71510-51-5Relevant articles and documents
Insect pheromones and their analogs LIX. A new method for the synthesis of components of the sex pheromones of insects of the genus Malacosoma
Kukovinets,Kasradze,Salimova,Odinokov,Galin,Fedorov
, p. 358 - 360 (1999)
A new method has been developed for the synthesis of the main components of the sex pheromones of insects of the Malacasoma genus that is based on the selective transformation of the product of the partial ozonolysis of cyclohexa-1,4-diene - methyl 6-oxohex-4E-enoate.
PROCESS FOR PREPARING A FORMYLALKENYL ALKOXYMETHYL ETHER COMPOUND AND PROCESSES FOR PREPARING CONJUGATED DIENE COMPOUNDS FROM THE SAME
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Paragraph 0189-0194, (2021/10/02)
The present invention provide for preparing a formylalkenyl alkoxymethyl ether compound of the following general formula (2): R3CH2OCH2O(CH2)aCH═CHCHO (2), wherein R3 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group; and “a” represents an integer of 1 to 10, the process comprising: hydrolyzing a dialkoxyalkenyl alkoxymethyl ether compound of the following general formula (1): R3CH2OCH2O(CH2)aCH═CHCH(OR1)(OR2) (1), wherein R1 and R2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R1 and R2 may form together a divalent hydrocarbon group, R1-R2, having 2 to 10 carbon atoms; and R3 and “a” are as defined above, in the presence of an acid while removing an alcohol compound thus generated to form the formylalkenyl alkoxymethyl ether compound (2).
Synthesis of (5Z,7E)-dodecane-5,7-diene-1-alcohol as well as acetate and propionate thereof
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, (2019/03/28)
The invention belongs to the technical field of insect pheromone synthesis, and discloses a new method for synthesizing (5Z,7E)-dodecane-5,7-diene-1-alcohol as well as acetate and propionate thereof.The method takes propynol as an initial raw material to be subjected to coupling with 1-bromobutane to generate 2-heptyne-1-alcohol, triple bond is reduced to be E-type double bond through LiAlH4, 2-heptyne-1-alcohol is oxidized to be olefine aldehyde through PDC, olefine aldehyde reacts with a Wittig reagent (5-ethyoxyl-5-oxopentyl)triphenyl phosphonium bromide to produce (5Z,7E)-dodecane-5,7-dienoic acid ethyl ester which is reduced by LiAlH4 to obtain (5Z,7E)-dodecane-5,7-diene-1-alcohol, (5Z,7E)-dodecane-5,7-diene-1-alcohol reacts with acetyl chloride and propionyl chloride finally to obtain (5Z,7E)-dodecane-5,7-diene-1-alcohol acetate and (5Z,7E)-dodecane-5,7-diene-1-alcohol propionate. The method utilizes LiAlH4 to reduce the triple bond to be the E-type double bond, and utilizes theWittig reaction of the Wittig reagent with the tail end provided with ester group and aldehyde to directly build the Z-type double bond, the synthesis route is simple, convenient and efficient, and the reaction condition is moderate and environmentally friendly.
Efficient synthesis of (5Z,7E)-Dodecadienal, the sex pheromone of the european pine moth dendrolimus pini
T?t?s, ?tefania,Vasian, Iuliana,Gorgan, Monica,T?t?s, Róbert,Lar, Claudia
, p. 315 - 319 (2018/10/20)
Efficient synthesis of (5Z,7E)-dodecadienal, the sex pheromone of European pine moth Dendrolimus pini, was stereoselectively accomplished via Pd- and Fe- catalyzed cross-coupling reactions in the key steps. The very simple and practical method developed herein provides a general synthetic approach to other (Z,E)-diene compounds.
