研究论文

涉及碳-碳键断裂的克莱森-施密特缩合反应

  • 杨永青 ,
  • 朱孟楠 ,
  • 陆征 ,
  • 陈立婷 ,
  • 苏静
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  • 江苏大学药学院 镇江 212013

收稿日期: 2015-09-29

  修回日期: 2015-11-09

  网络出版日期: 2016-01-04

基金资助

国家自然科学基金(No.21572118)、江苏高校优势学科建设工程(PAPD)和江苏大学高级人才启动基金(Nos.10JDG042,14JDG018)资助项目.

Claisen-Schmidt Condensation Involved with C—C Bond Cleavage

  • Yang Yong-Qing ,
  • Zhu Meng-Nan ,
  • Lu Zheng ,
  • Chen Li-Ting ,
  • Su Jing
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  • School of Pharmacy, Jiangsu University, Zhenjiang 212013

Received date: 2015-09-29

  Revised date: 2015-11-09

  Online published: 2016-01-04

Supported by

Project supported by the National Natural Science Foundation of China (No. 21572118), the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD) and the Jiangsu University Startup Funding for Talented Researcher (Nos. 10JDG042, 14JDG018).

摘要

研究了BaOH2促进的β-二酮与芳香醛的克莱森-施密特反应,反应产物可能为单烯烃或双烯烃化合物.单烯烃的生成涉及碳-碳键的断裂,双烯烃产物是姜黄素的三元环类似物.

本文引用格式

杨永青 , 朱孟楠 , 陆征 , 陈立婷 , 苏静 . 涉及碳-碳键断裂的克莱森-施密特缩合反应[J]. 有机化学, 2016 , 36(5) : 1073 -1079 . DOI: 10.6023/cjoc201509040

Abstract

Claisen-Schmidt condensation of β-diketone and aryl aldehyde is studied. The reaction product could be mono-or di-alkene. C—C bond cleavage is involved in the production of monoalkene. While the dialkene products are three-membered ring analogues of curcumin.

