焦脱镁叶绿酸-a甲酯的E-环格氏反应及其脱氧衍生物的合成  

Grignard Reaction on E-Ring of Methyl Pyropheophorbide-aand the Synthesis of Its Deoxy-derivatives

作　　者：纪建业[1] 王进军[2] 王鲁敏[2] 韩光范[3] 沈荣基[4] 

机构地区：[1]通化师范学院化学系,通化134002 [2]烟台大学应用化学系,烟台264005 [3]华东船舶工业学院材料科学与工程学院,镇江212003 [4]仁济大学

出　　处：《有机化学》2004年第6期663-668,共6页Chinese Journal of Organic Chemistry

基　　金：科技部中韩政府间合作项目 (2 0 0 2 )资助项目

摘　　要：以焦脱镁叶绿酸 a甲酯及其 3 甲酰甲基为起始原料 ,通过与直链烷基溴化镁或者环烷基溴化镁进行格氏反应 ,将13 1 位羰基转化为烷羟基 ,经脱水在E 环形成环外碳碳双键 ,完成单 (双 )烷亚甲基取代的 13 1 脱氧焦脱镁叶绿酸衍生物的合成 ,并且讨论了格氏反应的立体化学 .所合成的新化合物均经UV ,IR ,1Methyl pyropheophorbide a and its derivatives substituted by formylmethyl at 3 position were used as starting material for the synthesis of title compounds. The carbonyl groups at 13 1 position were converted into alkyhydroxy groups by means of Grignard reaction with straight or cyclic alkyl magnesium bromide. The exocyclic carbon carbon double bond was formed by dehydration reaction to give mono(di)alkylmethylenesubstituted 13 1 deoxypyropheophorbide derivatives. The stereochemistry of the Grignard reaction on the E ring was discussed. The structures of all these new compounds were characterized by elemental analysis, UV, IR and 1H NMR spectra.

关 键 词：焦脱镁叶绿酸-α甲酯 E-环格氏反应 脱氧衍生物 合成 光动力疗法 抗癌药物 光敏剂 脱水反应 

分 类 号：TQ460[化学工程—制药化工]