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Simple synthesis method for sex pheromones of oriental fruit moths

The invention relates to a technology for the sex pheromone and synthesis method of the pear worm, which is applied to chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., and can solve the problems of long route, difficult access to raw materials, and inability to large-scale production.

Inactive Publication Date: 2019-05-24
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] There are still many synthetic methods for the sex pheromone of the pear borer moth, but most of them have disadvantages such as long routes, difficult access to raw materials, and inability to produce on a large scale. Therefore, it is of great significance to explore a simple and easy synthetic method

Method used

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  • Simple synthesis method for sex pheromones of oriental fruit moths

Examples

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Effect test

Embodiment 1

[0024] Synthesis of 8-bromooctanol

[0025] Add 1,8-octanediol (250g, 1.712mol), toluene (1000mL), 48% hydrobromic acid (231mL, 2.054mol, 1.2eq) into a 2L three-necked flask, heat to 110°C and reflux for 30 hours. Additional 48% hydrobromic acid (84mL, 0.753mol, 0.44eq) was added, heated to reflux for 20 hours, and a small amount of raw material remained as detected by GC. Cool to room temperature and dilute with 500mL petroleum ether, separate the hydrobromic acid, and wash the organic phase with saturated sodium bicarbonate (400mL×2) and saturated brine (400mL×2) successively, and dry over anhydrous sodium sulfate. Spin-dried to obtain 318g of 8-bromooctyl alcohol with a yield of 83%, which was directly cast into the next step.

Embodiment 2

[0027] Synthesis of 8-Hydroxyoctyltriphenylphosphine Salt

[0028] Add monobrominated product (318g, 1.424mol), acetonitrile (1000mL), triphenylphosphine (409g, 1.566mol, 1.1eq) into a 2L three-necked flask, heat to 94°C and reflux for 48 hours. After the reaction, cool to room temperature and spin dry acetonitrile. Add 500mL of toluene, heat to reflux until homogeneous and stir for 15min, cool to room temperature, and pour out the upper layer of toluene. Repeat the reflux twice. Spin-dry to obtain 602 g of viscous liquid, namely 8-hydroxyoctyl triphenylphosphine salt, with a yield of 88%.

Embodiment 3

[0030] Synthesis of (Z / E)-8-dodecen-1-ol

[0031] Add anhydrous DMSO (500mL) and 60% NaH (102g, 2.556mol, 2eq) into a dry 2L three-necked round-bottom flask, add a 1L storage ball to the middle mouth for buffering, and open the top of the storage ball upward to discharge hydrogen. Heat to 70°C and stir for 1 hour until there are no bubbles to obtain dimethyl sulfoxide sodium salt, and cool to room temperature under nitrogen protection for later use. Add 8-hydroxyoctyltriphenylphosphine salt (602g, 1.278mol) and 1000mL tetrahydrofuran into a 3L mechanically stirred three-neck flask, add the newly prepared sodium dimethyl sulfoxide dropwise, and stir at room temperature for half an hour. Cool to 0°C in an ice bath, add a solution of n-butyraldehyde (110g, 1.5336mol, 1.2eq) in tetrahydrofuran (200mL), dropwise complete, react at 0°C for half an hour, and stir at room temperature for 1 hour. Saturated ammonium chloride (500 mL) was added to quench, the organic phase was separated...

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Abstract

The invention belongs to the field of chemical synthesis, and particularly relates to a simple synthesis method for sex pheromones of oriental fruit moths. The method includes subjecting 1,8-octandiolas a raw material to unilateral bromination reaction to obtain 8-bromooctanol, reacting the 8-bromooctanol with triphenylphosphine to obtain 8-hydroxyoctyl triphenylphosphonium salt, subjecting the 8-hydroxyoctyl triphenylphosphonium salt and n-butanal to Wittig reaction under the action of an alkali to obtain (Z / E)-8-dodecene-1-alcohol, and performing acetylation under the action of pyridine andacetic anhydride to obtain a target product. The cis-trans ratio of enol obtained after the Wittig reaction ranges from 91.8:8.2 to 92.9:7.1; within the optimal attraction range, and by strictly controlling the amount of the acetic anhydride, the properly proportioned sex pheromones of the oriental fruit moths can be obtained according to a 'one-pot' method.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a simple and convenient synthesis method for the sex pheromone of the lepidoptera pest Pear borer. Background technique [0002] The small pear borer belongs to Lepidoptera, Torricidae, is a worldwide fruit tree pests, also known as pear fruit borer, oriental fruit moth, referred to as pear small, mainly harms pears, apples, peaches, hawthorns, apricots, cherries Waiting for fruit trees. In the 1960s, the main components of the sex pheromone of the pear borer were identified as Z-8-dodecen-1-ol acetate, E-8-dodecen-1-ol acetate and Z-8 - the mixture of dodecen-1-ol, after that, the synthesis, biological activity and application of the sex pheromone of pear borer moth have become a research hotspot. A large number of field experiments have shown that the sex pheromone of the pear borer has a killing effect on more than 10 kinds of pests such as the pear borer. The ...

Claims

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Application Information

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IPC IPC(8): C07C69/145C07C67/293
Inventor 何佳怡夏冉吴林盛胡曦文金欣雨陈珂李媛邱琳陈新
Owner CHANGZHOU UNIV
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