Abstract:
The present invention relates to a 6-hydroxy-3-hexenyl alkoxymethyl ether compound of the following general formula (1): HOCH2CH2CH=CHCH2CH2OCH2OCH2R1 (1), R1 representing a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group; and also relates to a process for preparing a 3,13-octadecadien-1-ol compound of the following formula (6): CH3(CH2)3CH—CH(CH2)8CH═CHCH2CH2OH (6) from the 6-hydroxy-3-hexenyl alkoxymethyl ether compound (1).
Abstract:
The present invention provides processes for preparing an α-necrodyl compound of the following general formula (3): wherein R2 represents a monovalent hydrocarbon group having 1 to 9 carbon atoms, the process comprising: subjecting a 3, 5, 5-trimethyl-3-cyclopentene compound of the following general formula (1): wherein R2 is as defined above, and X represents a leaving group, to a nucleophilic substitution reaction with a methylating agent of the following general formula (2): wherein M represents Li, MgZ1, ZnZ1, Cu, CuZ1, or CuLiZ1, and Z1 represents a halogen atom or a methyl group, to form the α-necrodyl compound (3). The present invention further provides processes for preparing γ-necrodyl compounds of the following general formula (4): wherein R2 represents a monovalent hydrocarbon group having 1 to 9 carbon atoms, the process comprising: subjecting the α-necrodyl compound (3) thus obtained to a positional isomerization reaction at the double bond to form the γ-necrodyl compound (4).
Abstract:
The present invention provides a process for preparing a dimethylcyclobutane compound of the following general formula (1A), the process comprising reacting a dimethylcyclobutanone compound of the following general formula (2) with a phosphonic ester compound of the following general formula (3) to produce an unsaturated ester compound of the following general formula (4), having a dimethylcyclobutane ring, and subjecting the unsaturated ester compound (4), having a dimethylcyclobutane ring, to a reduction reaction to produce the dimethylcyclobutane compound (1A).
Abstract:
Provided is a simple, selective and efficient method for producing 4-alkyl-3-methylenebutyl carboxylates such as 7-methyl-3-methylene-7-octenyl propionate. More specifically, provided is, for example, a method for producing a 4-alkyl-3-methylenebutyl carboxylate compound, comprising an acyloxylation step of subjecting a 1-(2-haloethyl)cyclopropyl sulfonate compound (1) to acyloxylation to obtain a 1-(2-acyloxyethyl)cyclopropyl sulfonate compound (2), a halogenation step of subjecting the compound (2) to halogenation involving cyclopropyl-allyl rearrangement to obtain a 3-halomethyl-3-butenyl carboxylate compound (3), and a coupling step of subjecting the compound (3) to a coupling reaction with an organometallic reagent (4) to obtain the 4-alkyl-3-methylenebutyl carboxylate compound (5).
Abstract:
Provided is a simple, selective and efficient method for producing 4-alkyl-3-methylenebutyl carboxylates such as 7-methyl-3-methylene-7-octenyl propionate. More specifically provided is a method for producing a 4-alkyl-3-methylenebutyl carboxylate compound, the method comprising a diacyloxylation step of subjecting a 4-halo-2-halomethyl-1-butene compound (6) to diacyloxylation to obtain a 3-acyloxymethyl-3-butenyl carboxylate compound (3), and a coupling step of subjecting the 3-acyloxymethyl-3-butenyl carboxylate compound (3) to a coupling reaction with an organometallic reagent (4) to obtain the 4-alkyl-3-methylenebutyl carboxylate compound (5).
Abstract:
Provided is a simple and efficient method for producing 2-isopropylidene-5-methyl-4-hexenyl butyrate. More specifically, provided is a method for producing 2-isopropylidene-5-methyl-4-hexenyl butyrate, the method including the steps of: isomerizing 2-isopropenyl-5-methyl-4-hexenoic acid ester (1) into 2-isopropylidene-5-methyl-4-hexenoic acid ester (2), reducing thus formed 2-isopropylidene-5-methyl-4-hexenoic acid ester (2) into 2-isopropylidene-5-methyl-4-hexenol (3), and butyrylating thus formed 2-isopropylidene-5-methyl-4-hexenol (3) into 2-isopropylidene-5-methyl-4-hexenyl butyrate (4), wherein R represents a C1-10 hydrocarbon group.
Abstract:
The present invention relates to A process for preparing a conjugated diene compound, the process comprising: subjecting, to an intramolecular sigmatropic rearrangement reaction, a conjugated diene compound (1) of the following general formula (1), wherein Z represents a halogen atom, a methyl group, a hydroxy group, an acetoxy group, a formyl group, or an acetal, and n and m are, independently of each other, integers of 0 to 14, or a conjugated diene compound (2) of the following general formula (2), wherein Z, n, and m are as defined above, to obtain, respectively, a conjugated diene compound (3) of the following general formula (3), wherein Z is as defined above, and n and m are, independently of each other, integers of 0 to 14, with the proviso that m−1 is an integer of zero or more, or a conjugated diene compound (4) of the following general formula (4), wherein Z is as defined above, and n and m are, independently of each other, integers of 0 to 14, with the proviso that n−1 is an integer of zero or more.
Abstract:
The present invention relates to a 6-hydroxy-3-hexenyl alkoxymethyl ether compound of the following general formula (1): HOCH2CH2CH=CHCH2CH2OCH2OCH2R1 (1), R1 representing a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group; and also relates to a process for preparing a 3,13-octadecadien-1-ol compound of the following formula (6): CH3(CH2)3CH=CH(CH2)8CH=CHCH2CH2OH (6) from the 6-hydroxy-3-hexenyl alkoxymethyl ether compound (1).
Abstract:
The present invention provides a process for preparing a diester compound of the following general formula (1), having a dimethylcyclobutane ring, wherein R1 and R2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 10 carbon atoms, the process comprising reacting a dimethylcyclobutanone compound of the following general formula (2), wherein R1 is as defined above, with a phosphonic ester compound of the following general formula (3), wherein R2 and R3 represent, independently of each other, a monovalent hydrocarbon group having 1 to 10 carbon atoms, to produce the diester compound (1), having a dimethylcyclobutane ring.
Abstract:
There are provided methods of efficiently producing compounds that are, for example, sex pheromones of San Jose Scale. For example, there is provided a method for producing a 7-methyl-3-methylene-7-octenyl carboxylate compound (4), the method including the steps of: hydrolyzing a 7-methyl-3-methylene-7-octenal acetal compound (1) to obtain 7-methyl-3-methylene-7-octenal (2); reducing the 7-methyl-3-methylene-7-octenal (2) to obtain 7-methyl-3-methylene-7-octenol (3); and esterifying the 7-methyl-3-methylene-7-octenol (3) to obtain a 7-methyl-3-methylene-7-octenyl carboxylate compound (4).