53963-06-7Relevant articles and documents
Method for preparation of (7Z,11Z)-Hexadecadienal as major sex pheromone of citrus leafminer, Phyllocnistis citrella
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Paragraph 0070; 0071; 0084; 0085, (2018/06/09)
The present invention relates to a manufacturing method of a sex pheromone of a citrus leaf miner (phyllocnistis citrella) for controlling the citrus leaf miner. More specifically, the present invention relates to a method for manufacturing (7Z, 11Z)-hexadecadienal which is a main component of the sex pheromone of the citrus leaf miner from a cheap starting material with high purity and yield while being efficient, simple and economical. The manufacturing method of (7Z, 11Z)-hexadecadienal displayed by chemical formula 1 comprises a step of manufacturing a compound displayed by chemical formula 3 by making an aldehyde compound displayed by chemical formula 2 react with n-pentyl triphenylphosphonium halide through a Wittig reaction, and performing an oxidation reaction.COPYRIGHT KIPO 2018
An efficient and stereoselective synthesis of insect pheromones by way of nickel-catalyzed Grignard reactions. Syntheses of gossyplure and pheromones of Eudia pavonia and Droxophila melanogaster
Ducoux, Jean-Philippe,Le Menez, Patrick,Kunesch, Nicole,Kunesch, Gerhard,Wenkert, Ernest
, p. 6403 - 6412 (2007/10/02)
Three pheromones, (6Z,11Z)-hexadeca-6,11-dien-1-yl acetate (from Eudia pavonia), (5Z,9Z)-heptacosa-5,9-diene (from Drosophila melanogaster) and gossyplure, have been synthesized each by two consecutive consequences of nickel-assisted Grignard reactions with cyclic enol ethers and preparation of Grignard reagents from the resultant alcohols.
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Bestmann,Zeibig,Vostrowsky
, p. 1039 - 1047 (2007/10/02)
Coupling reactions of lithium compounds, (Z)-carbonyl olefination of phosphonium ylides and 'crossed' Wittig olefination of bisylides are the key reaction steps in the synthesis principle for nonconjugated, bisolefinic Lepidoptera pheromones and structural analogs. Double unsaturated (E,Z)- and (E,E)-1-vinyl halides are converted into the corresponding (E,Z)- and (E,E)-1-vinyl lithium compounds and coupled selectively to (E,Z)- and (E,E)-alkadienols, alkadienals and alkadienyl acetates with different carbon chain length, geometry and relative positions of double bonds. 'Crossed' Wittig reactions of 1,ω-alkylidene bisylides with two different alkanals gives rise to the formation of corresponding (Z,Z)-dienic sex attractants and derivatives. A monounsaturated (E)-1-vinyl iodide is the synthon for the preparation of an (E)-alkenyl bromide which is converted to an (E)-alkenyl phosphonium salt and (Z)-selectively olefinated to (Z,E)-isomers of moth sex pheromones.