小菜蛾性信息素的合成SynthesisoftheSexPheromoneofPlutella.PDF

2011 年第 31 卷 有 机 化 学 Vol. 31, 2011 第 12 期, 2126～2130 Chinese Journal of Organic Chemistry No. 12, 2126～2130 ·研究简报· 小菜蛾性信息素的合成 * 宗广辉 颜世强 梁晓梅 王道全 张建军 ( 中国农业大学理学院 农业部农药化学与应用技术重点开放实验室 北京 100193) 摘要 以十一碳烯醇和碘戊烷为原料, 经过苯甲酰基保护、9-硼双环[3.3.1]-壬烷(9-BBN)硼氢化后氧化、氯铬酸吡啶盐 (PCC)氧化、Wittig 反应、脱苯甲酰基五步反应得到顺-11-十六碳烯-1-醇(Z11-16:OH), 五步反应总收率 53%. 顺-11-十 六碳烯-1-醇经 PCC 氧化或 Ac2O 乙酰化分别得到顺-11-十六碳烯-1-醛(Z11-16:Ald) 、顺-11-十六碳烯-1-醇乙酸酯 (Z11-16:Ac), 目标化合物及主要中间体结构经NMR, IR 和 MS 确证. 合成方法路线短, 操作简便, 收率较文献中的方法 有较大提高. 关键词 小菜蛾; 性信息素; 合成; Wittig 反应 Synthesis of the Sex Pheromone of Plutella xylostella (L.) Zong, Guanghui Yan, Shiqiang Liang, Xiaomei Wang, Daoquan Zhang, Jianjun * (Key Laboratory of Pesticide Chemistry and Application Technology, College of Science, China Agricultural University, Beijing 100193) Abstract The main components of the sex pheromone of Plutella xylostella (L.) were synthesized from 10-undecen-1-ol and iodopentane as starting materials. Firstly, Z11-16:OH was obtained by benzoylation of 10-undecen-1-ol, then hydroboration with 9-borabicyclo[3.3.1]nonane (9-BBN) followed by oxidation, fur- ther oxidation with pyridinium chlorochromate (PCC), and then by Wittig reaction and debenzoylation in a total yield of 53% for 5 steps. Z11-16:Ald and Z11-16:Ac were prepared from Z11-16:OH by oxidation or acetylation. Their structures were confirmed by NMR, IR and MS techniques. This is a good method with the advantages of