| 13~2-氧代焦脱镁叶绿酸的E-环修饰及其二氢卟吩类衍生物的合成 |
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| 引用本文： | 邬旭然,刘超,杨泽,姚楠楠,王进军. 13~2-氧代焦脱镁叶绿酸的E-环修饰及其二氢卟吩类衍生物的合成[J]. 有机化学, 2012, 32(3): 632-638 |
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| 作者姓名： | 邬旭然 刘超 杨泽 姚楠楠 王进军 |
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| 作者单位： | 烟台大学化学化工学院 烟台264005 |
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| 基金项目： | 国家自然科学基金(No.20972036);山东省自然科学基(No.Y2008B49);中匈政府间科技合作(No.2008-333-4-32)资助项目~~ |
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| 摘 要： | 以132-氧代焦脱镁叶绿酸-a甲酯为起始原料,碱性条件下的空气氧化和重排反应定量地将其转化成红紫素-18甲酯;在三氟化硼催化下,与苯乙酮的羟醛缩合反应分别给出131-苯甲酰亚甲基取代的二氢卟吩酮和绿卟啉酮;E-环二酮与丙二腈的Knoevenagel反应、与氨基硫脲的缩合反应和与重氮甲烷的重排反应以及与苄基氯化镁的Grignard反应生成一系列具有长波吸收的叶绿素类二氢卟吩衍生物.首次报道的具有叶绿素基本碳架的二氢卟吩衍生物的化学结构均经UV,IR,1H NMR及元素分析得以证实.
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| 关 键 词： | 叶绿素 132-氧代焦脱镁叶绿酸-a甲酯 二氢卟吩 化学修饰 合成 |
Modification for the E-Ring of 132-Oxo-pyropheophorbide-a and Synthesis of Chlorin Derivatives |
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| Wu, Xuran , Liu, Chao , Yang, Ze , Yao, Nannan , Wang, Jinjun. Modification for the E-Ring of 132-Oxo-pyropheophorbide-a and Synthesis of Chlorin Derivatives[J]. Chinese Journal of Organic Chemistry, 2012, 32(3): 632-638 |
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| Authors: | Wu Xuran Liu Chao Yang Ze Yao Nannan Wang Jinjun |
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| Affiliation: | Wu,Xuran Liu,Chao Yang,Ze Yao,Nannan Wang,Jinjun(College of Chemistry and Chemical Engineering,Yantai University,Yantai 264005) |
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| Abstract: | The methyl 132-oxo-pyropheophorbide-a was used as a starting material and converted quantitatively into purpourin-18 by allomerization and rearrangement in the basic condition.Under the catalysis of BF3,the aldol reaction of acetophenone gave 131-phenylacylmethylene-substituted chlorin and keto-rhodin,respectively.The Knoevenagel reaction with malononitrile,condensation with aminothiocarbamide,rearrangement with diazomethane and Grignard reaction with benzyl megnesium bromide afforded a series of chlorins possessing long wavelength absorption.The structures of all the new chlorins with basic skeleton of chlorophyll were characterized by UV,IR,1H NMR spectra and elemental analysis. |
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| Keywords: | chlorophyll methyl 132-oxo-pyropheophorbide-a chlorin chemical modification synthesis |
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