Synthesis of E/Z-131-Ketoxime Isomers of Methyl Pyropheophorbide-a and Their Alkylation and Acylation

Chinese Journal of Organic Chemistry ›› 2004, Vol. 24 ›› Issue (1): 53-58. Previous Articles Next Articles

E/Z-焦脱镁叶绿酸-a甲酯13¹-酮肟的合成及其烷(酰)基化反应

王进军^*,a, 纪建业^b, 韩光范^c, 沈荣基^d, 森章^e, 初井敏一^e

^a烟台大学应用化学系烟台 264005;
^b通化师范学院化学系通化 134002;
^c华东船舶工业学院材料科学工程系镇江 212003;
^d韩国化学研究所韩国;
^e九州大学机能物质研究所日本

收稿日期:2003-04-18 修回日期:2003-06-13 接受日期:2003-07-18 发布日期:2022-09-21
基金资助:
国家科技部中韩政府间合作项目(2002年度)资助项目.

Synthesis of E/Z-13¹-Ketoxime Isomers of Methyl Pyropheophorbide-a and Their Alkylation and Acylation

WANG Jin-Jun^*,a, JI Jian-Ye^b, HAN Guang-Fan^c, SHIM Young Key^d, Mori Akiro^e, Hatsui Toshihide^e

^aDepartment of Applied Chemistry, Yantai University, Yantai 264005;
^bDepartment of Chemistry, Tonghua Teachers College, Tonghua 134002;
^cSchool of Material Science and Engineering, East China Shipbuilding Institute, Zhenjiang 212003;
^dKorea Research Institute of Chemical Technology, Taejon, Korea;
^eInstitute of Advanced Material Study, Kyushu University, Japan

Received:2003-04-18 Revised:2003-06-13 Accepted:2003-07-18 Published:2022-09-21
Contact: *E-mail: wjj1955@163.com

Abstract

Methyl pyropheophorbide-a (MPP-a) was used as starting material for the synthesis of new chlorin compounds. The Z/E-ketoxime isomers of methyl pyropheophorbide-a were obtained by reaction ofcarbonyl group at 13¹-position with hydroxylamine. The alkylation and acylation of E/Z-ketoximes were carried out by the reaction with alkyl halide andacyl halide to give Z- or E-O-aralkyl ketoxime and O-aroyl (acetyl) ketoxime, respectively. The structures of all these compounds were characterized by elemental analysis, UV, IR, ¹³C NMR and ¹H NMR spectra.

Key words: methyl pyropheophorbide-a, E/Z-13¹-ketoxime of methyl pyropheophorbide-a, alkylation, acylation, photodynamictherapy

Cite this article

WANG Jin-Jun, JI Jian-Ye, HAN Guang-Fan, SHIM Young Key, Mori Akiro, Hatsui Toshihide. Synthesis of E/Z-13¹-Ketoxime Isomers of Methyl Pyropheophorbide-a and Their Alkylation and Acylation[J]. Chinese Journal of Organic Chemistry, 2004, 24(1): 53-58.

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E/Z-焦脱镁叶绿酸-a甲酯13¹-酮肟的合成及其烷(酰)基化反应

Synthesis of E/Z-13¹-Ketoxime Isomers of Methyl Pyropheophorbide-a and Their Alkylation and Acylation

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E/Z-焦脱镁叶绿酸-a甲酯131-酮肟的合成及其烷(酰)基化反应