CAS: 22373-75-7; (S)-4-Hydroxy-3-Methyl-2-(2-Propenyl)-2-Cyclopenten-1-One

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2-but-3-enyl-2,5-dimethoxy-5-methyl-2,5-dihydro-furan 3-hydroxy-8-nonene-2,5-dione 3-acetyl-2-methyl-3-methylsulfanyl-hex-5-enal (RS)4-hydroxy-3-methyl-2-(2-propynyl)cyclopent-2-ene-1-one phthalic acid mono-(3-allyl-2-methyl-4-oxo-cyclopent-2-enyl ester) t-phenyl-cyclopropane-r-carboxylic acid-((Ξ)-3-allyl-2-methyl-4-oxo-cyclopent-2-enyl ester)(+/-)(1Ξ)-2,2-dimethyl-3t-phenyl-cyclopropane-r-carboxylic acid-((Ξ)-3-allyl-2-methyl-4-oxo-cyclopent-2-enyl ester) t-(4-chloro-phenyl)-2,2-dimethyl-cyclopropane-r-carboxylic acid-((Ξ)-3-allyl-2-methyl-4-oxo-cyclopent-2-enyl ester)(+/-)(1Ξ)-3t-(4-chloro-phenyl)-2,2-dimethyl-cyclopropane-r-carboxylic acid-((Ξ)-3-allyl-2-methyl-4-oxo-cyclopent-2-enyl ester) RS)-trans-chrysanthemumic acid-((RS)-3-allyl-2-methyl-4-oxo-cyclopent-2-enyl ester)(1RS)-trans-chrysanthemumic acid-((RS)-3-allyl-2-methyl-4-oxo-cyclopent-2-enyl ester)

📜在 Barium Dihydroxide体系中,用 甲醇 用作溶剂,化学反应生成S-烯丙醇酮
参考文献:New Synthesis Of Rethrolones
标题:New Synthesis Of Rethrolones
摘要:
Doi:10.1021/ja00746A053

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-9487471-B1
优先权日:2014-04-14
标题 :Synthesis of pyrethroids and pyrethroid-containing compositions
发明人：COELHO PEDRO; MEINHOLD PETER; CHEN MIKE M Y
权利人:PROVIVI INC
摘要:The present invention provides methods for synthesizing pyrethroid compounds. The methods include forming a first reaction comprising an olefin and an allethrolone-type unsaturated alcohol under conditions sufficient to form a metathesis product and converting the metathesis product to the pyrethroid. Methods of the invention can be used to prepare compounds including pyrethrin I, cinerin I, jasmolin I, pyrethrin II, cinerin II, and jasmolin II as well as other synthetic pyrethroid compounds. Insecticidal compositions and methods for controlling insects are also described.

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:SU-1713436-A3
优先权日:1976-09-10
标题 :Method for the synthesis of optically active ester of cyclopropane carboxylic acid and alletrolone with s-configuration

专利号:US-4537897-A
优先权日:1982-09-29
标 题 :3-(1,2-Propadienyl)-cyclopropane-carboxylates
发明人：TESSIER JEAN; DEMOUTE JEAN-PIERRE; CADIERGUE JOSEPH
权利人:ROUSSEL UCLAF
摘要:Novel 3-(1,2-propadienyl)-cyclopropane-carboxylates of the formula I wherein R is alcohol used in pyrethrinoid synthesis, X and Y are both hydrogen or individually halogen or X is hydrogen or halogen and Y is alkyl of 1 to 18 carbon atoms or halogen or X is hydrogen or halogen or alkyl of 1 to 18 carbon atoms and Y is -COOR' or -CN or R' is alkyl of 1 to 18 carbon atoms, R2 and R3 are individually hydrogen or alkyl of 1 to 18 carbon atoms or R2 and R3 together with the nitrogen atom form a heterocycle having pesticidal properties.