Transformation for Exocyclic Ring of Pheophorbide and Syn-thesis of Chlorophyllous Degradation Derivatives

doi:10.6023/cjoc201408009

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (5): 1060-1068.DOI: 10.6023/cjoc201408009 Previous Articles Next Articles

ARTICLE

脱镁叶绿酸的外接环转换与芳环取代叶绿素降解衍生物的合成

张善国^a, 李家柱^a, 张朋^a, 祁彩霞^b, 王进军^a,b,c

a 烟台大学化学化工学院烟台 264005;
b 烟台大学文经学院烟台 264005;
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:2014-08-09 修回日期:2014-10-23 发布日期:2015-01-06
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)和山东省黄金工程技术研究中心(2011年度)资助项目.

Transformation for Exocyclic Ring of Pheophorbide and Syn-thesis of Chlorophyllous Degradation Derivatives

Zhang Shanguo^a, Li Jiazhu^a, Zhang Peng^a, Qi Caixia^b, Wang Jinjun^a,b,c

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

Received:2014-08-09 Revised:2014-10-23 Published:2015-01-06
Supported by:
Project supported by the National Natural Science Foundations of China (No.21272048) and the Project of Shandong Applied Reaearch Centre of Gold Nano-technology (2011).

1. Transformation for Exocyclic Ring of Pheophorbide and Syn-thesis of Chlorophyllous Degradation Derivatives.PDF(2822KB)

Abstract

From pheophorbide-a methyl ester, the substituted groups with aromatic ring, which can conjugated with chromophore in different forms, were established at 3-, 12- and 20-position on the chlorin periphery by some classic reactions such as 1,3-dipolar cycloaddition, radical substitution and Wittig olefin-forming. The transformations in the exocyclic ring to other chlorophyllous degradation structures were carried out making use of allomerization, condensation and rearrangement reac-tions. A series of unreported new chlorins were synthesized and their chemical structures were characterized by elemental analysis, UV, IR and ¹H NMR spectra. In the same time the chemical reaction process around the periphery, the conjugated effect about the aromatic substitutes and the varying law about electronic spectra of the macrocyclic molecule were also discussed.

Key words: chlorophyll-a, chlorin, transformation for exocyclic ring, chlorophyllous degradation derivative, chemical reaction

Cite this article

Zhang Shanguo, Li Jiazhu, Zhang Peng, Qi Caixia, Wang Jinjun. Transformation for Exocyclic Ring of Pheophorbide and Syn-thesis of Chlorophyllous Degradation Derivatives[J]. Chin. J. Org. Chem., 2015, 35(5): 1060-1068.

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[1] (a) Pavlov, V. Y.; Ponomarev, G. V. Chem. Heterocycl. Compd. 2004, 40, 393. (b) Chen, Y. H.; Li, G. L.; Pandey, R. K. Cur. Org. Chem. 2004, 8, 1105. (c) Wang, J.-J. Chin. J. Org. Chem. 2005, 25, 1353 (in Chinese). (王进军, 有机化学, 2005, 25, 1353.) (d) Yang, Z.; Wang, Z.; Liu, Y.; Xu, X.-S.; Qi, C.-X.; Wang, J.-J. Chin. J. Org. Chem. 2013, 33, 116 (in Chinese). (杨泽, 王振, 刘洋, 徐希森, 祁彩霞, 王进军, 有机化学, 2013, 33, 116.)
[2] (a) Kozyrev, A.; Ethirajan, M,; Chen, P.; Ohkubo, K.; Robinson, GB. C.; Berkigia, K. M.; Fukuzumi, S.; Kadish, K. M.; Pandey, J. J. Org. Chem. 2012, 77, 10260. (b) Kozyrey, A. N.; Chen, Y.-H.; Goswami, L. N.; Tabaczynaki, W. A.; Pandey, R. K. J. Org. Chem. 2006, 71, 1949. (c) Liu, R.-R.; Wang, L.-M.; Yin, J.-G.; Wu, J.; Liu, C.; Zhang, P.; Wang, J.-J. Chin. J. Org. Chem. 2012, 32, 318 (in Chinese). (刘冉冉, 王鲁敏, 金英学, 武进, 刘超, 王朋, 王进军, 有机化学, 2012, 32, 318.)
[3] (a) Wang, J.-J.; Yin, Y.-F.; Yang, Z. J. Iran. Chem. Soc. 2013, 10, 583. (b) Tamiaki, H.; Monobe, R.; Koizumi, S.; Miyatake, T.; Kinoshita, Y. Tetrahedron: Asymmerty 2013, 24, 966. (c) Srivatsan, A.; Wang, Y.-F.; Joshi, P.; Sajjad, M.; Chen, Y.-H.; Liu, C.; Thankcppan, K.; Missert, J. R.; Tracy, E.; Morgan, J.; Rigual, N.; Baumann, H.; Pandey, R. K. J. Med. Chem. 2011, 54, 6859.
[4] (a) Li, J.-Z.; Liu, W.-H.; Li, F.-G.; Wang, J.-J.; Suo, Y.-R.; Liu, Y.-J. Chin. J. Org. Chem. 2007, 27, 1594 (in Chinese). (李家柱, 刘万卉, 李付国, 王进军, 索有瑞, 刘永军, 有机化学, 2007, 27, 1594.) (b) Wang, J.-J.; Li, J.-Z.; Jakus, J.; Shin, K. J. Porphyrins Phthalocyanines 2012, 16, 122.
[5] (a) Li, J.-Z.; Wang, J.-J.; Yoon, L.; Cui, B.-C.; Shim, Y.-K. Bioorg. Med. Chem. Lett. 2012, 22, 1846. (b) Wang, L.-M.; Wang, P.; Liu, C.; Jin, Y.-X.; Wang, J.-J. Chin. J. Org. Chem. 2012, 32, 1707 (in Chinese). (王鲁敏, 王朋, 刘超, 金英学, 王进军, 有机化学, 2012, 32, 1707.)
[6] Ji, J.-Y.; Wang, L. M.; Jing, J.-R.; Han, G.-F.; Wang, J.-J. Chin. J. Org. Chem. 2007, 27, 493 (in Chinese). (纪建业, 王鲁民, 荆济荣, 韩光范, 王进军, 有机化学, 2007, 27, 493.)
[7] Li, Y.-W. M.S. Thesis, Yantai University, Yantai, 2009 (in Chinese). (李韵伟, 硕士论文, 烟台大学, 烟台, 2009.)
[8] (a) Yin, J.-G.; Wang, Z.; Yang, Z.; Liu, C.; Zhao, L.-L.; Wang, J.-J. Chin. J. Org. Chem. 2012, 32, 360 (in Chinese). (殷军港, 王振, 杨泽, 刘超, 赵丽丽, 王进军, 有机化学, 2012, 32, 360.) (b) Wang, J.-J.; Zhao, Y.; Wu, X.-R.; Han, G.-F.; Shin, 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.) (c) Shin-ichi Sasaki, S.; Yoshizato, M.; Kunieda, M.; Tamiaki, H. Eur. J. Org. Chem. 2010, 5287.
[9] Wu, J. M.S. Thesis, Yantai University, Yantai, 2011 (in Chinese). (武进, 硕士论文, 烟台大学, 烟台, 2011.)
[10] Smith, K. M.; Gogg, D. A.; Simpson, D. J. J. Am. Chem. Soc. 1985, 107, 4946.

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脱镁叶绿酸的外接环转换与芳环取代叶绿素降解衍生物的合成

Transformation for Exocyclic Ring of Pheophorbide and Syn-thesis of Chlorophyllous Degradation Derivatives

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