参考文献

[1] (a) Vollhardt, P.; Schore, N. Organic Chemistry-Structure and Function, W. H. Freeman and Company, New York, 2009, p. 856.
(b) Albuquerque, H. M. T.; Santos, C. M. M.; Cavaleiro, J. A. S.; Silva, A. M. S. Curr. Org. Chem. 2010, 18, 2750.
[2] (a) Mahapatra, D. K.; Asati, V.; Bharti, S. Eur. J. Med. Chem. 2015, 92, 839.
(b) Avupati, V. R.; Yejella, R. P. J. Pharm. Pharm. Sci. 2014, 3, 1713.
[3] (a) Umezawa, T.; Seino, T.; Matsuda, F. Org. Lett. 2012, 14, 4206.
(b) El-Batta, A.; Jiang, C.; Zhao, W.; Anness, R.; Cooksy, A. L.; Bergdahl, M. J. Org. Chem., 2007, 72, 5244.
[4] Ma, X.-T.; Wang, Y.; Dai, R.-H.; Liu, C.-R.; Tian, S.-K. J. Org. Chem. 2013, 78, 11071.
(b) Kwon, M. S.; Kim, N.; Seo, S. H.; Park, I. S.; Cheedrala, R. K.; Park, J. Angew. Chem., Int. Ed. 2005, 42, 6913.
(c) Rhee, J. U.; Krishe, M. J. Org. Lett. 2005, 7, 2493.
[5] (a) Wang, Z.; Yin, G.; Qin, J.; Gao, M.; Cao, L.; Wu, A. Synthesis 2008, 3565.
(b) Qiu, R.; Qiu, Y.; Meng, Z.; Song, X.; Jia, Z.; Yu, K.; Yin, S. Adv. Mater. Phys. Chem. 2012, 2, 142.
(c) Erkkilä, A.; Pinko, P. M. J. Org. Chem. 2006, 71, 2538.
(d) Rueping, M.; Bootwicha, T.; Baars, H.; Sugiono, E. Beilstein J. Org. Chem. 2011, 7, 1680.
(e) Li, Y.; Chen, D. Chin. J. Chem. 2011, 29, 2086.
(f) Yanagisawa, A.; Goudu, R.; Arai, T. Org. Lett. 2004, 6, 4281.
(g) Zhang, X.; Feng, X.; Liu, H.; Qin, Y.; Dai, Y. Chin. J. Catal. 2012, 33, 523.
[6] (a) Claisen, L.; Claparède, A. Ber. Dtsch. Chem. Ges. 1881, 14, 2460.
(b) Schmidt, J. G. Ber. Dtsch. Chem. Ges. 1881, 14, 1459.
[7] (a) Manojveer, S.; Balamurugan, R. Org. Lett. 2015, 17, 3600.
(b) Passalacqua, T. G.; Dutra, L. A.; de Almeida, L.; Velasquez. A. M. A.; Torres, F. A. E.; Yamasaki, P. R.; dos Santos, M. B.; Regasini, L. O.; Michels, P. A. M.; Bolzani, V. D. Bioorg. Med. Chem. Lett. 2015, 25, 3342.
(c) Rayar, A.; Veitía, M. S.-I.; Ferroud, C. SpringerPlus 2015, 4, 221.
(d) Amin, K. M.; Abou-Seri, S. M.; Awadallah, F. M.; Eissa, A. A. M.; Hassan, G. S.; Abdulla, M. M.; Eur. J. Med. Chem. 2015, 90, 221.
[8] Shoji, M.; Nakagawa, K.; Watanabe, A.; Tsuduki, T.; Yamada, T.; Kuwahara, S.; Kimura, F.; Myyazawa, T. Food Chem. 2014, 151, 126.
(b) Vnallinou, N. G.; Evagelopoulos, A.; Schizas, N.; Kazazis, C. Anticancer Res. 2015, 35, 645.
(c) Hasima, N.; Aggarwal, B. B. Curr. Med. Chem. 2014, 21, 1583.
[9] (a) Lin, L.; Hutzen, B.; Zuo, M.; Ball, S.; Deangelis, S.; Foust, E.; Pandit, B.; Ihnat, M. A.; Shenoy, S. S.; Kulp, S.; Li, P.-K.; Li, C.; Fuchs, J.; Lin, J. Cancer Res. 2010, 70, 2445.
(b) Li, P.-K.; Li, C.; Lin, J.; Fuchs, J. R. WO 2010/121007, 2010[Chem. Abstr. 2010, 153, 546757].
(c) Bill, M. A.; Nicholas, C.; Mace, T. A.; Etter, J. P.; Li, C; Schwartz, E. B.; Fuchs, J. R.; Young, G. S.; Lin, L.; Lin, J.; He, L.; Phelps, M.; Li, P.-K.; Lesinski, G. B. PloS One 2012, 7, e40724.
[10] Mai, A.; Cheng, D.; Bedford, M. T.; Vlaente, S.; Nebbioso, A.; Perrone, A.; Brosch, G.; Sbardella, G.; De Bellis, F.; Miceli, M.; Altucci, L. J. Med. Chem. 2008, 51, 2279.
[11] Leow, P.-C.; Bahety, P.; Boon. C. P.; Lee, C. Y.; Tan, K. L.; Yang, T.; Ee, P.-L. R. Eur. J. Med. Chem. 2014, 71, 67.
[12] The general work up procedure is: Ethyl acetate extract after acidification with dilute hydrochloride followed with water, sodium bicarbonate, and brine wash. The combined organic phase was dried and then concentrated to afford a residue for flash chromatography. In this procedure, acidic material would be removed by sodium bicarbonate wash. In these entries, the sodium bicarbonate wash step was skipped. The residue was dissolved in dichloromethane (2 mL), and then solid insoluble was washed with dichloromethane (0.5 mL×2). The solid was characterized as cinnamic acids 10a, 10c and 10d.
[13] (a) Ameen, D.; Snape, T. J. Tetrahedron Lett. 2015, 56, 1816.
(b) Zheng, W.; Wang, Y.; Bai, C.; Wen, J.; Wang, N. Chin. J. Chem. 2015, 33, 401.
(c) Peshkov, A. A.; Peshkov, V. A.; Li, Z.; Pereshivko, O. P.; Van der Eycken, E. V. Eur. J. Org. Chem. 2014, 6390.
(d) Xie, F.; Yan, F.; Chen, M.; Zheng, M. RSC Adv. 2014, 4, 29502.
(e) Maji, T.; Tunge, J. A. Org. Lett. 2014, 16, 5072.
(f) Roudier, M.; Constantieux, T.; Quintard, A.; Rodriguez, J. Org. Lett. 2014, 16, 2802.
(g) Maji, T.; Ramakumar, K. Tunge, J. A. Chem. Commun. 2014, 50, 14045.
(h) Zhou, Y.; Yang, D.; Luo, G.; Luo, Y.; Xue, N.; Qu, J. Tetrahedron 2014, 70, 4668.
(i) Yang, D.; Zhou, Y.; Xue, N.; Qau, J. J. Org. Chem. 2013, 78, 4171.
[14] Ojima, F.; Osa, T. Bull. Chem. Soc. Jpn. 1989, 62, 3187.
[15] (a) Muthusamy, S.; Gnanaprakasam, B. Tetrahedron Lett. 2005, 46, 635.
(b) Gerken, J. B.; Wang, S. C.; Preciado, A. B.; Park, Y. S.; Nishiguchi, G.; Tantillo, D. J.; Little, R. D. J. Org. Chem. 2005, 70, 4598.
[16] Inaba, S.-I.; Rieke, R. D. J. Org. Chem. 1985, 50, 1373.
[17] Coveney, D. J.; Patel, V. F.; Pattenden, G.; Thompson, D. M. J. Chem. Soc., Perkin Trans. 1 1990, 2721.
[18] Brittelli, D. R. J. Org. Chem. 1981, 46, 2514.
[19] Wang, D.; Zhang, Y.; Harris, A.; Gautam, L. N. S.; Chen, Y.; Shi, X. Adv. Synth. Catal. 2011, 353, 2584.
[20] Basaif, S. A.; Sobahi, T. R. J. King Abdulaziz Univ.: Sci. 2005, 17, 107.
[21] Suresh; Kumar, D.; Sandhu, J. S. Synth. Commun. 2010, 40, 1915.
[22] Ghorai, P.; Kraus, A.; Keller, M.; Götte, C.; Igel, P.; Schneider, E.; Schnell, D.; Bernhardt, G.; Dove, S.; Zabel, M.; Elz, S.; Seifert, R.; Bushauer, A. J. Med. Chem. 2008, 51, 7193.

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