16695-32-2Relevant articles and documents
Method for synthesizing (E)-7-dodecen-1-ol acetate
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, (2019/01/08)
The invention belongs to the technical field of insect pheromone synthesis, and discloses a novel method for synthesizing (E)-7-dodecen-1-ol acetate. The method comprises the following steps: reactinga starting raw material 6-bromo-1-hexanol with 2,3-dihydropyran to obtain 1-tetrahydropyranyloxy-6-bromohexane, and carrying out a coupling reaction on the 1-tetrahydropyranyloxy-6-bromohexane and 1-hexyne in the presence of n-butyllithium to generate 1-tetrahydropyranyloxy-7-dodecyne; reducing the 1-tetrahydropyranyloxy-7-dodecyne by lithium aluminum hydroxide in diethylene glycol dimethyl etherto obtain (E)-tetrahydropyranyloxy-7-dodecene; and removing tetrahydropyran protecting groups by using p-toluenesulfonic acid to synthesize (E)-7-dodecen-1-ol acetate, and finally reacting the (E)-7-dodecen-1-ol acetate with acetyl chloride to obtain the target product (E)-7-dodecen-1-ol acetate. The method has the advantages of simple synthesis route, mild reaction conditions, and realization ofthe total yield reaching 49%.
Pheromone Evaluation of Four Geometric Isomers of 4,11-Hexadecadienal toward Male Eri-Silk Moths
Tomida, Ichiro,Mayesawa, Tsuneaki
, p. 1962 - 1965 (2007/10/02)
Four geometric isomers of 4,11-hexadecadienal were prepared and their pheromone activities to male eri-silk moths were evaluated by using the fluttering test and electro-antennography.None of these compounds showed any activity in spite of their similar structure to other pheromone mimics and to the natural pheromone.These results suggest that the presence of 6,11-double bonds is essential for pheromone activity.
INSECT SEX PHEROMONES. STEREOSELECTIVE SYNTHESIS OF SEVERAL (Z)- AND (E)-ALKEN-1-OLS, THEIR ACETATES, AND OF (9Z,12E)-9,12-TETRADECADIEN-1-YL ACETATE
Rossi, Renzo,Carpita, Adriano,Gaudenzi, Loretta,Quirici, Maria Grazia
, p. 237 - 246 (2007/10/02)
Several female sex pheromone components produced by moths belonging to the order of Lepidoptera, and potential attractants of Dacus oleae (Diptera:Tripetidae) have been synthesized in high chemical and stereoisomeric purity by improved acetylenic routes involving alkylation of lithium 1-alkyn-1-ides in HMPT, followed by (Z) and (E) highly stereoselective reduction of the derived internal alkynes.Particular care has been paid to optimize the parameters of the reactions used and to evaluate the chemical and isomeric purity of the reaction products.The compounds synthesized include (Z)- and (E)-5-nonen-1-ol, (Z)- and (E)-7-dodecen-1-yl acetate, (Z)- and (E)-7-teradecen-1-yl acetate, (Z)- and (E)-7-nonen-1-ol, (Z)- and (E)-9-tetradecen-1-yl acetate, (Z)- and (E)-10-tetradecen-1-yl acetate, (Z)- and (E)-11-tetradecen-1-yl acetate.Pure (Z)-6-nonen-1-ol, which is an attractant of olive fruit fly, D. oleae, and very probably, a constituent of the sex pheromone of females of this insect, has been prepared by a rather efficient copper-catalyzed reaction between (Z)-3-hexen-1-ylmagnesium bromide and oxetane. (9Z,12E)-9,12-Tetradecadien-1-yl acetate, which is the pheromone of Anagasta kuenniella, Ephestia elutella, Cadra figulella, Spodoptera exigua, S. litura, and a component of the sex pheromones of several other Lepidoptera, has been conveniently prepared by using the copper-catalyzed coupling reaction between (E)-1-chloro-2-butene and 10-tetrahydropyranyloxy-1-decenylmagnesium bromide, followed by acetylation and Z-stereoselective reduction of the derived 1,4-enyne.All syntheses have been conducted on a scale to yield less than 50 mmol of the pure sex pheromone components, but seem adaptable for much larger quantities.
