CAS: 4887-42-7; 2-(Hydroxymethyl)-4,5,6,7-Tetrahydro-1H-Isoindole-1,3(2H)-Dione

相似化合物

4720-86-9 28839-49-8 180971-97-5

上下游产品

formaldehyd 3,4,5,6-tetrahydrophthalimide 2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione

N-羟甲基邻苯二甲酰亚胺置于platinum On Activated Charcoal,氢气体系中,用 乙醇 作为反应溶剂,105.0~110.0 °C,1.8 Mpa 条件下,反应 12.0H,以93.7%的收率获得产物n-羟甲基-3,4,5,6-四氢邻苯二甲酰亚胺
参考文献:一种n-羟甲基-3,4,5,6-四氢邻苯二甲酰亚胺的合成方法
标题:一种n-羟甲基-3,4,5,6-四氢邻苯二甲酰亚胺的合成方法
摘要:本发明公开了一种n‑羟甲基‑3,4,5,6‑四氢邻苯二甲酰亚胺的合成方法,将邻苯二甲酰亚胺,四丁基溴化铵加入到水中,加毕滴加甲醛水溶液,滴毕保温反应,反应结束后脱干溶剂以丙酮水溶液重结晶,重结晶后料投入高压釜后加入pd/c,通氢气保温保压反应,反应结束后脱干溶剂以甲苯重结晶,该方法的两步合成收率可达到80%以上,产品液谱归一含量可达到97.6%.该方法中使用的溶剂经回收处理后可套用于反应系统内,还原催化剂可套用10次以上,本发明工艺过程简单,易操作,反应选择性强,产品收率,质量,能耗低,无含磷,含氮废水产生,生产现场环境得到显著改善,有利于工业化清洁生产.

