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叶绿素降解产物的羟(烷)基化及其二氢卟吩衍生物的合成 被引量:5

Hydroxy(alky)lation of Chlorophyllous Degradation Products and Synthesis of Their Chlorin Derivatives
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摘要 以脱镁叶绿酸-a甲酯为起始原料,利用二氢卟吩大环上的富电子区域的化学反应性对其实施结构修饰,通过外接E环α-氢的空气氧化、C(3)-乙烯基的亲电加成、羰基的亲核加成和20-meso-氢的亲电取代反应,在外接E环、C(3)-,C(12)-β-位和20-meso-位上完成了羟基或者羟烷基的引进,新建羟基的氧化和脱水反应进一步转换成碳氧双键或者碳碳双键.所合成的11个未见报道的叶绿素类二氢卟吩衍生物的化学结构均经UV,1H NMR,IR及元素分析得以证实,对相应的化学反应提出了可能的反应机理. Methyl pheophorbide-a was used as a starting material, and its modifications were carried out making use of the chemical reactivities of electron-richous regions on the chlorin macrocycle. The introdustions of hydroxyl groups or hy- droxyalkyl groups at exocyclic E-ring, C(3)(C12)-fl-position and 20-meso-position were accomplished by the allomerizations of a-hydrogen of the exocyclic E-ring, the electrophilic addition of C(3)-vinyl group, the nucleophilic addition of the carbonyl groups and electrophilic substitution at C(20)-position. The newly-formed hydroxyl groups were further converted into car- bon-oxygen double bonds or carbon-carbon double bonds by oxidation and dehydration reactions. The chemical structures of 11 unreported chlorin derivatives were characterized by UV, 1H NMR, IR spectra and elemental analysis. The possible mecha- nisms about corresponding reactions were tentatively proposed.
出处 《有机化学》 SCIE CAS CSCD 北大核心 2013年第3期581-589,共9页 Chinese Journal of Organic Chemistry
基金 国家自然科学基金(No.21272048) 山东省自然科学基金(No.Y2008B49)资助项目~~
关键词 叶绿素-A 脱镁叶绿酸 二氢卟吩 羟(烷基)化 合成 chlorophyll-a pheophorbide chlorin hydroxy(alky)lation synthesis
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