化学学报 ›› 1980, Vol. 38 ›› Issue (6): 610-613. 上一篇    

研究简报

昆虫性信息素顺-9-十四碳烯-1-醇乙酸酯的合成

林国强, 郭广忠   

  1. 中国科学院上海有机化学研究所
  • 收稿日期:1978-12-29 出版日期:1980-11-15 发布日期:2013-06-03

INSECT SEX PHEROMONE SYNTHESIS OF Z-9-TETRADECENYL ACETATE

LIN GUO-QIANG, GUO GUANG-ZHONG   

  1. Shanghai Institute of Organic Chemistry, Academia Sinica
  • Received:1978-12-29 Online:1980-11-15 Published:2013-06-03

顺-9-十四碳烯-1-醇乙酸酯(1)是鳞翅目许多昆虫的性信息素或其组分之一[1]。已报道的化合物1的合成方法是采取C10+C4或C9+C5偶联原则[2]。本文报道另一条合成路线(图1),采取C8+C6原则,以1,8-辛二醇(2)为原料,经过ω-氯代辛醇(3)得2-(8'-氯辛烷-1-氧基)四氢吡喃(4)[2d],卤代物4与己炔-1(5)[3]的锂盐缩合得炔化物6,然后以Lindlar催化剂[4]进行部分氢化,粗产品7无需分离可直接去保护基并乙酞化得产物1,五步的总得率约40%.

The title compound (1),the mayor oompound of insect seg pheromone of summer tortrig moth (Adoxophes orama F.von R.) was synthesized.in 5 steps with a 40% overall yield according to the C8+C6 coupling principle,using 1,8-ootandiol as starting material.Namely,coupling of lithium salt of hexyne-1 with 2-(8*chloroocstyloay-)tetra-hydropyrane gave 2-(9'-tetradeoylogy-) tetrahydropyrane,which was partially hydrogenated in the presence of Lindlar catalyst to form compound 7.Simultaneous deprotection and acetylation of 7 with acetyl chloride and acetic acid afforded the title compound 1.The isomeric purity of compound 1 was about 98% as shown by gas chromatography.The E isomer 9 was also synthesized from 6 by means of sodium-liquid ammonia reduction followed by acetylation.