Ethyl 2-(2-phenylindol-1-yl)cyclopentene-1-carboxylate | 1103523-11-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: Ethyl 2-(2-phenylindol-1-yl)cyclopentene-1-carboxylate
• CAS: 1103523-11-0
• 化学式: C₂₂H₂₁NO₂
• 分子量: 331.414
• InChiKey: BYGYBWSRKBDGTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-苯基乙炔基胺 、 2-氧代环戊羧酸乙酯 在 indium(III) bromide 作用下， 以 甲苯 为溶剂， 以94%的产率得到Ethyl 2-(2-phenylindol-1-yl)cyclopentene-1-carboxylate
  参考文献：
  名称：

  Tandem β-Enamino Ester Formation and Cyclization with o-Alkynyl Anilines Catalyzed by InBr₃: Efficient Synthesis of β-(N-Indolyl)-α,β-unsaturated Esters

  摘要：

  A tandem reaction providing beta-(N-indolyl)-alpha,beta-unsaturated esters from beta-keto esters and o-alkynyl anilines was developed. Z-Alkenes were selectively formed due to the stability of the beta-enamino ester as an intermediate of the reaction. This reaction includes the intermolecular beta-enamino ester formation and intramolecular cyclization catalyzed by InBr3.

  DOI：

  10.1021/jo802435b

文献信息

• Tandem β-Enamino Ester Formation and Cyclization with <i>o</i>-Alkynyl Anilines Catalyzed by InBr₃: Efficient Synthesis of β-(<i>N</i>-Indolyl)-α,β-unsaturated Esters
  作者：Kenichi Murai、Shoko Hayashi、Nobuhiro Takaichi、Yasuyuki Kita、Hiromichi Fujioka

  DOI：10.1021/jo802435b

  日期：2009.2.6

  A tandem reaction providing beta-(N-indolyl)-alpha,beta-unsaturated esters from beta-keto esters and o-alkynyl anilines was developed. Z-Alkenes were selectively formed due to the stability of the beta-enamino ester as an intermediate of the reaction. This reaction includes the intermolecular beta-enamino ester formation and intramolecular cyclization catalyzed by InBr3.