Synthetic method of (Z,Z,E)-7,11,13-hexadecatrienal

A technology of hexadecatrienal and synthesis method, which is applied in the field of citrus leafminer pheromone synthesis, can solve immaturity and other problems, and achieve the effects of sufficient reaction, cost reduction, and easy post-processing

Inactive Publication Date: 2015-08-12
宁波纽康生物技术有限公司
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Problems solved by technology

However, this technology is not mature in China
At present, the sex pheromone control technology of citrus leaf miner in my country is still in the research and development stage

Method used

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  • Synthetic method of (Z,Z,E)-7,11,13-hexadecatrienal
  • Synthetic method of (Z,Z,E)-7,11,13-hexadecatrienal

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[0020]The synthetic method of a kind of (Z, Z, E)-7,11,13-hexadecatrienal provided by the present invention, concrete steps are: take 6-bromo-1-hexanol as starting reactant, by The protection reaction of the hydroxyl group and the lengthening of the carbon chain, the resulting product is then coupled with 1-bromo-3-iodopropane, and heated to form a salt with triphenylphosphine, and the obtained Wittig salt is reacted with trans-2 in the presence of an organic base (Z, Z, E)-7,11,13-hexadecatrienal was synthesized by Wittig reaction of -pentenal, followed by Lindlar catalytic hydrogenation, hydroxyl deprotection and oxidation. Wherein, the molecular structural formula of the present invention (Z, Z, E)-7,11,13-hexadecatrienal is as follows figure 1 Shown, the roadmap of synthetic method of the present invention is as figure 2 shown.

[0021] Synthesis of Compound 2: Under argon protection, 6-bromo-1-hexanol (39.82g, 0.22mol) was dissolved in dried dichloromethane (250mL), an...

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Abstract

The invention relates to an improved synthetic method of (Z,Z,E)-7,11,13-hexadecatrienal, wherein the (Z,Z,E)-7,11,13-hexadecatrienal is an important component in a sex pheromone compound of phyllocnistis citrella. The improved synthetic method is carried out with 6-bromo-1-hexanol as an initial raw material and through a coupled reaction, a Wittig reaction and other reactions to synthesize the (Z,Z,E)-7,11,13-hexadecatrienal. The improved synthetic method is advantaged in that the raw material is low in cost and easy to get, and the reactions are safe and convenient in operations and is short in step periods. The improved synthetic method is high in product yield, is free of environmental pollution and can achieve better economic benefit.

Description

technical field [0001] The invention belongs to the technical field of citrus leaf miner pheromone synthesis, and in particular relates to a method for synthesizing the citrus leaf miner pheromone component (Z, Z, E)-7,11,13-hexadecatrienal. Background technique [0002] Citrus leaf miner belongs to Lepidoptera Lepidopteridae, which is one of the most important pests of citrus. It is distributed in citrus producing areas all over the world, and it is also the most important pest in citrus producing areas in South China. Its larvae sneak into the young leaves and shoots of the plant to feed, and form silvery white circuitous insect passages in the upper and lower epidermis layers, resulting in deformed and curled leaves, which are easy to fall and seriously affect the photosynthesis of the plant. , thereby affecting the growth and fruiting of saplings. The rolled leaves of the plant are often the refuge of pests such as leaf tortrix, so it is very difficult to control. What...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C47/21C07C45/29
CPCC07C29/00C07C29/17C07C45/29C07D309/12C07F9/535C07C33/048C07C33/02C07C47/21
Inventor 杜永均周鑫何月秋
Owner 宁波纽康生物技术有限公司
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