CN1143361A - 苯乙酸衍生物及其制备和中间体以及含有它们的组合物 - Google Patents

Info

Publication number

CN1143361A

CN1143361A CN95191959.8A CN95191959A CN1143361A CN 1143361 A CN1143361 A CN 1143361A CN 95191959 A CN95191959 A CN 95191959A CN 1143361 A CN1143361 A CN 1143361A

Authority

CN

China

Prior art keywords

radical

alkylamino

group

alkyl

bis

Prior art date

1994-02-04

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.)

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• 238000000034 method Methods 0.000 title claims abstract description 21
• 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
• 230000008569 process Effects 0.000 title abstract description 10
• IXOFPUCWZCAFJX-UHFFFAOYSA-N 2-phenylethanethioic s-acid Chemical class SC(=O)CC1=CC=CC=C1 IXOFPUCWZCAFJX-UHFFFAOYSA-N 0.000 title abstract 2
• 239000013067 intermediate product Substances 0.000 title abstract 2
• 239000003795 chemical substances by application Substances 0.000 title description 3
• -1 cyano, nitro, hydroxy, amino Chemical group 0.000 claims abstract description 985
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 35
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 33
• 150000002367 halogens Chemical class 0.000 claims abstract description 33
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 28
• 239000001257 hydrogen Substances 0.000 claims abstract description 25
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
• 125000003118 aryl group Chemical group 0.000 claims abstract description 23
• 125000004104 aryloxy group Chemical group 0.000 claims abstract description 20
• 125000005110 aryl thio group Chemical group 0.000 claims abstract description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
• 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 11
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 10
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims abstract description 9
• 150000003839 salts Chemical class 0.000 claims abstract description 9
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 8
• 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 6
• 125000006323 alkenyl amino group Chemical group 0.000 claims abstract description 5
• 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 5
• 125000005129 aryl carbonyl group Chemical group 0.000 claims abstract description 5
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 5
• 125000004468 heterocyclylthio group Chemical group 0.000 claims abstract description 5
• 125000001769 aryl amino group Chemical group 0.000 claims abstract description 4
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
• 150000002431 hydrogen Chemical class 0.000 claims abstract 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2702
• 150000001875 compounds Chemical class 0.000 claims description 97
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 68
• 150000003254 radicals Chemical class 0.000 claims description 40
• 239000000203 mixture Substances 0.000 claims description 28
• 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims description 26
• 229910052757 nitrogen Inorganic materials 0.000 claims description 25
• 229910052717 sulfur Inorganic materials 0.000 claims description 25
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
• 238000006243 chemical reaction Methods 0.000 claims description 20
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• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 15
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 13
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 13
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• 125000005368 heteroarylthio group Chemical group 0.000 claims description 13
• 239000011593 sulfur Substances 0.000 claims description 13
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• 241000233866 Fungi Species 0.000 claims description 12
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 12
• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 12
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
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• 239000001301 oxygen Substances 0.000 claims description 9
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
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• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 7
• 239000002253 acid Substances 0.000 claims description 7
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• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
• 239000000126 substance Substances 0.000 claims description 6
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
• 125000001424 substituent group Chemical group 0.000 claims description 5
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• 125000004670 alkyl amino thio carbonyl group Chemical group 0.000 claims description 4
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• 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 4
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 3
• 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 3
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• 125000004122 cyclic group Chemical group 0.000 claims description 3
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• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 2
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• 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 2
• 239000004215 Carbon black (E152) Substances 0.000 claims description 2
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• 229930195733 hydrocarbon Natural products 0.000 claims description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
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• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
• 125000005418 aryl aryl group Chemical group 0.000 claims 2
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• 125000005325 aryloxy aryl group Chemical group 0.000 claims 1
• 150000005837 radical ions Chemical class 0.000 claims 1
• 125000005108 alkenylthio group Chemical group 0.000 abstract description 3
• 125000006193 alkinyl group Chemical group 0.000 abstract description 3
• 125000004465 cycloalkenyloxy group Chemical group 0.000 abstract description 3
• 125000000000 cycloalkoxy group Chemical group 0.000 abstract description 3
• 125000006310 cycloalkyl amino group Chemical group 0.000 abstract description 3
• 125000005366 cycloalkylthio group Chemical group 0.000 abstract description 3
• 125000005090 alkenylcarbonyl group Chemical group 0.000 abstract description 2
• 125000004448 alkyl carbonyl group Chemical group 0.000 abstract description 2
• 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract description 2
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• 125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
• 125000004438 haloalkoxy group Chemical group 0.000 abstract description 2
• 125000003107 substituted aryl group Chemical group 0.000 abstract description 2
• 125000004663 dialkyl amino group Chemical group 0.000 abstract 2
• 125000000547 substituted alkyl group Chemical group 0.000 abstract 2
• 125000001188 haloalkyl group Chemical group 0.000 abstract 1
• 125000005346 substituted cycloalkyl group Chemical group 0.000 abstract 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 236
• QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 197
• OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 196
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 168
• 239000000460 chlorine Substances 0.000 description 152
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 149
• WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 98
• 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 95
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 93
• RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical group [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 89
• 125000004432 carbon atom Chemical group C* 0.000 description 37
• 125000004433 nitrogen atom Chemical group N* 0.000 description 30
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 19
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• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 17
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