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Method for synthesizing sex pheromone of anarsia lineatella

A synthetic method, the technology of P. chinensis, applied in chemical instruments and methods, the preparation of organic compounds, the preparation of hydroxyl compounds, etc., can solve the problems of harsh reaction conditions, lengthy reaction routes, and high toxicity of reagents

Inactive Publication Date: 2020-05-08
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Although some achievements have been made in the research on the synthesis of sex pheromones of P. chinensis, there are still problems such as harsh reaction conditions, lengthy reaction routes, and high toxicity of reagents.

Method used

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  • Method for synthesizing sex pheromone of anarsia lineatella

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Synthesis of 5-Decyn-1-ol 2

[0021] Under argon protection, 5-hexyn-1-ol 1 (0.20 g, 2 mmol), HMPA (1 mL, 6 mmol) and tetrahydrofuran (10 mL) were sequentially added into a 50 mL Schlenk tube, and stirred evenly. The temperature of the mixture was lowered to -78°C, and n-butyllithium (1.7mL, 2.4M, 4mmol) was slowly added dropwise. After dropping, the mixture was slowly warmed to -30°C and stirred for 1 h. Then 1-bromobutane 2 (0.27 g, 2 mmol) was slowly added dropwise. After the drop, the reaction solution was slowly warmed up to room temperature, and the stirring reaction was continued for 10 h. After the reaction was completed, saturated ammonium chloride aqueous solution (10 mL) was added dropwise under ice cooling to quench the reaction. The layers were separated, the aqueous phase was extracted with ether (3×10 mL), and the organic phases were combined. The organic phase was washed with water (20 mL) and saturated aqueous sodium chloride solution (20 mL), dried ...

Embodiment 2

[0023] Synthesis of (E)-5-decen-1-ol

[0024] Under argon protection, add lithium aluminum hydride (1.48g, 38.88mmol), diethylene glycol dimethyl ether (40mL) and acetylenic alcohol 3 (0.93g, 6.48mmol) into a 100mL three-necked reaction flask equipped with a reflux condenser , the reaction mixture was heated to reflux, and the stirring reaction was continued for 14h. After the reaction, the reaction mixture was cooled to room temperature. Under cooling in an ice bath, aqueous sodium hydroxide solution (5 mL) was added dropwise to quench the reaction. The reaction mixture was suction filtered through celite, and the filter cake was washed with diethyl ether (500 mL). The filtrate was washed with water (3×100mL) and saturated aqueous sodium chloride solution (2×100mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain light yellow liquid compound (E)-5-decen-1-ol (0.94 g, yield 93%). 1 H NMR (300MHz, CDCl 3 )δ5.42–5.38(m,2H),3.64(t,J=6.5H...

Embodiment 3

[0026] Synthesis of (E)-5-Decen-1-ol Acetate

[0027] Under argon protection, (E)-5-decen-1-ol (0.90 g, 5.75 mmol), dichloromethane (15 mL) and triethylamine (3.49 g, 34.5 mmol) were added to a 50 mL Schlenk tube, and the Acetic anhydride (1.76 g, 17.25 mmol) was slowly added dropwise with bath cooling. The reaction solution was warmed up to room temperature, and the stirring reaction was continued for 8h. After the reaction was completed, water (10 mL) was added to quench the reaction. The layers were separated, the aqueous phase was extracted with dichloromethane (3×15 mL), and the organic phases were combined. The organic phase was washed with water (3×20 mL) and saturated aqueous sodium chloride (30 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography (petroleum ether / ethyl acetate 80:1) to obtain light yellow liquid compound (E)-5-decen-1-ol acetat...

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Abstract

The invention belongs to the technical field of green pesticide synthesis, and discloses a novel method for synthesizing sex pheromone of anarsia lineatella. The method comprises the following steps:with 5-hexyn-1-ol as a raw material, subjecting 5-hexyn-1-ol and1-bromobutane to a nucleophilic substitution reaction in the presence of n-butyllithium and HMPA to generate 5-decyn-1-ol, then performing reduction via lithium aluminum hydride to obtain (E)-5-decen-1-ol, and finally performing an acetylation reaction to obtain (E)-5-decen-1-ol acetate. According to the invention, a triple bond of alkyne is reduced into an E-type double bond by lithium aluminum hydride, so the method has the advantages of simple synthetic route, mild reaction conditions, good environmental compatibility and the like.

Description

technical field [0001] The invention belongs to the technical field of green pesticide synthesis, and in particular relates to a new method for synthesizing the sex pheromone of A. chinensis. Background technique [0002] Anarsia lineatella Zeller is distributed in eastern and central Asia, central and southern Europe, and North America. It mainly harms various fruit trees such as peach, apricot, apple, pear, persimmon, sand jujube, plum (Bai Jiuwei; Zhao Jianxia; Ma Wenliang Forestry Science 1980, 127-129+156.). The sex pheromones of Prunus moth have the biological activity of attracting male moths (Roelofs, W.; Kochansky, J.; Anthon, E.; Rice, R.; Carde, R. Environ. Entomol. 1975, 4, 580-582.) , can be used for population monitoring (Hart, M.; Takacs, S.; Gries, G.WO2007053926A1), trapping and interfering mating, etc. (Becker, R.; Buschmann, E.; Mackenroth, W.; Schuermann , G.; Seufert, W.; Seppelt, W.; Krieg, W.; Neumann, U. EP0330160A1). The sex pheromone of P. chinen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C69/145
CPCC07C29/17C07C29/32C07C67/08C07C33/042C07C33/025C07C69/145
Inventor 王敏原超楠钟江春孙效熊官聪王李锋边庆花
Owner CHINA AGRI UNIV
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