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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
【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 ,1 HNMR及元素分析证明其结构
【Abstract】 Methyl 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.
【Key words】 methyl pyropheophorbide-a; Grignard reaction; dehydration; photodynamic therapy (PDT);
- 【文献出处】 有机化学 ,Chinese Journal of Organic Chemistry , 编辑部邮箱 ,2004年06期
- 【分类号】TQ460
- 【被引频次】3
- 【下载频次】117