3-位环庚烷(酰)基取代的焦脱镁叶绿酸-a甲酯的合成  

Synthesis of Methyl Pyropheophorbide-a with Cycloheptyl(acyl) Group at 3-Position

作　　者：王进军[1] 刘万卉[2] 韩光范 沈荣基[4] 

机构地区：[1]烟台大学应用化学系,烟台264005 [2]烟台大学药学院,烟台264005 [3]华中船舶工业学院材料与工程学院,镇江212003 [4]仁济大学纳米工程学院

出　　处：《有机化学》2005年第1期65-70,共6页Chinese Journal of Organic Chemistry

基　　金：国家科技部中韩政府间合作研究(2002);山东省技术创新重点(No. 200391006008)资助项目.

摘　　要：以焦脱镁叶绿酸-a 甲酯(MPP-a)为起始原料, 在对其 E-环羰基进行保护的前提下, 经焦脱镁叶绿酸-d 甲酯与环庚基溴化镁进行 Grignard 反应; 所生成新的卟吩仲醇再经脱保护、脱水和氧化等诸多反应, 将 3-位仲羟基转化成碳碳双键和羰基, 其碳氧双键再行 Grignard 反应并脱水成烯, 完成一系列未见报道的 3-位环庚基取代的焦脱镁叶绿酸-a 甲酯衍生物的合成. 其化学结构均经 UV, IR, H NMR 及元素分析予以证实.Methyl pyropheophorbide-a (MPP-a) was used as starting material. The carbonyl group on E-ring of methyl pyropheophorbide-d was protected and the Grignard reaction with cycloheptyl magnesium bromide was performed. The sec-alcohol obtained from Grignard reaction was subjected to deprotection, dehydration, oxidation and other more reaction for converting hydroxyl group at 3-position into carbon-carbon double bond and carbonyl group. The Grignard reaction of the carbon-oxygen double bond and following dehydration were carried out to form olefin. The synthesis of a series of new methyl pyropheophorbide-a substituted by cycloheptyl. group at 3-position was completed. The structures of the compounds were characterized by elemental analysis, UV, IR and H-1 NMR spectra.

关 键 词：甲酯 取代 起始原料 合成 羰基 双键 仲醇 脱镁叶绿酸 反应 IR 

分 类 号：TQ463[化学工程—制药化工]