
- 239000006096 absorbing agent Substances 0.000 claims abstract 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical group O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 239000012429 reaction media Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002250 absorbent Substances 0.000 claims description 6
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 6
- 230000002745 absorbent Effects 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000006575 electron-withdrawing group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 40
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 19
- 239000000047 product Substances 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 150000003254 radicals Chemical class 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 12
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 150000005840 aryl radicals Chemical class 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- JHNLZOVBAQWGQU-UHFFFAOYSA-N 380814_sial Chemical compound CS(O)(=O)=O.O=P(=O)OP(=O)=O JHNLZOVBAQWGQU-UHFFFAOYSA-N 0.000 description 6
- WTTUYECHLFHRHB-UHFFFAOYSA-N 5-methyl-3-(2-methylphenyl)-2-phenyl-4,5-dihydrocyclopenta[b]thiophen-6-one Chemical compound O=C1C(C)CC2=C1SC(C=1C=CC=CC=1)=C2C1=CC=CC=C1C WTTUYECHLFHRHB-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 229940098779 methanesulfonic acid Drugs 0.000 description 6
- 229920000137 polyphosphoric acid Polymers 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 5
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- YCZAEBYSGMULEM-UHFFFAOYSA-N 2,5-dimethyl-3-naphthalen-1-yl-4,5-dihydrocyclopenta[b]thiophen-6-one Chemical compound C1=CC=C2C(C3=C(C)SC4=C3CC(C4=O)C)=CC=CC2=C1 YCZAEBYSGMULEM-UHFFFAOYSA-N 0.000 description 4
- XQQBUAPQHNYYRS-UHFFFAOYSA-N 2-methylthiophene Chemical compound CC1=CC=CS1 XQQBUAPQHNYYRS-UHFFFAOYSA-N 0.000 description 4
- QENGPZGAWFQWCZ-UHFFFAOYSA-N Methylthiophene Natural products CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
- MWWYRYMDLMZFQO-UHFFFAOYSA-N 2,5-dimethyl-4,5-dihydrocyclopenta[b]thiophen-6-one Chemical compound C1=C(C)SC2=C1CC(C)C2=O MWWYRYMDLMZFQO-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- VOBWLFNYOWWARN-UHFFFAOYSA-N thiophen-3-one Chemical compound O=C1CSC=C1 VOBWLFNYOWWARN-UHFFFAOYSA-N 0.000 description 3
- 230000007306 turnover Effects 0.000 description 3
- QCFUDNJPYVMMOF-UHFFFAOYSA-N 2-methyl-3-naphthalen-1-ylthiophene Chemical compound S1C=CC(C=2C3=CC=CC=C3C=CC=2)=C1C QCFUDNJPYVMMOF-UHFFFAOYSA-N 0.000 description 2
- JTEDEZULZWWACE-UHFFFAOYSA-N 2-methyl-8-phenyl-1,2-dihydrocyclopenta[b][1]benzothiol-3-one Chemical compound O=C1C(C)CC(C=23)=C1SC3=CC=CC=2C1=CC=CC=C1 JTEDEZULZWWACE-UHFFFAOYSA-N 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- KVPBSBOTFRNKOM-UHFFFAOYSA-N 2h-cyclopenta[b]thiophene Chemical class C1=CC2=CCSC2=C1 KVPBSBOTFRNKOM-UHFFFAOYSA-N 0.000 description 2
- UZUBJHWKXMDIMI-UHFFFAOYSA-N 3-(2-methylphenyl)-2-phenylthiophene Chemical compound CC1=CC=CC=C1C1=C(C=2C=CC=CC=2)SC=C1 UZUBJHWKXMDIMI-UHFFFAOYSA-N 0.000 description 2
- NJCJOKLCLFCCON-UHFFFAOYSA-N 4-phenyl-1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1C1=CC=CC=C1 NJCJOKLCLFCCON-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- YEDVUDDWJVRKIS-UHFFFAOYSA-N cyclopenta[b]pyrrole Chemical class C1=C[C]2[N]C=CC2=C1 YEDVUDDWJVRKIS-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 235000015243 ice cream Nutrition 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- 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 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 0 *C1=C(*)C=C*1 Chemical compound *C1=C(*)C=C*1 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- LRMSQVBRUNSOJL-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)F LRMSQVBRUNSOJL-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- SIKZAAJIXSGHGX-UHFFFAOYSA-N 2-methyl-1,2-dihydrocyclopenta[b][1]benzothiol-3-one Chemical compound C1=CC=C2C(CC(C3=O)C)=C3SC2=C1 SIKZAAJIXSGHGX-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000005018 aryl alkenyl group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 230000001955 cumulated effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- LWRYDHOHXNQTSK-UHFFFAOYSA-N thiophene oxide Chemical compound O=S1C=CC=C1 LWRYDHOHXNQTSK-UHFFFAOYSA-N 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/56—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10260095A DE10260095A1 (de) | 2002-12-19 | 2002-12-19 | Verfahren zur Herstellung von heterocyclischen Ketonen |
