Synthesis method of (7Z,11Z,13E)-hexadecatrienal

A technology of hexadecatrienal and hexadecatriene, which is applied in the field of chemical synthesis of hexadecatrienal, the main component of sex pheromone of citrus leafminer moth, to reduce synthesis cost, high stereoselectivity, Effect of High Isomeric Purity

Inactive Publication Date: 2012-11-28
昆明博鸿科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The United States and other countries have used citrus leaf miner sex pheromones for insect population density monitoring, mass trapping and mating interference to prevent and control pests, and achieved good results; while my country's citrus leaf miner sex pheromone control technology is currently in the research and development stage

Method used

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  • Synthesis method of (7Z,11Z,13E)-hexadecatrienal
  • Synthesis method of (7Z,11Z,13E)-hexadecatrienal
  • Synthesis method of (7Z,11Z,13E)-hexadecatrienal

Examples

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Embodiment 1

[0020] Example 1 6-hepten-1-ol ( 4 ) Preparation: 4-bromo-1-butanol (15.3 g, 0.1 mol) was dissolved in 100 ml of anhydrous tetrahydrofuran, and allyl magnesium chloride (0.25 mol, 250ml, 1 M) of anhydrous tetrahydrofuran was added dropwise at 0℃ Solution and lithium tetrachlorocuprate (10 mmol, 0.2 mol / L, 50 ml) in anhydrous tetrahydrofuran solution, continue the reaction for 15 hours, add an appropriate amount of saturated ammonium chloride solution to stop the reaction, distill off the tetrahydrofuran, add ethyl acetate for extraction Three times, the organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated to obtain a crude product, which was distilled under reduced pressure to obtain 6-hepten-1-ol ( 4 ) 9.8 g, yield 86%.

Embodiment 2

[0021] Example 2 7-bromo-1-heptene ( 5 Preparation of ): 6-hepten-1-ol (9.1 g, 80 mmol) was dissolved in 80 ml of dry dichloromethane, phosphorus tribromide (8.13 g, 30 mmol) was added dropwise, and after dropping, continue under ice bath After stirring for 3 hours, add saturated sodium carbonate to neutralize to pH=7-8, separate the organic layer, extract the aqueous layer with dichloromethane once, combine the organic layers, dry over anhydrous sodium sulfate and evaporate the solvent under reduced pressure The crude product was obtained, which was distilled under reduced pressure to obtain 7-bromo-1-heptene ( 5 ) 11.9 g, yield 84%.

Embodiment 3

[0022] Example 3 (6-heptenyl)triphenylphosphonium bromide ( 6 ) Preparation: 7-bromo-1-heptene (11.5 g, 65 mmol) and triphenylphosphine (20.4 g, 78 mmol) were dissolved in 130 ml of toluene, reacted under reflux for 48 hours, and a solid precipitated out, filtered and washed with toluene Twice, the solid was collected and dried under vacuum to obtain 27.1 g of (6-heptenyl)triphenylphosphonium bromide with a yield of 95%.

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Abstract

The present invention relates to a synthesis method of (7Z,11Z,13E)-hexadecatrienal as main constituent of citrus leaf-miner sex pheromone. 7-Bromo-(4Z,6E)-heptadienal and 4-bromo-1-butenol are used as start raw materials, the 4-bromo-1-butenol is coupled with allylmagnesium bromide to obtain 6-hepten-1-ol and then the 6-hepten-1-ol is brominated and salified with triphenylphosphine to obtain 1-bromo-(1E,3Z,7Z,13)-tetradecatetraene, and then the 1-bromo-(1E,3Z,7Z,13)-tetradecatetraen is subjected to Kumada coupling to obtain (1,7Z,11Z,13E)-hexadecatetraene, and then the (1,7Z,11Z,13E)-hexadecatetraene is subjected to hydroboration-oxidation reaction to obtain (7Z,11Z,13E)-hexadecatrienol, and finally the (7Z,11Z,13E)-hexadecatrienol is oxidized into (7Z,11Z,13E)-hexadecatrienal by pyridinium chlorochromate. The synthesis method of (7Z,11Z,13E)-hexadecatrienal has advantages of cheap and easily obtained raw materials, simple synthesis path, mild reaction conditions, high yield, low cost, convenient and safe operation.

Description

technical field [0001] The invention relates to a chemical synthesis method of the main component (7Z, 11Z, 13E)-hexadecatrienal of the sex pheromone of the citrus leaf miner. Background technique [0002] Citrus leafminer ( Phyllocnistis citrella ) belongs to Lepidoptera Lepidopteridae and is the main pest of citrus. It occurs in citrus producing areas all over the world and is an important pest of citrus in South my country. The larvae sneak into the new shoots and young leaves of the plant, and form circuitous insect passages in the disaster layer of the upper and lower epidermis, causing the new shoots and leaves to curl up deformedly, easy to fall off, seriously affecting photosynthesis, and in severe cases, the autumn shoots can be completely damaged. Withered and yellow, affecting the growth and fruiting of young trees. The damaged leaf curls are often refuges and overwintering places for pests such as leaf tortrixes, so it is very difficult to prevent and control t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C47/21C07C45/29
Inventor 陶云海黄飞杨婉秋
Owner 昆明博鸿科技有限公司
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