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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (10): 1548-1554. 上一篇    下一篇

研究简报

脯氨酸催化新型3-α,β-不饱和酮取代-4-羟基喹啉-2-酮简便合成及其荧光性质研究

叶家海*,1，吴俊2，黄年峰1，张文超1，余述燕2，秦志春1，王智勇1，商永嘉*,2   

  1. (1南京理工大学化工学院 南京 210094)
    (2安徽师范大学化学与材料科学学院 安徽省分子固体重点实验室 芜湖 241000)
  • 收稿日期:2010-01-15 修回日期:2010-03-29 发布日期:2010-05-14
  • 通讯作者: 叶家海 E-mail:yjhnjunjust@sina.com
  • 基金资助:

    基于烯酮亚胺的多组分反应合成一些环状化合物的方法学研究

Study on Proline-Catalyzed Facile Synthesis of Novel 3-(α,β- Unsaturated carbonyl)-4-hydroxy-quinolin-2(1H)-ones and Their Fluorescent Properties

Ye Jiahai*,1 Wu Jun2 Huang Nianfeng1 Zhang Wenchao1 Yu Shuyan2 Qin Zhichun1 Wang Zhiyong1 Shang Yongjia*,2   

  1. (1 School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094)
    (2 Anhui Key Laboratory of Functional Molecular Solids, College of Chemistry and Material Science, Anhui Normal University, Wuhu 241000)
  • Received:2010-01-15 Revised:2010-03-29 Published:2010-05-14

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3-乙酰-4-羟基喹啉-2-酮和芳香醛在L-脯氨酸有效催化下发生Aldol反应, 生成一系列缩合产物3-α,β-不饱和酮取代-4-羟基喹啉-2-酮. 该反应在甲醇溶液中进行, 并且产物作为沉淀直接从溶液中析出, 简单洗涤可得纯产物. 研究表明芳香醛上的取代基性质对产物的产率有显著影响, 其结果证实了该缩合反应经历了一个脱水中间体的反应历程. 此外, 对产物的荧光性质研究表明该类化合物可作为潜在应用价值的有机光学材料.

关键词: 脯氨酸, Aldol反应, 4-羟基喹啉-2-酮, 荧光

The aldol reaction of 3-acetyl-4-hydroxy-2(1H)-ones with aromatic aldehydes catalyzed by L-proline was carried out to give novel 3-(α,β-unsaturated car-bonyl)-4-hydroxy-2(1H)-ones which were separated from the solvent as pure compounds efficiently. The yields of products were affected by the properties of substitutes in aromatic aldehydes. This result con-firmed a new reaction mechanism. The study on the fluorescent properties of some products revealed that this class of compounds is potential fluorescent probes.

Key words: proline, aldol reaction, 4-hydroxy-quinolin-2-one, fluorescence