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Preparation method of chilo suppressalis sex pheromone cis-11-hexadecenal

A technology of hexadecenal and Chipoteria sex pheromone, which is applied in the field of preparation of Chipoteria sex pheromone-cis-11-hexadecenal, can solve the problems of expensive reagents and harsh reaction conditions, and achieve The effect of low price, low reaction cost and short time

Inactive Publication Date: 2020-03-27
JILIN INST OF CHEM TECH
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AI Technical Summary

Problems solved by technology

Such as the harsh conditions of the synthesis reaction, expensive reagents, etc.

Method used

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Embodiment Construction

[0019] The technical solutions in the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some of the embodiments of the present invention, but not all of them. Based on the embodiments of the present invention, all other embodiments obtained by persons of ordinary skill in the art without making creative efforts belong to the protection scope of the present invention.

[0020] The embodiment of the invention discloses a sex pheromone Z The preparation method of -11-hexadecenal, concrete steps are as follows:

[0021] (1) Synthesis of 10-bromo-1-decanol tetrahydropyran

[0022] At room temperature, weigh 17.90 g of 10-bromo-1-decanol and p-0.15 g of toluenesulfonic acid into a round-bottomed flask, add 70 ml of dichloromethane solvent, place in an ice bath, slowly drop 7.60 g of dichloromethane under stirring Hydropyran, rose to room temperature and stirred for 12~16h. After the reaction was comp...

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PUM

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Abstract

The invention discloses a preparation method of chilo suppressalis sex pheromone cis-11-hexadecenal. The preparation method comprises the steps of (1) allowing 10-bromine-1-decanol and dihydropyran react to generate 10-bromine-1-decanol tetrahydropyran in a dichloromethane solution; (2) allowing the 10-bromine-1-decanol tetrahydropyrane obtained in the step (1) and 1-hexyne and n-butyllithium to react in a tetrahydrofuran solvent under the protection of nitrogen to generate 11-hexadecene tetrahydropyrane, and reacting the 11-hexadecene tetrahydropyrane with 1-hexyne and n-butyllithium to generate 11-hexadecene tetrahydropyrane; (3) carrying out a reduction reaction on the 11-hexadecene tetrahydropyran obtained in the step (2) and nickel chloride and sodium borohydride to generate cis-11-hexadecene tetrahydropyran in a methanol solution; (4) in methanol, enabling the cis-11-hexadecene tetrahydropyran obtained in the step (3) to react with p-toluenesulfonic acid to generate cis-11-hexadecenol; and (5) in dichloromethane, carrying out an oxidation reaction on the cis-11-hexadecenol obtained in the step (4) and pyridinium chlorochromate to generate the cis-11-hexadecenal. The method issimple to operate and mild in reaction condition. Medicines and reagents used in the reaction are conventional products, are low in price and are easy to obtain, and the reaction cost is reduced.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, and more specifically relates to a preparation method of the sex pheromone-cis-11-hexadecenal of the stem borer. Background technique [0002] Chiloborer belongs to Lepidoptera, Boreridae. It is the most common and most harmful rice pest in rice fields in China. It is distributed in all rice planting areas in my country and causes continuous damage to rice throughout the growth cycle. Young larvae Harm the leaf sheath, turn the leaf sheath yellow, and cause the sheath to wither; in the tillering stage of rice, the larvae gather in the leaf sheath to form a dead heart seedling; In severe cases, rice yields will be lost by 30%. Among the control methods of Chilo borer, chemical control is the most commonly used method, but chemical pesticides are often highly toxic and highly residual, and long-term use will cause insects to develop resistance. Extensive use of chemical pesticides will da...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/29C07C47/21
CPCC07C45/292C07C29/103C07D309/04C07D309/06C07B2200/09
Inventor 娄大伟刘彬曾瑞昌
Owner JILIN INST OF CHEM TECH
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