专利信息

专利号:EP-0050534-B1
优先权日:1980-10-01
标题 :Esters of cyclopropane-carboxylic acids related to pyrethric acid, their preparation and use as insecticides
摘要:1. Claims (for the Contracting States : BE, CH, DE, FR, GB, IT, LI, LU, NL, SE) In all possible isomeric forms, or in the form of a mixture of isomers, the compounds with the formula I see diagramm : EP0050534,P45,F2 in which the cyclopropane acid copula is of 1R cis structure and the geometry of the double bond is E and in which R represents either a linear, branched or cyclic alkyl radical, saturated or unsaturated, containing from 1 to 8 carbon atoms, possibly substituted by one or more functional groups, identical or different, or an aryl group containing from 6 to 14 carbon atoms, possibly substituted by one or more functional groups, identical or different, or a heterocyclic radical possibly substituted by one or more functional groups, identical or different, X represents a halogen atom and B represents either a benzyl radical possibly substituted by one or more radicals chosen from the group composed of alkyl radicals including from 1 to 4 carbon atoms, alkenyl radicals including from 2 to 6 carbon atoms, alkenyloxy radicals including from 2 to 6 carbon atoms, alkadienyl radicals including from 4 to 8 carbon atoms, the methylene dioxy radical and halogen atoms, or a see diagramm : EP0050534,P46,F1 group in which the substituent R1 represents a hydrogen atom or a methyl radical and the substituent R2 represents a monocyclic aryl or a -CH2 -C=-CH group and in particular a 5-benzyl-3-furyl methyl group, or a see diagramm : EP0050534,P46,F2 group in which a represents a hydrogen atom or a methyl radical and R3 represents an organic aliphatic radical including from 2 to 6 carbon atoms and one or more carbon-carbon unsaturations and in particular the -CH2 -CH=CH2 , -CH2 -CH=CH-CH3 , -CH2 -CH=CH-CH=CH2 , -CH2 -CH=CH-CH2 -CH3 radical, or a see diagramm : EP0050534,P46,F3 group, in which a represents a hydrogen atom or a methyl radical, R3 retains the same significance as before, each of R'1 and R'2 , identical or different, represents a hydrogen atom, a halogen atom, an alkyl radical including from 1 to 6 carbon atoms, an aryl radical including from 6 to 10 carbon atoms, an alkyloxycarbonyl group including from 2 to 5 carbon atoms, or a cyano group, or a see diagramm : EP0050534,P46,F4 group, in which B' represents an oxygen or sulphur atom, a see diagramm : EP0050534,P46,F5 or -CH2 - group or a sulphoxide group or a sulphone group and R4 represents a hydrogen atom, a -C=-CN radical, a methyl radical, a -CONH2 radical, a -CSNH2 radical or a -C=-CH radical, R5 represents a halogen atom or a methyl radical and n represents a numeral, 0, 1 or 2, and in particular the 3-phenoxybenzyl, alpha-cyano-3-phenoxybenzyl, alpha-ethynyl-3-phenoxybenzyl, 3-benzoylbenzyl, 1-(3-phenoxyphenyl) ethyl or alpha-thioamido-3-phenoxybenzyl group, or a see diagramm : EP0050534,P47,F1 group, or a see diagramm : EP0050534,P47,F2 group, in which the substituents R6 , R7 , R8 , R9 represent a hydrogen atom, a chlorine atom, or a methyl radical and in which S/l symbolises an aromatic ring or an analogous dihydro or tetrahydro ring, or a see diagramm : EP0050534,P47,F3 group or a see diagramm : EP0050534,P47,F4 group, in which R10 represents a hydrogen atom or a CN radical, R12 represents a -CH2 -radical or an oxygen atom, R11 represents a thiazolyl or a thiadiazolyl radical, whose bond with see diagramm : EP0050534,P47,F5 can be found at any one of the available positions, R12 being linked to R11 by the carbon atom contained between the sulphur atom and a nitrogen atom, or a see diagramm : EP0050534,P48,F1 group 1. a see diagramm : EP0050534,P48,F1 group or a see diagramm : EP0050534,P48,F2 group in which R13 represents a hydrogen atom or a CN radical, or a see diagramm : EP0050534,P48,F3 group in which R13 is defined as above, and the benzoyl radical is at position 3 or 4, or a see diagramm : EP0050534,P48,F4 group in which R14 represents a hydrogen atom, a methyl, ethynyl or cyano radical and each of R15 and R16 being different, represents a hydrogen, fluorine or bromine atom, or a see diagramm : EP0050534,P48,F5 group in which R14 is defined as above, each of the R17 'S represents independently an alkyl group containing from 1 to 4 carbon atoms, an alkoxy group containing from 1 to 4 carbon atoms, an alkylthio group containing from 1 to 4 carbon atoms, an alkyl sulphonyl group containing from 1 to 4 carbon atoms, a trifluoromethyl group, a 3,4-methylene dioxy group, or a chloro, fluoro or bromo group, p represents a numeral 0, 1 or 2 and B' represents an oxygen atom or a sulphur atom. 1. Claims (for the Contracting State AT) Process for preparing, in all possible isomeric forms, or in the form of a mixture of isomers, the compounds with the formula I : see diagramm : EP0050534,P52,F3 in which R represents either a linear, branched or cyclic alkyl radical, saturated or unsaturated, containing from 1 to 8 carbon atoms, possibly substituted by one or more functional groups, identical or different, or an aryl group containing from 6 to 14 carbon atoms, possibly substituted by one or more functional groups, identical or different, or a heterocyclic radical possibly substituted by one or more functional groups, identical or different, B represents either a linear, branched or cyclic alkyl radical, saturated or unsaturated, containing from 1 to 18 carbon atoms, or the residue of an alcohol used in the synthesis of esters of the pyrethrinoid series and X represents a halogen atom, the ethylene double bond having the geometry Z or E, characterized in that an acid with the formula II : see diagramm : EP0050534,P52,F4 in which X and R retain the same significance as previously, this acid being in the form of mixtures of E or Z isomers or in the form of an E or Z isomer, the substituted cyclopropane ring being able to be in all its possible sterio-isomeric forms, or in the form of a mixture of stereo-isomers or a functional derivative of this acid, is made to react with an alcohol with the formula III : where B retains the same significance as previously or with a functional derivative of this alcohol, so as to obtain a corresponding compound with the formula I, which if desired, is submitted to the action of a selective cleavage agent of the CO2 R group so as to obtain a compound with the formula IV : see diagramm : EP0050534,P53,F1 in which B retains the same significance as previously, then, this acid with the formula IV or a functional derivative of this acid, is submitted to the action of an alcohol with the formula R-OH in which R retains its previous significance, so as to obtain a corresponding compound with the formula I.

