Allomerization of Methyl Pheophorbide-a and Synthesis of Chlorin Derivatives

doi:10.6023/cjoc1202055

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (9): 1700-1707.DOI: 10.6023/cjoc1202055 Previous Articles Next Articles

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焦脱镁叶绿酸-a甲酯的空气氧化反应及其二氢卟吩衍生物的合成

王鲁敏^a, 王朋^a, 刘超^a, 金英学^b, 王进军^a,c

a 烟台大学化学化工学院烟台 264005;
b 哈尔滨师范大学化学化工学院哈尔滨 150025;
c 山东省黄金工程技术研究中心(工业应用) 烟台 264005

收稿日期:2012-02-05 修回日期:2012-05-16 发布日期:2012-03-27
通讯作者: 王进军 E-mail:wjj1955@163.com
基金资助:
国家自然科学基金(No.20972036 )和山东省自然科学基金(No.Y2008B49)资助项目

Allomerization of Methyl Pheophorbide-a and Synthesis of Chlorin Derivatives

Wang Lumin^a, Wang Peng^a, Liu Chao^a, Jin Yingxue^b, Wang Jinjun^a,c

a College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005;
b College of Chemistry and Chemical Engineering, Harbin Normal University, Harbin 150025;
c Shandong Applied Research Centre of Gold Nanotechnology (Au-SDARC), Yantai 264002

Received:2012-02-05 Revised:2012-05-16 Published:2012-03-27
Supported by:
Project supported by the National Natural Science Foundations of China (No.20972036) and the Natural Science Foundation of Shandong Province of China(No.Y2008B49)

The allomerization of methyl pyropheophorbide-a, used as starting material, was carried out under the alkaline condition to separate a series of oxidized and rearranged products at exocyclic E-ring and C-12-methyl group. The same reaction of chlorinated methyl pyropheophorbide-a also came through similar processes. The further oxidations of C-13²-and C-12-oxidized products gave two different results, the former reacted quickly and produced complicated compounds, the latter HH basically HH unchanged under the same condition. The structures of all new chlorin derivatives were characterized by elemental analysis, UV, IR and ¹H NMR spectra. The possible mechanisms about corresponding reactions were tentatively proposed.

Key words: chlorophyll-a, pyropheophorbide, chlorin, allomerization, mechanism

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Wang Lumin, Wang Peng, Liu Chao, Jin Yingxue, Wang Jinjun. Allomerization of Methyl Pheophorbide-a and Synthesis of Chlorin Derivatives[J]. Chin. J. Org. Chem., 2012, 32(9): 1700-1707.

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References

[1] Kozyrev, A. N.; Chen, Y.-H.; Goswami, L. N.; Tabaczynski, W. A.; Pandey, P. K. J. Org. Chem. 2006, 71, 1949.

[2] Hynninen, P. H.; Hyvärinen, K. H. J. Org. Chem. 2002, 67, 4055.

[3] Kunieda, M.; Tamiaki, H. J. Org. Chem. 2008, 73, 7686.

[4] Wang, J.-J. Chin. J. Org. Chem. 2005, 25, 1353 (in Chinese).(王进军, 有机化学, 2005, 25, 353.)

[5] Ethirajan, M.; Joshi, P.; Willian, W. H.; Ohkubo, K.; Fukuzumi, S.; Pandey, R. K. Org. Lett, 2011, 13, 1956.

[6] Goslinski, T.; Piskorz, J. J. Photochem. Photobiol., C 2011, 12, 304.

[7] Wu, J.; Yin, J.-G.; Zhang, Q.; Sun, C.-M.; Li, F.-G.; Pei, W.; Wang, J.-J. Chin. J. Org. Chem. 2011, 31, 1653 (in Chinese).(武进, 殷军港, 张千, 孙传民, 李付国, 裴文, 王进军, 有机化学, 2011, 31, 1653.)

[8] Yin, J.-G.; Wu, X.-R.; Liu, C.-L.; Zhao, L.-L.; Jin, Y.-X.; Wang, J.-J. Chin. J. Org. Chem. 2011, 31, 1870 (in Chinese).(殷军港, 邬旭然, 刘春林, 赵丽丽, 金英学, 王进军, 有机化学, 2011, 31, 1870.)

[9] Wang, J.-J.; Zhang, P.; Wang, P.; Chen, G.-L.; Li, F.-G. Chin. J. Org. Chem. 2010, 30, 1192 (in Chinese).(王进军, 张朋, 王朋, 陈冠龙, 李付国, 有机化学, 2010, 30, 1192.)

[10] Smith, K. M.; Gogg, D. A.; Simpson, D. J. J. Am. Chem. Soc. 1985, 107, 4946.

[11] Zhang, G.; Potter, R. P.; Camacho, S. H.; Missert, J. R.; Wang, G. H.; Bellnier, D. A.; Henderson, B. W.; Rodgers, M. A. J.; Dougherty, T. J.; Pander, R. K. J. Med. Chem, 2001, 44, 1540.

[12] (a) Wang, J.-J.; Zhao, L.-L.; Li, J.-J. Chin. J. Org. Chem. 2009, 29, 1598 (in Chinese).(王进军, 赵丽丽, 李家柱, 有机化学, 2009, 29, 1598.)

(b) Li, J.-Z. M.S. Thesis, Yantai University, Yantai, 2007 (in Chinese).(李家柱, 硕士论文, 烟台大学, 烟台, 2007.)

[13] Juho, H.; Maria, S. M.; Ilkka, K.; Paavo, H. H. J. Org. Chem. 2000, 65, 3700.

[14] Hynninen, P. H.; Kavakka, J. S.; Mesilaakso Tetrahedron Lett. 2005, 46, 1145.

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焦脱镁叶绿酸-a甲酯的空气氧化反应及其二氢卟吩衍生物的合成

Allomerization of Methyl Pheophorbide-a and Synthesis of Chlorin Derivatives

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