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卟吩-f二甲酯合成及其反应机理研究 被引量：9

Reaction Route and Mechanism of Synthesis of Dimethyl Chlorin-f
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摘要 以叶绿素-a为起始原料,经酸性剔除中心金属镁离子得到脱镁叶绿酸-a甲酯.再经过空气氧化和重排反应将其转变为红紫素18-甲酯,在碱性条件下实施开环和脱羧反应,分别得到卟吩p6三甲酯、卟吩-f二甲酯.选择焦脱镁叶绿酸-a甲酯为起始原料,乙醇钠存在条件下进行空气氧化反应,则分别得到15-甲酰基卟吩-f二甲酯和卟吩-f二甲酯.表征了反应产物的化学结构,讨论和提出了可能的反应机理. Chlorophyll-α is used as starting material and converted to methyl pheophorbide-α by removing mag- nesium under acid condition. The purpurin-18 methyl ester is obtained by air oxidation and rearrangement and chlorin p6 trimethyl ester and chlorin-f dimethyl ester are generated by ring-opening and decarboxylation. 15- formyl chlorin-f and chlorin-f are also obtained from pyropheophorbide-α by air-oxidation in the presence of NaOEt. The structures of all these new compounds are characterized by elemental analysis, UV, IR and ^1H NMR spectra. The possible reaction mechanism is discussed.
作者 李付国 赵丽丽 李韵伟 王进军
机构地区 烟台大学药学院
出处 《烟台大学学报（自然科学与工程版）》 CAS 2008年第3期185-190,共6页 Journal of Yantai University(Natural Science and Engineering Edition)
基金 山东省教育厅资助项目(200391006008)
关键词 焦脱镁叶绿酸-α甲酯 卟吩-f二甲酯 叶绿素衍生物 光动力疗癌法(PDT) methyl pyropheophorbide-α chlorin-f dimethyl ester chlorophyll deriveative photodynamictherapy （ PDT ）
分类号 O62 [理学—有机化学]
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参考文献5

  • 1SmithKM, Bisset GM F, Bushell M J. Partial synthesis of optically pure methyl bacteriophophorbides a and d from methyl pheophorbide a [ J]. J Org Chem, 1980, 45: 2218-2224.
  • 2Tamiaki H, Kouraba, M. Synthesis of chlorophyll a homologs by wittig and knoevenagel reactions with methyl pyropheophorbide-d [ J]. Tetrahedron, 1997, 53 (31 ) : 10677 -10689.
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  • 5王进军.叶绿素-a衍生物的化学反应和多取代卟吩(啉)合成的研究进展[J].有机化学,2005,25(11):1353-1371. 被引量：57

二级参考文献5

共引文献56

同被引文献55

  • 1王进军.叶绿素-a衍生物的化学反应和多取代卟吩(啉)合成的研究进展[J].有机化学,2005,25(11):1353-1371. 被引量：57
  • 2荆济荣,李家柱,王进军.叶绿素-a衍生物卟吩环上取代基的变化对其可见光谱的影响[J].烟台大学学报（自然科学与工程版）,2007,20(2):102-107. 被引量：3
  • 3Chen Yihui, Lin Guolin, Pendey R K. Synthesis of bacteriochlorind and their potential untility in photodynamic [J]. Current Org Chem, 2004, 8: 1105-1134.
  • 4Casatano A P, Demidova T N, Hamblin M R. Mechanisms in photodynamic therapy: part one-photosensi-tizers, photochemistry and celluar localization[J]. Photodiag Photodynam Ther, 2004, ( 1 ) : 279-293.
  • 5Nyman E S, Nynninen P H. Research advances in the use of tetrapyrrolic photosensitizers for photodynamic herapy [ J ]. J Photochem Photobiol, 2004, 73 : 1-20.
  • 6Zheng G, William R P, Potter S H, et al. Synthesis, photophsical properties, tumor uptake, and preliminary in vivo photosensitizing efficacy of a homologous series of 3-( 1-alkylxoy)ethyl-3-devinylpurpurion-18 N-alkyl-imides with variable lipophilieity[ J]. J Med Chem, 2001, 44: 1540-1559.
  • 7Saga Y, Miyataka T, Tamiaki H. Self-assemhly of synthetic zinc chlorines in silicate micelle prepared by sol-gel process [ J] , Bioorg Med Chem Lett, 2002, 12:1229-1231.
  • 8SmithKM, BissertGMF, BushellMJ, Partialsynthesis of optically pure methyl bacateriophophorbide a and d from methyl pheophorbide a [ J]. J Org Chem, 1980, 45: 2218 - 2224.
  • 9Chen Yihui, Lin Guolin, Pendey R K. Synthesis of bacteriochlorind and their potential untility in photodynamic [J]. Current Org Chem, 2004, 8: 1105-1134.
  • 10Casatano A P, Demidova T N, Hamblin M R. Mechanisms in photodynamic therapy: part one-photosensi-tizers, photochemistry and celluar localization[ J]. Photodiag Photodynam Ther, 2004, 1 : 279-293.

引证文献9

二级引证文献10

烟台大学学报（自然科学与工程版）
2008年 第3期

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