| 具有叶绿素-a基本碳架的氯代二氢卟吩衍生物的合成 |
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| 引用本文： | 王进军,赵丽丽,李家柱. 具有叶绿素-a基本碳架的氯代二氢卟吩衍生物的合成[J]. 有机化学, 2009, 29(10): 1598-1605 |
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| 作者姓名： | 王进军 赵丽丽 李家柱 |
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| 作者单位： | 烟台大学化学生物理工学院,烟台,264005 |
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| 基金项目： | 山东省自然科学基金，山东省教育厅科技计划，胶体与界面化学教育部重点实验室(山东大学)开放课题 |
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| 摘 要： | 选择脱镁叶绿酸-a甲酯为起始原料, 经过化学结构修饰转换成其他叶绿素-a衍生物. 以过氧化氢/盐酸、N-氯代丁二酰亚胺(NCS)、氯化氢(或者浓盐酸)为氯化剂, 根据3-乙烯基和20-meso-位的不同化学反应活性, 通过亲电加成和亲电取代反应, 在二氢卟吩环上选择性地引进氯原子, 完成8种未见报道的具有叶绿素-a基本碳架的氯代二氢卟吩衍生物的合成. 所合成的新化合物均经UV, IR, 1H NMR及元素分析证明其结构.
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| 关 键 词： | 脱镁叶绿酸-a甲酯 亲电反应 选择性氯代 氯代二氢卟吩 光动力治疗 |
| 收稿时间： | 2009-01-11 |
| 修稿时间： | 2009-03-30 |
Synthesis of Chloro-substituted Chlorin Derivatives withBasic Skeleton of Chlorophyll-a |
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| Affiliation: | (Department of Applied Chemistry, Yantai University, Yantai 264005) |
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| Abstract: | Methyl pheophorbide-a was chosen as a starting material and converted into other chlorophyll-a derivatives by chemical modification. Chlorine atoms were selectively introduced into the chlorin ring based on different reactivity between vinyl group at 3-position and 20-meso position by electrophilic addition and electrophilic substitution using hydrogen peroxide/hydrochloric acid, N-chlorosuccinimide (NCS), hydrogen chloride (or concentrated hydrochloric acid) as chlorinating reagent. Eight new chlorosubstituted chlorin de-rivatives with skeleton of chlorophyll-a were synthesized and their chemical structures were characterized by elemental analysis, UV, IR and 1H NMR spectra. |
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| Keywords: | methyl pyropheophorbide-a electrophilic reaction selective chlorination chlorinated chlorin photodynamic therapy |
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