| US10/539,683 US7531672B2 (en) | 2002-12-19 | 2003-12-17 | Preparation of heterocyclic ketones |
| DE60304608T DE60304608T2 (de) | 2002-12-19 | 2003-12-17 | Herstellung von heterocyclische ketone |
| AT03789303T ATE323078T1 (de) | 2002-12-19 | 2003-12-17 | Herstellung von heterocyclische ketone |
| EP03789303A EP1572677B1 (en) | 2002-12-19 | 2003-12-17 | Preparation of heterocyclic ketones |
| JP2005502543A JP2006511609A (ja) | 2002-12-19 | 2003-12-17 | 複素環ケトンの製造方法 |
| PCT/EP2003/014358 WO2004056796A1 (en) | 2002-12-19 | 2003-12-17 | Preparation of heterocyclic ketones |
| RU2005122647/04A RU2325383C2 (ru) | 2002-12-19 | 2003-12-17 | Получение гетероциклических кетонов |
| CN200380106670A CN100575351C (zh) | 2002-12-19 | 2003-12-17 | 杂环酮的制备 |
| AU2003293902A AU2003293902A1 (en) | 2002-12-19 | 2003-12-17 | Preparation of heterocyclic ketones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10260095A DE10260095A1 (de) | 2002-12-19 | 2002-12-19 | Verfahren zur Herstellung von heterocyclischen Ketonen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10260095A1 true DE10260095A1 (de) | 2004-07-01 |
Family
ID=32404078
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10260095A Withdrawn DE10260095A1 (de) | 2002-12-19 | 2002-12-19 | Verfahren zur Herstellung von heterocyclischen Ketonen |
| DE60304608T Expired - Lifetime DE60304608T2 (de) | 2002-12-19 | 2003-12-17 | Herstellung von heterocyclische ketone |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60304608T Expired - Lifetime DE60304608T2 (de) | 2002-12-19 | 2003-12-17 | Herstellung von heterocyclische ketone |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7531672B2 (https=) |
| EP (1) | EP1572677B1 (https=) |
| JP (1) | JP2006511609A (https=) |
| CN (1) | CN100575351C (https=) |
| AT (1) | ATE323078T1 (https=) |
| AU (1) | AU2003293902A1 (https=) |
| DE (2) | DE10260095A1 (https=) |
| RU (1) | RU2325383C2 (https=) |
| WO (1) | WO2004056796A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102924465B (zh) * | 2012-11-05 | 2015-02-18 | 郑州大学 | 手性呋喃并α,β-不饱和环酮、其制备方法及应用 |
| KR101789386B1 (ko) | 2014-12-26 | 2017-11-15 | 주식회사 엘지화학 | 고수율 및 고 광학순도의 광학활성 벤조티오펜계 화합물의 합성 방법 |
| CN115650952B (zh) * | 2022-11-02 | 2024-01-30 | 上海橡实化学有限公司 | 一种5,6-二氢环戊并[b]噻吩-4-酮的微波合成方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69525763T2 (de) * | 1994-04-11 | 2002-10-02 | Chugai Seiyaku K.K., Tokio/Tokyo | 4,6-DI-t-BUTYL-2,3-DIHYDROBENZOTHIOPHENE, DIE LDL OXIDATION HEMMEN |
| PL188107B1 (pl) | 1996-11-15 | 2004-12-31 | Montell Technology Company Bv | Metalocen, układ katalityczny do polimeryzacji, kationowe metaloceny, ligand oraz sposób polimeryzacji |
| US6444833B1 (en) * | 1999-12-15 | 2002-09-03 | Basell Technology Company Bv | Metallocene compounds, process for their preparation and their use in catalytic systems for the polymerization of olefins |
| JP4358470B2 (ja) * | 1999-12-28 | 2009-11-04 | バセル テクノロジー カンパニー ビー．ブイ． | メタロセン化合物、リガンド、触媒、ポリマーの製造方法及びプロピレンホモポリマー |
| DE60208683T2 (de) * | 2001-08-01 | 2006-11-02 | Basell Polyolefine Gmbh | Verfahren zur herstellung von heterocyclischen pentalen derivaten |
-
2002
- 2002-12-19 DE DE10260095A patent/DE10260095A1/de not_active Withdrawn
-
2003
- 2003-12-17 WO PCT/EP2003/014358 patent/WO2004056796A1/en not_active Ceased
- 2003-12-17 CN CN200380106670A patent/CN100575351C/zh not_active Expired - Fee Related
- 2003-12-17 EP EP03789303A patent/EP1572677B1/en not_active Expired - Lifetime
- 2003-12-17 DE DE60304608T patent/DE60304608T2/de not_active Expired - Lifetime
- 2003-12-17 RU RU2005122647/04A patent/RU2325383C2/ru not_active IP Right Cessation
- 2003-12-17 AU AU2003293902A patent/AU2003293902A1/en not_active Abandoned
- 2003-12-17 JP JP2005502543A patent/JP2006511609A/ja active Pending
- 2003-12-17 US US10/539,683 patent/US7531672B2/en not_active Expired - Lifetime
- 2003-12-17 AT AT03789303T patent/ATE323078T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2006511609A (ja) | 2006-04-06 |
| AU2003293902A1 (en) | 2004-07-14 |
| ATE323078T1 (de) | 2006-04-15 |
| US20070142649A1 (en) | 2007-06-21 |
| US7531672B2 (en) | 2009-05-12 |
| RU2005122647A (ru) | 2006-01-20 |
| CN1729184A (zh) | 2006-02-01 |
| EP1572677A1 (en) | 2005-09-14 |
| WO2004056796A1 (en) | 2004-07-08 |
| CN100575351C (zh) | 2009-12-30 |
| DE60304608D1 (de) | 2006-05-24 |
| RU2325383C2 (ru) | 2008-05-27 |
| DE60304608T2 (de) | 2006-11-02 |
| EP1572677B1 (en) | 2006-04-12 |
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| 8139 | Disposal/non-payment of the annual fee |