专利号:US-4808749-A
优先权日:1980-10-01
标 题:Cyclopropane carboxylic esters and acids
发明人：MARTEL JACQUES; TESSIER JEAN; TECHE ANDRE
权利人:ROUSSEL UCLAF
摘要:Novel esters in all possible isomeric forms of the formula ##STR1## wherein R is selected from the group consisting of (a) optionally unsaturated alkyl of 1 to 8 carbon atoms and optionally unsaturated cycloalkyl or cycloalkyl-alkyl of 3 to 8 carbon atoms optionally substituted with at least one member of the group consisting of halogen, --OH, --SH, --OR', --SR', --NO 2 , ##STR2## --CN, --SO 3 H, --PO 4 H 2 , ##STR3## --SO 2 AlK 2 , --SO 3 AlK 3 , aryl optionally substituted with at least one member of the group consisting of --OH, alkoxy of 1 to 8 carbon atoms, alkyl of 1 to 8 carbon atoms, halogen, --CF 3 , --OCF 3 , --SCF 3 and ##STR4## R' is alkyl of 1 to 8 carbon atoms, R' and R'' are individually selected from the group consisting of hydrogen and alkyl of 1 to 8 carbon atoms, AlK 1 , AlK 2 and AlK 3 are individually alkyl of 1 to 18 carbon atoms, (b) aryl of 6 to 14 carbon atoms optionally substituted with at least one substitutent selected from the group consisting of --OH, alkoxy of 1 to 8 carbon atoms, alkyl of 1 to 8 carbon atoms, halogen, --OCF 3 , --CF 3 and --SCF 3 and (c) heterocycle optionally substituted with at least one member of the group consisting of --OH, alkoxy of 1 to 8 carbon atoms, alkyl of 1 to 8 carbon atoms, halogen, --CF 3 , --OCF 3 and --SCF 3 , B is selected from the group consisting of optionally unsaturated alkyl of 1 to 18 carbon atoms, optionally unsaturated cycloalkyl of 3 to 18 carbon atoms and the remainder of an alcohol used in synthesis of pyrethrinoid esters, X is halogen and the ethylenic double bond may have Z or E geometry having parasitic activity, especially insecticidal acaricidal and nematocidal activity.

专利号:US-4879302-A
优先权日:1986-10-30
标题 :Certain oximino-cyclopropane carboxylates having insecticidal activity
发明人：TESSIER JEAN; DEMOUTE JEAN-PIERRE; CADIERGUE JOSEPH
权利人:ROUSSEL UCLAF
摘要:All possible stereoisomeric forms and mixtures thereof of a compound of the formula I wherein A is selected from the group consisting of hydrogen, optionally unsaturated alkyl and haloalkyl of 1 to 18 carbon atoms, optionally substituted with aryl or a heterocyclic and optionally interrupted by -O- or -S-, optionally unsaturated cycloalkyl of 3 to 18 carbon atoms, aryl of 6 to 14 carbon atoms and heterocyclic, B is selected from the group consisting of hydrogen, alkyl of 1 to 18 carbon atoms optionally interrupted by -S- or -O- and optionally substituted with at least one member of the group consisting of halogen, -OH, alkoxy of 1 to 8 carbon atoms, -SH, thioalkoxy of 1 to 8 carbon atoms, -NO2 and -CN and R is selected from the group consisting of optionally unsaturated alkyl of 1 to 18 carbon atoms and residue of an alcohol used in the synthesis of pyrethrinoid esters having pesticidal activity.

专利号:US-4569928-A
优先权日:1982-11-02
标题:Anti-parasitic esters
发明人：TESSIER JEAN; TECHE ANDRE; DEMOUTE JEAN-PIERRE
权利人:ROUSSEL UCLAF
摘要:Novel esters in all possible isomeric forms and mixtures thereof of the formula I wherein R is selected from the group consisting of (a) optionally unsaturated alkyl of 1 to 18 carbon atoms and optionally unsaturated cycloalkyl or cycloalkylalkyl of 3 to 8 carbon atoms optionally substituted with at least one member of the group consisting of halogen, -OH, -SH, -OR', -SR', -NO2, +TR -SO2AlK2, -SO3AlK3, aryl optionally substituted with at least one member of the group consisting of -OH, alkoxy of 1 to 8 carbon atoms, alkyl of 1 to 8 carbon atoms, halogen, -CF3, -OCF3, -SCF3 and R' is alkyl of 1 to 8 carbon atoms, R'' and R''' are individually selected from the group consisting of hydrogen and alkyl of 1 to 8 carbon atoms, AlK1, AlK2 and AlK3 are individually alkyl of 1 to 18 carbon atoms (b) aryl of 6 to 14 carbon atoms optionally substituted with at least one substituent selected from the group consisting of -OH, alkoxy of 1 to 8 carbon atoms, alkyl of 1 to 8 carbon atoms, halogen, -OCF3, -CF3 and -SCF3 and (c) heterocycle optionally substituted with at least one member of the group consisting of -OH, alkoxy of 1 to 8 carbon atoms, alkyl of 1 to 8 carbon atoms, halogen, -CF3, -OCF3 and -SCF3, A is selected from the group consisting of optionally unsaturated alkyl of 1 to 18 carbon atoms, optionally unsaturated cycloalkyl of 3 to 18 carbon atoms and the remainder of an alcohol used in synthesis of pyrethrinoid esters, X is halogen and the ethylenic double bond may have Z or E geometry having antiparasitic activity, especially insecticidal, acaricidal and nematocidal activity.

专利号:CN-1115325-C
优先权日:1998-08-05
标题 :Method for synthesis of pyrethrin by catalytic esterification of 4-dimethylaminopyridine

专利号:CN-1218030-A
优先权日:1998-08-05
标题:Method for synthesis of pyrethrin by catalytic esterification of 4-dimethylaminopyridine