Synthesis method of laspeyresia pomonella sex pheromone

Abstract

The invention relates to a synthesis method of laspeyresi pomonella sex pheromone. The method comprises the steps as follows: (1) methanol is added to methyl sorbate as a raw material, and an intermediate A sorbic alcohol is obtained through 5% palladium-carbon catalytic hydrogenation reduction; (2) the intermediate A sorbitol obtained in (1) and acetic anhydride are subjected to a reaction in ethyl acetate, triethylamine and water to obtain an intermediate B sorbic acetate; (3) 6-chlorohexanol is subjected to a reaction with trimethylchlorosilane in toluene in the presence of ethyl acetate and triethylamine, after the reaction, water is added, stirring and layering are performed, and an intermediate C6-chlorohexanol trimethylsilyl ester is obtained; (4) the intermediate B sorbic acetate and the intermediate C6-chlorohexanol trimethylsilyl ester are subjected to a reaction with sodium sand in a toluene solution, then, water and sulfuric acid are dropwise added, layering and rectification are performed, and a target product E8,E10-dodecadiene-1-ol is obtained. The synthesis method has the advantages as follows: the laspeyresi pomonella sex pheromone is synthesized from available rawmaterials, the reaction route is short, and the selectivity and product yield can be increased.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a method for synthesizing codling moth sex pheromone. Background technique [0002] Insect sex pheromone is a trace chemical substance secreted by a certain sex of an insect, accepted by the receptors of the same opposite sex, and causing the opposite sex to produce a certain reproductive behavior response. In the world, the use of insect sex pheromones to monitor and control crop pests and diseases has become a feasible and widely used pest management technology. [0003] Codling moth (Laspey resia pom onella) belongs to the order Lepidoptera and belongs to the family Toricidae. It has the characteristics of wide adaptability, strong fecundity, serious damage, and difficult control. One of the serious fruit borer pests. At present, the basic control methods for pests in agricultural production mainly rely on chemical pesticides, but the long-term unrestrained use of pesticide...

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Problems solved by technology

[0006] 1. Roelofs et al. (1971) synthesized the sex pheromones E8 and E10-dodecadien-1-ol by using "Wittig reaction to construct alkenes", but the route is too long, the yield is low, and the selectivity after isomerization not good too

[0007] 2. Odinokov et al. (1985) synthesized E8, E10-dodecadien-1-ol by using 1,4,92 decatrienyltrimethylsilane as the starting material for hydroboration / oxidation of olefins, The overall yield is high, but the starting material is relatively difficult to obtain

[0009] The yield is 56%, and the stereoselectivity is better than 96%. The disadvantage is that the starting material is relatively difficult to obtain, and the quality of the intermediate product is difficult to control

[0010] 4. Zhang Tao et al. (2005) used the Schlosser2Wittig reaction to stereoselectively synthesize apple The total yield of sex pheromone of silverfish moth is about 30%, and the content of E and E-isomers can reach 98%. The disadvantage is that (trans-crotonaldehyde) is highly toxic, the raw materials are difficult to obtain, and the yield is low

However, the synthesis process requires low-temperature production, and a large amount of sodium borohydride or potassium is used as a reducing agent. The reduction conditions are harsh and the time is long. The production of copper-lithium catalyst requires absolute anhydrous, otherwise the reaction yield will drop sharply.

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