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Synthetic method for American white moth sex pheromone

A technology of white moth and synthetic method, which is applied in the field of synthesis of sex pheromone of white moth, achieves the effects of high yield, reduced cost of raw materials, and low price

Active Publication Date: 2018-01-09
SHANGHAI UDCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] In order to solve the industrialization problem of the synthesis of sex pheromone of American white moth, the present invention provides a method for synthesizing sex pheromone of American white moth. The synthetic method of Chang'e pheromone

Method used

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  • Synthetic method for American white moth sex pheromone
  • Synthetic method for American white moth sex pheromone
  • Synthetic method for American white moth sex pheromone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] A kind of synthetic method of white moth sex pheromone a [(9S, 10R)-9,10-epoxy-(3Z,6Z)-3,6-21 carbadiene], the synthetic route is as follows:

[0048]

[0049] Numerical numbers therein represent specific compounds.

Embodiment 2

[0051] The present embodiment comprises the following steps on the basis of embodiment 1:

[0052] A, the synthesis of compound 6

[0053] Dissolve 2-propargyl alcohol in the solvent, control the reaction temperature at -10°C, add butyllithium dropwise, after the dropwise addition, warm up to room temperature, stir for 20 minutes, cool down to -20°C, add 1-bromoundecyl dropwise alkane, warmed to room temperature, stirred overnight, the reaction was complete, the reaction solution was poured into a mixture of ice and water, separated, the organic phase was washed three times with water, washed once with saturated brine, dried over anhydrous sodium sulfate, and concentrated to obtain compound 6;

[0054] B, the synthesis of compound 7

[0055] Methanol and compound 6 were added into the autoclave, under the action of the catalyst, hydrogen was replaced 3 times, stirred at 3 atm for 2 h, the reaction was complete, the catalyst was filtered off, and concentrated to obtain compoun...

Embodiment 3

[0066] The present embodiment comprises the following steps on the basis of embodiment 1:

[0067] A, the synthesis of compound 6

[0068] Dissolve 2-propargyl alcohol in the solvent, control the reaction temperature at -20°C, add butyllithium dropwise, after the dropwise addition, raise the temperature to room temperature, stir for 40min, cool down to -20°C, add 1-bromoundecyl dropwise alkane, warmed to room temperature, stirred overnight, the reaction was complete, the reaction solution was poured into a mixture of ice and water, separated, the organic phase was washed three times with water, washed once with saturated brine, dried over anhydrous sodium sulfate, and concentrated to obtain compound 6;

[0069] The solvent in the step A is a mixed solvent of 2L tetrahydrofuran and hexamethylphosphoric triamide, and the mixing volume ratio is 4:1.

[0070] B, the synthesis of compound 7

[0071] Add methanol and compound 6 into the autoclave, under the catalysis of framework ...

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Abstract

The invention provides a synthetic method for an American white moth sex pheromone. 2-propargyl alcohol which is cheap and easy to obtain is used as a raw material, the American white moth sex pheromone a (9S,10R)-9,10-epoxy-(3Z,6Z)-3,6-heneicosadiene is synthesized in a high enantioselectivity and high yield, and enantiomer excess e.e. achieves 99% or more. According to the synthetic method for the American white moth sex pheromone, the production process is safer, the costs are low, the selectivity is higher, and the synthetic method is more energy-saving and environmentally friendly.

Description

technical field [0001] The invention relates to a propylene oxide compound, in particular to a method for synthesizing the sex pheromone of the white moth. Background technique [0002] Pheromones (pheromones, transliterated as pheromones), also known as pheromones, are secreted by an individual and detected by other individuals of the same species through olfactory organs (such as accessory olfactory bulbs and vomeronasal organs). A substance that exhibits a change in behaviour, mood, mental or physiological mechanisms. It has a communication function, and almost all animals have proved the existence of pheromones. [0003] The sex pheromone of American white moth has three main components (Z,Z)-3,6-cis-9,10-epoxyheneicosadiene【a】, 9Z, 12Z-18CHO【b】, 9Z, 12Z, 15Z-18CHO [c], there are regional differences in the ratio of the three. For example, the ratio of the three announced by U.S.S.R is 21:1:8, while the ratio announced by U.S. is 27:1:6. Component a is undoubtedly the ...

Claims

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Application Information

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IPC IPC(8): C07B53/00C07D301/19C07D303/04C07D303/14
CPCY02P20/52
Inventor 刘聪张福炤仇志凤陈雅芸孙龙飞李波陈明明
Owner SHANGHAI UDCHEM TECH CO LTD
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