Hydroxy(alky)lation of Chlorophyllous Degradation Products and Synthesis of Their Chlorin Derivatives

doi:10.6023/cjoc201210053

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (03): 581-589.DOI: 10.6023/cjoc201210053 Previous Articles Next Articles

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叶绿素降解产物的羟(烷)基化及其二氢卟吩衍生物的合成

殷一樊^a, 张千^a, 刘洋^a, 徐希森^a, 祁彩霞^b, 王进军^a,b

a 烟台大学化学化工学院烟台 264005;
b 山东省黄金工程技术研究中心(工业应用) 烟台 264005

收稿日期:2012-10-31 修回日期:2012-12-01 发布日期:2012-12-06
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. 21272048 )和山东省自然科学基金(No. Y2008B49)资助项目.

Hydroxy(alky)lation of Chlorophyllous Degradation Products and Synthesis of Their Chlorin Derivatives

Yin Yifan^a, Zhang Qian^a, Liu Yang^a, Xu Xisen^a, Qi Caixia^b, Wang Jinjun^a,b

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

Received:2012-10-31 Revised:2012-12-01 Published:2012-12-06
Supported by:
Project supported by the National Natural Science Foundations of China (No. 21272048) and the Natural Science Foundation of Shandong Province (No. Y2008B49).

Methyl pheophorbide-a was used as a starting material, and its modifications were carried out making use of the chemical reactivities of electron-richous regions on the chlorin macrocycle. The introdustions of hydroxyl groups or hydroxyalkyl groups at exocyclic E-ring, C(3)(C12)-β-position and 20-meso-position were accomplished by the allomerizations of α-hydrogen of the exocyclic E-ring, the electrophilic addition of C(3)-vinyl group, the nucleophilic addition of the carbonyl groups and electrophilic substitution at C(20)-position. The newly-formed hydroxyl groups were further converted into carbon-oxygen double bonds or carbon-carbon double bonds by oxidation and dehydration reactions. The chemical structures of 11 unreported chlorin derivatives were characterized by UV, ¹H NMR, IR spectra and elemental analysis. The possible mechanisms about corresponding reactions were tentatively proposed.

Key words: chlorophyll-a, pheophorbide, chlorin, hydroxy(alky)lation, synthesis

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Yin Yifan, Zhang Qian, Liu Yang, Xu Xisen, Qi Caixia, Wang Jinjun. Hydroxy(alky)lation of Chlorophyllous Degradation Products and Synthesis of Their Chlorin Derivatives[J]. Chin. J. Org. Chem., 2013, 33(03): 581-589.

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[1] (a) Kozyrev, A. N.; Chen, Y.-H.; Goswami, L. N.; Tabaczynski, W. A.; Pandey, P. K. J. Org. Chem. 2006, 71, 1949.
(b) Lash, T. D. J. Porphyrins Phthalocyanines 2011, 15, 1093.
(c) Springer, J. W.; Faries, K. M.; Diers, J. R.; Muthiah, C.; Mass, O.; Kee, H. L.; Kirmaier, C.; Jonathan, S.; Lindsey, J. S.; Bocian, D. F.; Dewey Holten, D. Photochem. Photobiol. 2012, 88, 651.
(d) Wang, J.-J. Chin. J. Org. Chem. 2005, 25, 1353 (in Chinese). (王进军, 有机化学, 2005, 25, 1353.)

[2] (a) Jinadasa, R. G. W.; Hu, X.-K.; Vicente, M. G.; Smith, K. M. J. Med. Chem. 2011, 54, 7464.
(b) Kunieda, M.; Tamiaki, H. J. Org. Chem. 2008, 73, 7686.
(c) Goswami, L. N.; Ethirajan, M.; Dobhal, M. P.; Zhang, M.; Missert, J. R.; Shibata, M.; Kadish, K. M.; Pandey, R. K. J. Org. Chem. 2009, 74, 568.
(d) Wu, J.; Yin, J.-G.; Liu, R.-R.; Yang, Z.; Wang, Z.; Wang, J.-J. Chin. J. Org. Chem. 2012, 32, 149 (in Chinese).
(武进, 殷军港, 刘冉冉, 杨泽, 王振, 王进军, 有机化学, 2012, 32, 149.)

[3] (a) Sasaki, S.; Mizutani, K.; Kunieda, M.; Tamiaki, H. Tetrahedron Lett. 2008, 49, 4113.
(b) Wang, J. J.; Shim, Y. K.; Jiang, G. J.; Imafuku, K. J. Heterocycl. Chem. 2004, 41, 29.

[4] (a) Li, J.-Z.; Wang, J.-J.; Yoon, I.; Cui, B.-C.; Shim, Y. K. Bioorg. Med. Chem. Lett. 2012, 22, 1846.
(b) Wang, J.-J.; Li, J.-Z.; Jakus, J.; Shim, Y. K. J. Porphyrins Phthalocyanines 2012; 16, 123.

[5] 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.)

[6] Wang, J.-J.; Wang, P.; Li, J.-Z.; Judit, J.; Shim, R.-K. Bull. Korean Chem. Soc. 2011, 32, 3473.

[7] Wang, J.-J.; Zhao, Y.; Wu, X.-R.; Han, G.-F.; Shim, R.-K. Chin. J. Org. Chem. 2002, 22, 565 (in Chinese).
(王进军, 赵岩, 邬旭然, 韩光范, 沈荣基, 有机化学, 2002, 22, 565.)

[8] Wu, X.-R.; Liu, C.; Yang, Z.; Yao, N.-N.; Wang, J.-J. Chin. J. Org. Chem. 2012, 32, 632 (in Chinese).
(邬旭然, 刘超, 杨泽, 姚楠楠, 王进军, 有机化学, 2012, 32, 632.)

[9] (a) Zheng, G.; Potter, W. R.; Camacho, S. H.; Missert, J. R.; Wang, G.-C.; Bellnier, D. A.; Henderson, B. W.; Michael, H.; Rodgers, M. A. J.; Dougherty, T. J.; Pandey, R. K. J. Med. Chem. 2001, 44, 1540.
(b) 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, 王进军, 有机化学, 2011, 31, 1653.)

[10] Wang, J.-J.; Han, G.-F.; Wu, X.-R.; Shim, R.-J. Chin. J. Org. Chem. 2005, 25, 101 (in Chinese).
(王进军, 韩光范, 邬旭然, 沈荣基, 有机化学, 2005, 25, 101.)

[11] Smith, K. M.; Gogg, D. A.; Simpson, D. J. J. Am. Chem. Soc. 1985, 107, 4946.
[12] Tamiaki, H. K.; Kouraba, M. Tetrahedron 1997, 53, 10677.

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叶绿素降解产物的羟(烷)基化及其二氢卟吩衍生物的合成

Hydroxy(alky)lation of Chlorophyllous Degradation Products and Synthesis of Their Chlorin Derivatives

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