89942-12-1Relevant articles and documents
Preparation method of (E, Z)-2, 4-ethyl decadienoate
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Paragraph 0044; 0045, (2019/05/15)
The invention provides a preparation method of (E, Z)-2, 4-ethyl decadienoate. According to the preparation method, n-hexyl aldehyde is taken as an initial raw material, and three step chemical conversion is adopted to prepare a key intermediate 1-bromo heptene; 1-bromo heptene and ethyl acrylate are subjected to coupling reaction under the catalytic effect of a metal catalyst so as to obtain (E,Z)-2, 4-ethyl decadienoate. According to the preparation method, metal catalytic coupling reaction is adopted to replace a step in the prior art that (E, Z)-2, 4-ethyl decadienoate is prepared throughpreparation of an organic copper lithium reagent, water-free oxygen-free harsh conditions are avoided, operation is simplified, reaction efficiency is increased, generation of waste water and waste salt is reduced greatly, equipment investment is reduced, and the preparation method is convenient for industrialization production.
HIGHLY STEREO- AND REGIOSELECTIVE PALLADIUM-CATALIZED SYNTHESES OF (3E,5Z)-(3E,5E)-,AND (3Z,5E)-1,3,5-UNDECATRIENE
Andreini, Bianca Patrizia,Benetti, Massimiliano,Carpita, Adriano,Rossi, Renzo
, p. 4591 - 4600 (2007/10/02)
(3E,5Z)-1,3,5-Undecatriene (3) having 98.2percent stereoisomeric purity has been prepared by a new and expeditious route involving two selective Pd-catalyzed carbon-carbon bond forming reactions.The key step of this synthesis is a highly diastereoselective Pd-catalyzed cross-coupling reaction between 1-heptynylzinc chloride (11a) and a molar excess of (E)/(Z)-1,2-dibromoethylene (12). Another highly diastereoselective Pd-catalyzed reaction, which involves a cross-coupling between trimethylsilylethynylzinc chloride (15) and molar excesses of stereoisomeric mixtures of 1-bromo-1-alkenes (16), has been used to prepare (E)-1-trimethylsilyl-3-nonen-1-yne (10a), a key intermediate for the synthesis of (3E,5E)- and (3Z,5E)-undecatriene, (4) and (5).Compounds 3 and 4, isolated from the essential oil of Ferula galbaniflua, also occur together with compound 5 in the male attracting oils of seaweeds.These substances have odors highly appreciated in perfumery.