Preparation methods of insect sex pheromone compound, insect sex pheromone ether compound and insect sex pheromone ester compound
A compound and insect technology applied in the field of insect sex pheromone compounds to achieve high double bond stereoselectivity and high yield
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[0026] The invention provides a method for preparing insect pheromone ether compounds, characterized in that the insect pheromone ether compounds have a structure shown in formula (1) or a structure shown in formula (2), the method Include the following steps:
[0027] (1) In the presence of the first catalyst, under the reaction conditions that the hydroxyl group and the tert-butyl protecting group form ether, the first compound having the structure shown in formula (3), isobutylene and the first organic solvent are contacted, and the solvent is removed to obtain first product;
[0028] (2) Under the condition of preparing Grignard reagent, make the first product, metal magnesium and the second organic solvent contact, obtain the first solution, then in the presence of the second catalyst, under the condition of Grignard coupling reaction, make The first solution is contacted with an ester compound containing a double bond, and the ester compound containing a double bond is a ...
Embodiment 1
[0068] This example is used to illustrate the preparation of insect pheromone ether compounds.
[0069] The reaction equation of the present embodiment is as follows:
[0070]
[0071] Under the protection of dry nitrogen, 285 mL of dry petroleum ether, 146 grams (1.07 mol) of 6-chloro-1-hexanol (Ningbo Yinuo Chemical Co., Ltd.), 28 grams of PC-100 (big Porous cation exchange resin, purchased from Shangyu Puer Resin Co., Ltd., with a total exchange capacity of 4.5Mmol / g). Start stirring, keep the temperature at room temperature 25°C, feed 92 grams (1.64mol) of isobutene gas, keep at room temperature 25°C, finish the reaction after 6 hours, remove the cation exchange resin by filtration, and distill under reduced pressure to remove the solvent. It was proved by infrared, nuclear magnetic and mass spectrometry that the product after desolvation was 6-chlorohexyl tert-butyl ether, and the yield was 98%.
[0072] Under the protection of dry nitrogen, under anhydrous and anaer...
Embodiment 2
[0076] This example is used to illustrate the preparation of insect sex pheromone ester compounds.
[0077] Prepare P1 according to the method described in embodiment 1, then carry out esterification reaction, the reaction equation of described esterification reaction is as follows:
[0078]
[0079] Under the protection of dry nitrogen, add 300 grams of anhydrous diethyl ether, 22.7 grams (0.14mol) of anhydrous ferric chloride, cool down to 0°C, add 238.2 grams (1mol) of 8,10-dodecadienyl tert-butyl 320 grams of P1 of the base ether, keep the reaction temperature not more than 5°C, add 153 grams of acetic anhydride (1.5mol) dropwise at a rate of 5 g / min, after the dropwise addition, react at the reaction temperature for 2.5 hours, add 230 grams of Toluene, washed the organic phase twice with 200 grams of water, separated the organic phase, concentrated to obtain product P2, separated and purified P2 to obtain 215.4 grams of product, which was confirmed to be 8,10-dodecadie...
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