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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
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
【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)。
【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/EtOH to 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.
【关键词】 硫代磷酸酯;
杀虫剂;
立体化学;
拆分;
绝对构型;
【Key words】 Phosphorothioate; Insecticide; Stereochemistry; Resolution; Absolute configuration;
【Key words】 Phosphorothioate; Insecticide; Stereochemistry; Resolution; Absolute configuration;
【基金】 国家自然科学基金
- 【文献出处】 高等学校化学学报 ,CHEMICAL RESEARCH IN CHINESE UNIVERSITIES , 编辑部邮箱 ,1994年09期
- 【分类号】TQ450.1
- 【被引频次】5
- 【下载频次】88