高等学校化学学报

高等学校化学学报 ›› 1994, Vol. 15 ›› Issue (9): 1327.

• 论文 • 上一篇    下一篇

手性硫代磷酸及其衍生物的研究(Ⅻ)─杀虫剂O－甲基S－丙基O－苯基硫代磷酸酯光学异构体的合成及其绝对构型

唐除痴, 马缚鹏, 张绵吉, 李真   

  1. 南开大学元素有机化学研究所, 天津, 300071
  • 收稿日期:1993-09-18 修回日期:1994-01-29 出版日期:1994-09-24 发布日期:1994-09-24
  • 通讯作者: 唐除痴,男,55岁,教授.
  • 作者简介:唐除痴,男,55岁,教授.
  • 基金资助:

    国家自然科学基金

Studies on Chiral Thiophosphoric Acids and Their Derivatives(Ⅻ)─Synthesis of the Optical Isomers of Insecticidal O-Methyl O-Phenyl S-Propyl Phosphorothiolate and Their Absolute Configuration

TANG Chu-Chi, MA Fu-Peng, ZHANG Mian-Ji, LI Zhen   

  1. Institute of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071
  • Received:1993-09-18 Revised:1994-01-29 Online:1994-09-24 Published:1994-09-24

PDF (PC)

摘要： 以奎宁和番木鳖碱为拆分试剂,成功地拆分了外消旋的O-甲基O-苯基硫代磷酸2.拆分的酸(+)-2和(-)-2在甲醇钠存在下与溴丙烷反应,分别得到旋光活性的(-)-O-甲基S-丙基O-苯基硫代磷酸酯1和(+)-1.通过化学相关法确定了1的绝对构型为(-)-(S)和(+)-(R).

关键词: 硫代磷酸酯, 杀虫剂, 立体化学, 拆分, 绝对构型

Abstract: acemic O-methyl O-phenyl thiophosphoric acid 2 has been successfully resolved through its quinine and brucine salts in methanol solution by the fractional crystallization method. The optically active acids, ( +)-2 and(-)-2, react with propyl bromide in the presence of EtONa/EtOHto give(-)-O-methyl S-propyl O-phenyl phosphorothiolate 1 and(+)-1, respectively.The absolute configuration of the optically active 1 has been established as(-)-(S)and(+)-( R) by the chemical correlation method.

Key words: Phosphorothioate, Insecticide, Stereochemistry, Resolution, Absolute configuration

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