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Fall webworm sex pheromone synthesizing method

A technology of American white moth and synthesis method, which is applied in the fields of botanical equipment and methods, chemicals for biological control, animal repellents, etc., and can solve the problems of complex synthesis of pheromone molecules, low efficiency and low yield, etc. , to achieve the effect of high enantioselectivity, simple operation and separation, and high yield

Inactive Publication Date: 2009-10-07
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Through the above introduction, it is not difficult to see that the synthesis of pheromone molecules IV and V is more complex than III, and the yield is low; the existing method, the whole route can only synthesize a single molecule, and the efficiency is low

Method used

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  • Fall webworm sex pheromone synthesizing method
  • Fall webworm sex pheromone synthesizing method
  • Fall webworm sex pheromone synthesizing method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Step 1 Synthesis of (2S, 3R)-2,3-epoxy-1-14 carbon alcohol (3)

[0044] Under the protection of argon atmosphere, 200 mg of silica gel was mixed with 150 mg of calcium hydride, and 280 mL of dry dichloromethane solvent was injected, followed by 10.9 mL (35.8 mmol) of tetraisopropyltitanium oxide, and stirred at -35°C for 20 min. Slowly inject a solution of L-(+)-diisopropyl tartrate (9825 mg, 41.1 mmol) in dichloromethane (15 mL), and stir at -35°C for 20 min. Slowly inject a solution of (Z)-2-alkyne tetradecyl alcohol 2 (6.6 g, 31.13 mmol) in dichloromethane (15 mL), and stir at -35°C for 20 min. A solution of tert-butanol peroxide (68.49 mmol) in nonane (12.5 mL) was slowly injected, and stirred at -30°C for 3 days. 80 mL of 10% tartaric acid aqueous solution was added to quench the reaction, the temperature was raised slowly, the layers were separated, the aqueous phase was extracted with dichloromethane, and the organic layer was washed three times with saturated b...

Embodiment 2

[0058] Step 1 Synthesis of (2S, 3R)-2,3-epoxy-1-14 carbon alcohol (3)

[0059] Under the protection of argon atmosphere, the activated 3 300mg of molecular sieve powder was injected into 280mL of dry dichloromethane solvent, 1.09mL (3.58mmol) of tetraisopropyltitanium oxide was injected, and stirred at -35°C for 20min. Slowly inject a solution of L-(+)-diisopropyl tartrate (983mg, 4.11mmol) in dichloromethane (5mL) and stir at -35°C for 20min. Slowly inject a solution of (Z)-2-alkyne tetradecyl alcohol 2 (6.6 g, 31.13 mmol) in dichloromethane (15 mL), and stir at -35°C for 20 min. A solution of tert-butanol peroxide (68.49 mmol) in nonane (12.5 mL) was slowly injected, and stirred at -30°C for 3 days. Add 50mL of 10% tartaric acid aqueous solution to quench the reaction, raise the temperature slowly, separate the liquid, and use CH 2 Cl 2After extraction, the organic layer was washed three times with saturated brine (3×20 mL). Drying over anhydrous sodium sulfate, concen...

Embodiment 3

[0073] Step 1 Synthesis of (2S, 3R)-2,3-epoxy-1-14 carbon alcohol (3)

[0074] Under the protection of argon atmosphere, 200 mg of silica gel was mixed with 150 mg of calcium hydride, and 280 mL of dry dichloromethane solvent was injected, followed by 10.9 mL (35.8 mmol) of tetraisopropyltitanium oxide, and stirred at -35°C for 20 min. Slowly inject a solution of L-(+)-diethyl tartrate (8650 mg, 41.1 mmol) in dichloromethane (15 mL), and stir at -35°C for 20 min. Slowly inject a solution of (Z)-2-alkyne tetradecyl alcohol 2 (6.6 g, 31.13 mmol) in dichloromethane (15 mL), and stir at -35°C for 20 min. A solution of tert-butanol peroxide (68.49 mmol) in nonane (12.5 mL) was slowly injected, and stirred at -30°C for 3 days. 80 mL of 10% tartaric acid aqueous solution was added to quench the reaction, the temperature was raised slowly, the layers were separated, the aqueous phase was extracted with dichloromethane, and the organic layer was washed three times with saturated brine...

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Abstract

The invention provides a fall webworm sex pheromone synthesizing method, which relates to an epoxypropane coumpound. The method takes (Z)-2-acetylene tetradecanol synthesized by cheap and easy obtained 2-propargyl alcohol as raw materials, to synthesize fall webworm sex pheromone 3 [(9S, 10R) -9,10 - epoxy - (3Z, 6Z) -3,6-heneidecadienol] and 4 [(9S, 10R) -9,10 - epoxy - (3Z, 6Z) -1,3 ,6-heneidecatrienol] with high efficiency, high enantioselectivity and high yield. Step 6, 25% of the total yield is synthesized into (9S, 10R) -3; 6-step, 21% of the total yield is synthesized into (9S, 10R)-4; and the antipode excess e. e is more than 99%. The separation of the various steps of the invention is simple; the used reagent are all common reagents, cheap and easy to get; the invention has high yield and a shorter route, and is suitable for requirement o f the industrial production.

Description

technical field [0001] The present invention relates to a kind of propylene oxide compound, especially one end is a saturated carbon chain, one end is the synthesis method of an unsaturated carbon chain propylene oxide compound, especially a kind of synthetic white moth sex pheromone III [(9S, 10R) -9,10-epoxy-(3Z,6Z)-3,6-21 carbadiene] and IV [(9S,10R)-9,10-epoxy-(3Z,6Z)-1,3,6 -21 carbatriene] method. Background technique [0002] The American white moth, also known as the autumn curtain caterpillar, is a worldwide quarantine pest, mainly harming fruit trees, street trees, ornamental trees and other broad leaves and crops. This worm originates in North America, and it was introduced into my country in 1979, bringing huge harm to my country's agriculture, forestry production and urban afforestation (1, Ni Jing, Bai Guoyi, Cao Lin, Zhang Fangli; American white moth sex pheromone synthesis research Exploration; chemical propellants and polymer materials; 2002, 6, 14-16), and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D303/04C07D301/19C07D301/00A01N43/20A01P19/00
Inventor 黄培强杜宇郑剑峰江丽娇黄桃吴少锋
Owner XIAMEN UNIV
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