35153-20-9Relevant academic research and scientific papers
A facile synthesis of the sex pheromone of Grapholitha molesta
Li, Jiu-Ming,Yong, Jian-Ping,Huang, Feng-Lan,Bai, Shu-Zhen
, p. 103 - 105 (2012)
The sex pheromone of Grapholitha molesta, (Z/E)-8-dodecylen-1-ol acetate, was easily synthesized in an overall yield of 41.5% with 1,8-octanediol as starting material via mono-esterification, PCC oxidation, and Witting reactions. The Z/E ratio is 83:17. Configuration transformation of Z/E 83:17 compound with sodium nitrite and nitric acid resulted in the production of a compound with Z/E 24:76. The products were confirmed by IR, 1H NMR, and MS spectral data.
Improved method for preparing (Z, E)-12-tetradecene-1-alcohol acetate
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Paragraph 0045; 0052; 0053; 0056; 0064; 0065, (2021/03/31)
The invention provides an improved method for preparing (Z, E)-12-tetradecene 1-alcohol acetate, which innovatively introduces a three-solvent system into a solvent system in wittig reaction, increases the solubility of the reagent in the reaction system, lowers the overall freezing point of the solvent, avoids the agglomeration phenomenon at lower temperature in the reaction process under dual actions, and unsmooth reaction stirring and generation of a large number of impurities are avoided, so that the post-treatment difficulty is increased; glacial acetic acid is used for terminating the reaction and replacing previous water-containing dilute acid, condensation of residual aldehydes in the raw materials is controlled, generation of a large number of impurities is avoided, and once a condensation product generates p-triphenylphosphine oxide and a main product enol which are high in solubility and cannot be separated, the aftertreatment difficulty can be greatly enhanced, and the product extraction loss is large; and meanwhile, the reaction can be carried out in a homogeneous state at about 0 DEG C, so that the conversion is thorough, the yield is greatly improved, the post-treatment is simple, the byproduct triphenoxyphosphine is separated out in a granular form, and a large amount of muddy wastes and other solid wastes are avoided.
Synthesis method for sex pheromone of ostriniafurnacalis
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Paragraph 0071; 0080; 0088; 0089; 0092; 0100; 0101; 0104, (2020/05/19)
The invention discloses a synthesis method for a sex pheromone of ostriniafurnacalis, namely a (Z, E)-12-tetradecen-1-ol acetate compound. The synthesis method comprises the following steps: firstly,performing a reaction on 1, 12-dibromododecane and triphenylphosphine to produce omega-bromododecyltriphenylphosphonium bromide, then performing a reaction on the omega-bromododecyltriphenylphosphonium bromide and aldehyde under the action of organic alkali sodium dimethyl sulfoxide to produce Z-main type omega-bromotetradecene, then hydrolyzing by alkali metal hydroxide to obtain Z-main type (Z,E)-12-tetradecen-1-ol, performing an acetylation reaction on the (Z, E)-12-tetradecen-1-ol and acetic anhydride to obtain Z-main type(Z, E)-12-tetradecen-1-ol acetate, and performing an isomer conversion reaction on the Z-main type(Z, E)-12-tetradecen-1-ol acetate and a sodium nitrite and nitric acid solution to obtain E-main type(Z, E)-12-tetradecen-1-ol acetate. With the synthesis method, few side reactions occur in the synthesis process and the product purity is high.
Design, Synthesis, and Biological Evaluation of the Sex Pheromone of the Asian Corn Borer, Ostrinia furnacalis (Guenée)
Lu, Zhengchang,Liu, Wei,Pan, Hongyu,Zhang, Dawei
, (2018/04/12)
A convenient total synthesis of (Z)-12-tetradecenyl acetate (1a) and (E)-12-tetradecenyl acetate (1b), which are the sex pheromones of Ostrinia furnacalis (Guenée), has been achieved. The target mixture molecules, of a cis-to-trans-isomer ratio of 27 to 73, were synthesized in 40% overall yield and through [13C + 1C] synthetic strategy in five steps from commercially available and cheap industrial brassylic acid as key starting material. The electroantennogram (EAG) responses of synthetic sex pheromone to ACB male moths were conducted. The results showed that the target mixture molecules were found to have a good activity and displayed significantly stronger EAG responses ranging from 10 to 1000 μg, and the optimized stimulating dosage of the activity of synthetic sex pheromone to ACB males is 10 μg. Compared with the existing routes, this synthetic approach is operationally simple, good-yielding, and cost-effective, which could serve as a basis for developing the techniques of sex pheromone mass trapping or mating disruption and providing an environmentally benign method to control ACB pests.
A "TUNABLE" STEREOSELECTIVE ALKENE SYNTHESIS BY IODODESILYLATION OF VINYLSILANES
Chan, T. H.,Koumaglo, K.
, p. 883 - 886 (2007/10/02)
The stereoselectivity of iododesilylation of terminal E-vinylsilanes varies with changing amount of Lewis acid.The use of this "tunable" stereoselective reaction was demonstrated by the syntheses of two insect sex pheromones with defined E/Z isomeric rations.
