Synthesis method for ectropis oblique sex pheromone

A synthesis method and pheromone technology, which are applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, catalytic reactions, etc., can solve the problems of less research on epoxidation reactions, and achieve simple and easy control. , The effect of less by-products and cost reduction

Inactive Publication Date: 2014-06-25
ANHUI AGRICULTURAL UNIVERSITY
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  • Abstract
  • Description
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AI Technical Summary

Problems solved by technology

Heteropoly compound is a cage-like macromolecular compound. For olefins with multiple double bonds and large steric hindrance, the reaction mechanism of which

Method used

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  • Synthesis method for ectropis oblique sex pheromone
  • Synthesis method for ectropis oblique sex pheromone
  • Synthesis method for ectropis oblique sex pheromone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] For the synthetic route map of tea geometrid sex pheromone, please refer to figure 1 , including the following steps:

[0043] Step 1. the synthesis of linoleyl alcohol

[0044] Under stirring and ice-bath conditions, slowly dropwise add 7g of methyl linolenate in 140ml of tetrahydrofuran solution to 2.8g of lithium aluminum tetrahydride in 70ml of tetrahydrofuran suspension, continue stirring at 10°C and monitor the progress of the reaction with a thin-layer plate. After 2 hours, the reaction is complete. Pour the reaction solution into the mixed system of ethyl acetate and anhydrous sodium sulfate, add 1ml of water under stirring conditions, and decompose the excess aluminum tetrahydrogen lithium; after the solution becomes clear, pour the ethyl acetate layer out, and the solvent was spin-dried to obtain linoleyl alcohol, which was directly put into the next reaction. The structural formula of linoleyl alcohol is:

[0045]

[0046] Step 2., the synthesis of lino...

Embodiment 2

[0067] Step 1. the synthesis of linoleyl alcohol

[0068] Under stirring and ice-bath conditions, slowly drop 6.5g of methyl linolenate in 135ml of tetrahydrofuran solution into 2.2g of lithium aluminum hydride in 65ml of tetrahydrofuran suspension, continue stirring at 12°C and monitor the progress of the reaction with a thin-layer plate . After 3 hours, the reaction is complete. Pour the reaction solution into the mixed system of ethyl acetate and anhydrous sodium sulfate, add 2ml of water under stirring conditions, and decompose the excess aluminum tetrahydrogen lithium; after the solution becomes clear, pour the ethyl acetate layer out, and the solvent was spin-dried to obtain linoleyl alcohol, which was directly put into the next reaction.

[0069] Step 2., the synthesis of linoleyl p-toluenesulfonate

[0070] Under stirring and cooling in an ice bath, slowly add 4.5 g of p-toluenesulfonyl chloride in 85 ml of dichloromethane solution dropwise to 5.5 g of linoleyl alcoh...

Embodiment 3

[0076] Step 1. the synthesis of linoleyl alcohol

[0077] Under stirring and ice-bath conditions, slowly dropwise add 7.5g of methyl linolenate in 145ml of tetrahydrofuran solution to 3g of lithium aluminum hydride in 75ml of tetrahydrofuran suspension, continue stirring at 15°C and monitor the progress of the reaction with a thin-layer plate. After 5 hours, the reaction is complete. Pour the reaction solution into the mixed system of ethyl acetate and anhydrous sodium sulfate, add 3ml of water under stirring conditions, and decompose the excess lithium tetrahydrogen aluminum; after the solution becomes clear, pour the ethyl acetate layer out, and the solvent was spin-dried to obtain linoleyl alcohol, which was directly put into the next reaction.

[0078] Step 2., the synthesis of linoleyl p-toluenesulfonate

[0079]Under stirring and cooling in an ice bath, slowly add 5.5 g of p-toluenesulfonyl chloride in 95 ml of dichloromethane solution dropwise to 6.5 g of linoleyl alco...

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Abstract

The invention belongs to the field of organic synthesis, and particularly relates to a synthesis method for ectropis oblique sex pheromone [cis-6,7-epoxy-(z,z)-3,9-octadecadiene]. The ectropis oblique sex pheromone is obtained by oxosynthesizing (z,z,z)-3,6,9-octadecatriene in the presence of a catalyst, namely Keggin type tetrabutylammonium divacant lacunary silicotungsate, wherein the mole ratio of (z,z,z)-3,6,9-octadecatriene to the catalyst to an oxidant is (4.8-5.2):(0.006-0.010):(0.8-1.2), the oxidization reaction temperature is at 40-60DEG C, and the oxidization reaction time is 3-8h. according to the synthesis method for ectropis oblique sex pheromone, the middle purification step can be omitted by taking low-cost linolenate as a starting raw material, the environment pollution can be decreased by adopting the green epoxidation method of hydrogen peroxide, the cost can be lowered, the productivity is improved, and the synthesis method provides a new thought and a new method for the green synthesis of the sex pheromone.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a novel synthesis method of propylene oxide compounds, in particular to a tea geometrid sex pheromone [cis-6,7-epoxy-(z,z)-3, 9-Octadecadiene] synthetic method. Background technique [0002] Tea geometrid (Ectropis oblique hypulina Wehrli), also known as arch worm, measuring inch worm, hanging silkworm, inch stem worm, etc., belongs to Lepidoptera (Lepidoptera) Geometriidae (Geometriidae) Branch ruler moth subfamily (Ennominae), is a tea tree. one of the main pests. The insect is currently mainly distributed in Zhejiang, Jiangsu, Anhui, Jiangxi, Hunan, Hubei and Fujian provinces in China. In a year, the summer and autumn tea seasons are the most harmful. When the outbreak is severe, the branches and stems can be bare, like fire, and sometimes there is no tea to pick, resulting in weak tree vigor, poor cold resistance, easy to be damaged by freezing in winter, and the original ...

Claims

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Application Information

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IPC IPC(8): C07D303/04C07D301/12B01J31/16B01J31/18
CPCB01J31/34B01J2231/72C07D301/12C07D303/04
Inventor 宛晓春郭峰杨云秋
Owner ANHUI AGRICULTURAL UNIVERSITY
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