基于光诱导单电子转移反应的三环异吲哚酮并环肽的合成有机化学.pdfVIP

DOI: 10.6023/cjoc201309023 研究论文 有机化学 Chinese Journal of Organic Chemistry ARTICLE 基于光诱导单电子转移反应的三环异吲哚酮并环肽的合成 董 超 谭广慧 金英学* (哈尔滨师范大学化学化工学院化学系 哈尔滨 150025) 摘要 研究了以邻苯二甲酰亚胺为电子受体, 以肽链为电子给体的新型分子内给受电子体系化合物 1a～1h 在甲醇溶 液中的光反应, 发展了合成三环异吲哚酮并环肽类化合物的方法. 化合物 1a, 1b, 1d～1h 在甲醇溶液中经连续的光诱导 单电子转移(SET)历程生成了三环异吲哚酮并环肽化合物 2a, 2b, 2d～2h. 所有新化合物的结构均经核磁共振谱、高分 辨质谱所确定. 关键词 光反应; 单电子转移(SET); 环肽; 邻苯二甲酰亚胺; 三环异吲哚酮并环肽 Synthesis of Tricyclic Isoindole Cyclic Peptide Based on Photoinduced Single Electron Trasfer Reaction Dong, Chao Tan, Guanghui Jin, Yingxue* (College of Chemistry Chemical Engineering, Harbin Normal University, Harbin 150025) Abstract Exploratory photochemical studies on phthalimido-polypeptides 1a～1h in which phthalimides worked as light absorbance acceptors and polypeptide served as electron donor centers have been conducted, leading to the development of synthetic methodology to construct tricyclic isoindole cyclopeptide mimetics. It was found that irradiation on 1a, 1b, 1d～1h in methanol led to efficient generation of tricyclic isoindole cyclic peptides 2a, 2b, 2d～2h, which may be through sequential single electron transfer (SET) pathway. The structures of new compounds were determined by NMR and HRMS spectroscopy. Keywords photoreaction; single electron transfer (SET); cyclic peptide; phthalimide; tricyclic isoindole cyclic peptide 三环异吲哚酮是许多具有重要的药物活性和生物 许多利用光诱导单电子转移(Single Electron Trans- 活性化合物的基本骨架结构, 例如人体免疫病毒(HIV) fer, SET)机理合成环化物的反应具有产率高、区域选择 抑制剂[1] [2]