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Synthesis method of novel sex pheromone component of hyphantria cunea

A technology of white moth and synthetic method, which is applied in the direction of chemical instruments and methods, botany equipment and methods, biocides, etc., can solve the problems of inability to obtain sulfonated products, difficult to control the reaction, high reactivity, etc., and achieve cost Low, prevent excessive hydrogenation, simple reaction conditions

Inactive Publication Date: 2021-04-13
南京沐森林业科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Through synthesis research, we found that trifluoromethanesulfonic acid anhydride has high reactivity and oxidative properties, and the reactivity of the trifluoromethanesulfonate ester generated by the reaction is also very high, and side reactions such as elimination and substitution are prone to occur; therefore, even The sulfonate is carried out at about -80°C, the reaction is still difficult to control, the yield is only 20%, and even the sulfonate product cannot be obtained

Method used

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  • Synthesis method of novel sex pheromone component of hyphantria cunea
  • Synthesis method of novel sex pheromone component of hyphantria cunea
  • Synthesis method of novel sex pheromone component of hyphantria cunea

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Effect test

Embodiment 1

[0042] Sex pheromone components of American white moth (3Z, 6Z, 9S, 10R)-9, 10-epoxy-3, 6-unicosadiene (I) and (3Z, 6Z, 9S, 10R)-9 , 10-epoxy-1,3, the route of the synthetic method of 6-undecatriene (II) is as follows:

[0043]

[0044] Specific steps include:

[0045]Step 1 Synthesis of compound 2

[0046] Dissolve 2.5 g of compound 1 in 100 ml of ethyl acetate, stir to dissolve, add 3.5 g of triphenylphosphine, stir to dissolve, cool to -5°C with ice salt, add 4.8 g of triphenylphosphine in batches within 40 minutes Carbon bromide; Rise naturally to room temperature reaction, TLC detection reaction finishes, add 450 milliliters of n-hexanes and stir for 40 minutes, suction filtration, filtrate film concentration, residue column chromatography purification (V (ethyl acetate): (n-hexane) = 1:35) to obtain 3 g of compound 2.

[0047] Step 2 synthesis of compound 5

[0048] Dissolve 1.6 g of 1,4-heptadiyne (compound 3) in 100 ml of tetrahydrofuran and hexamethylphosphoram...

Embodiment 2

[0056] The American white moth sex pheromone component (3Z, 6Z, 9S, 10R)-9,10-epoxy-3,6-eicosadiene, (3Z, 6Z, 9S, 10R)-9,10-epoxy-1,3,6-21-decatriene, (9Z, 12Z, 15Z)-octadecatrienal (refer to JiefengHu, Xi aoweiHan, YuYuan, ZhuangzhiShi. Angew.Chem.Int.Ed.2017, 56:13342-13346.) The three components were dissolved in 120 μL of redistilled dichloromethane according to the set mass ratio (25:4:1~12:1.2:1) , prepared a certain concentration of white moth sex pheromone solution, placed in the refrigerator, and stored at -30°C for later use.

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Abstract

The invention belongs to the technical field of chemical production, and particularly relates to a novel method for synthesizing sex pheromone components of hyphantria cunea, and the sex pheromone components of hyphantria cunea comprise I [(3Z, 6Z, 9S, 10R)-9, 10-epoxy-3, 6-heneicosa diene ] and II [ (3Z, 6Z, 9S, 10R) -9, 10-epoxy-1, 3, 6-henesa triene ]. Carbon tetrabromide and triphenylphosphine are used to mildly perform bromination reaction on the key intermediate (2S, 3R) -2, 3-epoxy-1-tetradecanol (compound 1) , and the method is simple, convenient and high in yield; according to the invention,1, 4-heptadiyne and 1-heptene-3, 6-diyne are introduced into related structural fragments, so that the reaction steps are reduced, and the reaction yield is improved; and according to the method, the use of the Lingdeler palladium catalyst is abolished, and the P2-type nickel generated in situ by nickel acetate and sodium borohydride is used as the catalyst, so that the production cost is reduced, excessive hydrogenation of carbon-carbon triple bonds is prevented, the reaction is mild and controllable, and the yield is good.

Description

technical field [0001] The invention relates to the technical field of chemical production, in particular to a method for synthesizing a novel sex pheromone component of the white moth. Background technique [0002] American white moth, also known as American lamp moth, autumn curtain caterpillar, autumn curtain moth, belongs to Lepidoptera, Dilipidae, is a world-renowned quarantine pest, mainly harming fruit trees, street trees and ornamental trees, especially broad-leaved trees. , causing serious harm to garden trees, economic forests, farmland shelterbelts, etc., and has been included in the first batch of invasive alien species in my country. [0003] American white moth is a kind of leaf-eating pest that seriously harms many kinds of plants. Its harmful characteristics are: first, it has miscellaneous feeding habits and can harm many kinds of plants including forest trees, fruit trees, crops, and flowers; second, it has strong reproductive ability. Three generations of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D303/04A01N43/20A01P19/00B01J23/755B01J37/16
CPCA01N43/20B01J23/755B01J37/16C07D303/04
Inventor 冯婷张娓娓龙成林舒杨
Owner 南京沐森林业科技有限公司
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