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Synthetic method for attractant component namely cis,trans-5,7-dodecadiene derivative in Dendrolimus sex pheromone

A synthesis method and pheromone technology, which are applied in attracting pests, botany equipment and methods, chemicals for biological control, etc., can solve the problems of low yield, high cost, unfavorable application, etc., and achieve low price, The effect of short reaction steps and ease of mass production

Inactive Publication Date: 2018-12-14
杭州泽旺生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] If the sex pheromone of the pine caterpillar is extracted from nature, the yield is low, and at the same time, the cost is high, which is not conducive to application. Studies have shown that cis, trans-5,7-deca as shown in structures (I)~(III) Dicarbadiene derivatives are the main components of pine caterpillar pheromones. Therefore, it will be of great significance if such substances can be artificially synthesized

Method used

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  • Synthetic method for attractant component namely cis,trans-5,7-dodecadiene derivative in Dendrolimus sex pheromone
  • Synthetic method for attractant component namely cis,trans-5,7-dodecadiene derivative in Dendrolimus sex pheromone
  • Synthetic method for attractant component namely cis,trans-5,7-dodecadiene derivative in Dendrolimus sex pheromone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Add 5-hexyn-1-alcohol (11.8g, 0.12mol) and 3,4-dihydro-2H-pyran (8.4g, 0.1mol) in reaction flask, then add 1g solid acid catalyst phosphotungstic acid ( h 3 PW 12 o 40 ), 100mL1,2-dichloroethane, reacted at room temperature, after 12 hours of reaction, TLC showed that the reaction was complete. The crude product tetrahydropyran-2-ylynhexyl ether was obtained by filtration and concentration, the product weight was 17.5 g, the yield was 96%, and the GC purity was 95.4%, which was directly carried out to the next step reaction.

Embodiment 2

[0030] Add 5-hexyn-1-ol (11.8g, 0.12mol) and 3,4-dihydro-2H-pyran (8.4g, 0.1mol) to the reaction flask, then add 1g of solid acid catalyst ZSM-5 zeolite , 100mL 1,2-dichloroethane, reacted at room temperature, after 12 hours of reaction, TLC showed that the reaction was complete. After filtration and concentration, the crude product tetrahydropyran-2-ylynhexyl ether was obtained, with a product weight of 17.2 g and a GC purity of 81.2%.

Embodiment 3

[0032] Add tetrahydropyran-2-ylynhexyl ether (18.2 g, 0.1 mol) obtained according to the method of Example 1 into the reaction flask, vacuumize, fill with nitrogen three times, then add 50 mL of dry tetrahydrofuran, stir to dissolve, and cool to -20°C, then a solution of n-butyllithium in pentane (2.5M, 80 mL, 0.2 mol) was added dropwise, and stirring was continued for half an hour. Add hexanal (11g, 0.11mol) tetrahydrofuran (50mL) dropwise to the reaction solution. After the dropwise addition, react at -20°C for two hours, then stir at room temperature for 12 hours. TLC shows that the reaction is complete. The aqueous solution of saturated ammonium chloride was added dropwise to quench, then ethyl acetate was added for extraction, washed twice with saline, and the organic phase was dried with anhydrous magnesium sulfate, filtered, solvent removed, and rectified under reduced pressure. The condensation intermediate was obtained, the product weight was 25.9 g, the yield was 91....

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Abstract

The invention discloses a synthetic method for an attractant component namely a cis,trans-5,7-dodecadiene derivative in Dendrolimus sex pheromone. With the synthetic method provided by the invention,5-hexyne-1-ol and 3, 4-dihydro-2H-pyran used as starting materials are successively subjected to an addition reaction, a condensation reaction, an elimination reaction, a hydrogenation reaction, a deprotection reaction and a derivatization reaction to obtain the cis,trans-5,7-dodecadiene derivative. The synthetic method provided by the invention has the advantages of short route, high reaction yield in each step, simple operation and convenience in mass production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for synthesizing cis, trans-5,7-dodecadiene derivatives as an attractant component in pine caterpillar sex pheromone. Background technique [0002] Pine caterpillar Dendrolimus is the collective name for the insects of the genus Pine caterpillar in the order Lepidoptera. Also known as caterpillar, fire caterpillar, called pine silkworm in ancient times, there are more than 30 species in total, and 27 species are distributed in my country, which is the country with the most abundant species of pine caterpillar. Pine caterpillars can cause food damage to important tree species such as pine, cypress, and fir. The earliest record in China can be found in the "Longchuan County Chronicle" in Guangdong in 1530: "In the ninth year of Jiajing in the Ming Dynasty, severe droughts occurred year after year. The hair was black, and the pine leaves were exhausted and drie...

Claims

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Application Information

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IPC IPC(8): C07C47/21C07C45/29C07C69/145C07C67/08C07C43/15C07C41/16C07D309/12C07C33/02C07C29/10A01N35/02A01N37/02A01N31/02A01P19/00
CPCA01N31/02A01N35/02A01N37/02C07B2200/09C07C29/10C07C41/16C07C45/29C07C67/08C07D309/12C07C47/21C07C69/145C07C43/15C07C33/02Y02P20/55
Inventor 戚一文周宏伟罗宗秀
Owner 杭州泽旺生物科技有限公司
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