Synthetic method of hyphantria cunea sex pheromone components
The invention relates to a technology of American white moth and a synthetic method, which is applied in the directions of organic chemical methods, chemicals for biological control, and pest control, etc., and can solve the problems of inability to obtain sulfonic acid esterification products, difficult reaction control, and high reactivity. Achieve the effect of low cost, prevention of excessive hydrogenation, and simple reaction conditions
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Embodiment 1
[0041] 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:
[0042]
[0043] Specific steps include:
[0044] Step 1 Synthesis of compound 2
[0045] Dissolve 2.3 g of compound 1 in 100 ml of dichloromethane, stir to dissolve, add 3.2 g of triphenylphosphine, stir to dissolve, cool to -5°C with ice salt, add 4 g of tetraphenylphosphine in batches within 1 hour Carbon bromide; rise naturally to room temperature for reaction, TLC detects that the reaction is over, add 400 milliliters of sherwood oil and stir for 30 minutes, filter with suction, concentrate the filtrate film, and purify the residue by column chromatography (V (ethyl acetate): (petroleum ether) = 1:30) to obtain 2.7 g of compound 2 (93% yield).
[0046] Step 2 synthesis of compound 5
[0047]Dissolve 1.4 g of 1,4-heptadiyne (compound 3) in 100 ml of ...
Embodiment 2
[0055] 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-eicosatriene, (9Z,12Z,15Z)-octadecatrienal (refer to Jiefeng Hu, Xiaowei Han, Yu Yuan, ZhuangzhiShi.Angew.Chem.Int.Ed.2017, 56:13342-13346.) The three components were dissolved in 100μL redistilled distilled In methyl chloride, a certain concentration of white moth sex pheromone solution was prepared, placed in the refrigerator, and stored at -20°C for later use.
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