(5S)-diethyl 4-acetyl-5-(naphthalen-2-yl)-1H-pyrrole-2,2(5H)-dicarboxylate | 1357874-15-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (5S)-diethyl 4-acetyl-5-(naphthalen-2-yl)-1H-pyrrole-2,2(5H)-dicarboxylate
• 英文别名: diethyl (2S)-3-acetyl-2-naphthalen-2-yl-1,2-dihydropyrrole-5,5-dicarboxylate
• CAS: 1357874-15-7
• 化学式: C₂₂H₂₃NO₅
• 分子量: 381.428
• InChiKey: SRRAEYPSBGYXHS-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  氨基丙二酸二乙酯 、 2-萘甲醛 、 3-丁炔-2-酮 在 (S)-3,3'-双(9-蒽基)-1,1'-联萘-2,2'-二基磷酸氢酯 作用下， 以 甲苯 为溶剂， 反应 30.0h， 生成 (5R)-diethyl 4-acetyl-5-(naphthalen-2-yl)-1H-pyrrole-2,2(5H)-dicarboxylate 、 (5S)-diethyl 4-acetyl-5-(naphthalen-2-yl)-1H-pyrrole-2,2(5H)-dicarboxylate
  参考文献：
  名称：

  Highly enantioselective synthesis of biologically important 2,5-dihydropyrroles via phosphoric acid-catalyzed three-component reactions and evaluation of their cytotoxicity

  摘要：

  A series of new chiral 2,5-dihydropyrrole derivatives were synthesized with high enantioselectivity via phosphoric acid-catalyzed three-component reactions of aldehydes, amino-esters, and alkyl ynones. This approach has the prominent features of high enantioselectivity (up to 98% ee), atom economy, a broad scope of substrate tolerance as well as operational simplicity, leading to a facile and straightforward access to biologically important chiral 2,5-dihydropyrroles. Moreover, the preliminary evaluation on the cytotoxic activity of this type of chiral 2,5-dihydropyrrole derivatives has resulted in the finding of several compounds with effective cytotoxicity to the carcinoma cell line MCF7. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.11.020

文献信息

• Highly enantioselective synthesis of biologically important 2,5-dihydropyrroles via phosphoric acid-catalyzed three-component reactions and evaluation of their cytotoxicity
  作者：Feng Shi、Zhong-Lin Tao、Jie Yu、Shu-Jiang Tu

  DOI：10.1016/j.tetasy.2011.11.020

  日期：2011.12

  A series of new chiral 2,5-dihydropyrrole derivatives were synthesized with high enantioselectivity via phosphoric acid-catalyzed three-component reactions of aldehydes, amino-esters, and alkyl ynones. This approach has the prominent features of high enantioselectivity (up to 98% ee), atom economy, a broad scope of substrate tolerance as well as operational simplicity, leading to a facile and straightforward access to biologically important chiral 2,5-dihydropyrroles. Moreover, the preliminary evaluation on the cytotoxic activity of this type of chiral 2,5-dihydropyrrole derivatives has resulted in the finding of several compounds with effective cytotoxicity to the carcinoma cell line MCF7. (C) 2011 Elsevier Ltd. All rights reserved.