Method for synthesizing sex pheromone of hyphantria cunea

A technology of a white moth and a synthesis method, which is applied in the field of synthesis of American moth sex pheromone, can solve the problems of side reactions, difficult to control sulfonic acid esterification reaction, inability to obtain a sulfonic acid esterified product, and the like, and achieves enantiomers. The effect of high selectivity and simple reaction

Active Publication Date: 2021-04-16
江苏宁录科技股份有限公司
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  • Abstract
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  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Aiming at the problems existing in the prior art, the technical problem to be solved in the present invention is: using propynyl alcohol as a starting material to synthesize (3Z, 6Z, 9S, 10R)-9,10-epoxy-3,6-20 In the method of one-carbadiene, if trifluoromethanesulfonic anhydride is used to carry out the sulfonate reaction of the key intermediate (2S, 3R)-2,3-epoxy-1-tetradecyl alcohol to generate highly active Subsequent reactions after trifluoromethanesulfonate are prone to various side reactions, making the sulfonate reaction difficult to control, and even unable to obtain sulfonate products

Method used

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  • Method for synthesizing sex pheromone of hyphantria cunea

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Add 0.3568mol of propynyl alcohol, 150mL of dichloromethane, and 0.03568mol of p-toluenesulfonamide into a 250mL single-necked bottle, cool in an ice bath, and slowly drop in 42.02g of dihydropyran. After completion, the reaction was quenched by adding saturated aqueous sodium bicarbonate solution, and the organic phase was extracted with dichloromethane, washed with water, washed with brine, dried over anhydrous sodium sulfate, and purified by column chromatography to obtain compound 2 with a yield of 90%.

Embodiment 2

[0037] The PTSA in Example 1 was replaced by pyridinium p-toluenesulfonate, and other conditions remained unchanged, and the yield of compound 2 was 89%.

[0038] Step (2), the synthesis of compound 3:

Embodiment 3

[0040] Under the protection of argon, add 0.19173mol compound 2 and 250mL dry tetrahydrofuran into a 1000mL three-neck flask, cool to -78°C, add 71mL n-BuLi solution with a concentration of 2.7mol / L dropwise, and stir for half an hour after the dropwise addition , Add 0.1743mol 1-bromoundecane and 40g 1,3-dimethylpropylene urea dropwise in sequence at -78°C. After the dropwise addition is completed, slowly rise to room temperature and stir for 24 hours. Gas chromatography monitors until the end of the reaction, and the reaction is complete Finally, the reaction was quenched by adding saturated ammonium chloride aqueous solution, and the organic phase was extracted with ethyl acetate, washed with water, washed with brine, dried over anhydrous sodium sulfate, and purified by column chromatography to obtain compound 3 with a yield of 80%.

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Abstract

The invention relates to the technical field of hyphantria cunea prevention and treatment, in particular to a synthetic method for synthesizing sex pheromone of hyphantria cunea. According to a traditional method for synthesizing (3Z,6Z,9S,10R)-9,10-epoxy-3,6-heneicosadiene by using propargyl alcohol as a starting material in the traditional technology, various side reactions are liable to occur during a sulfonic acid esterification reaction on a key intermediate (2S,3R)-2,3-epoxy-1-tetradecanol by using trifluoromethanesulfonic anhydride. In order to solve the problems, the (3Z,6Z,9S,10R)-9,10-epoxy-3,6-heneicosadiene is successfully synthesized by taking propargyl alcohol as an initial raw material and taking a Sharpless asymmetric dihydroxylation reaction as a key step without the step of the sulfonic acid esterification reaction on a key intermediate (2S,3R)-2,3-epoxy-1-tetradecanol by trifluoromethanesulfonic anhydride in the preparation process. Therefore, the whole reaction is mild and controllable and few in side reactions, and enantioselectivity is high.

Description

technical field [0001] The invention relates to the technical field of white moth control, in particular to a method for synthesizing sex pheromone of white moth. Background technique [0002] The American white moth is a moth of the family Slightidae and the genus White Moth. It has miscellaneous feeding habits, large reproductive capacity, strong adaptability, and wide transmission route. It is a serious worldwide quarantine pest and can harm more than 200 kinds of forest trees, fruit trees, crops and wild plants. American white moth is distributed in the United States, Canada, Eastern European countries, Japan, North Korea and other countries. It was first discovered in Liaoning Province of my country in 1979, and spread to Beijing, Tianjin, Hebei, Liaoning, Shandong, Shaanxi, Henan and other places, causing astonishing losses to my country's sericulture, fruit industry and urban greening. [0003] Chemical control is the most basic method to control white moth, which i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D303/04C07D301/00
Inventor 陈新王玉波张成芳
Owner 江苏宁录科技股份有限公司
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