ethyl 3,3-bis(2-methyl-1H-indol-3-yl)propanoate | 29278-65-7

• 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 3,3-bis(2-methyl-1H-indol-3-yl)propanoate
• 英文别名: 3,3-bis-(2-methyl-indol-3-yl)-propionic acid ethyl ester
• CAS: 29278-65-7
• 化学式: C₂₃H₂₄N₂O₂
• 分子量: 360.456
• InChiKey: KKDCBVITSLSSFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  57.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-甲基吲哚 、 丙炔酸乙酯 在 iron(III) chloride 、 silver trifluoromethanesulfonate 、 溶剂黄146 作用下， 反应 96.0h， 以70%的产率得到ethyl 3,3-bis(2-methyl-1H-indol-3-yl)propanoate
  参考文献：
  名称：

  Regioselective synthesis of 3,3-bis(indolyl)propanoic acid derivatives by iron(III)-catalyzed hydroarylation of propynoic acid derivatives with indoles

  摘要：

  Intermolecular hydroarylation of propynoic acid and its esters with indoles proceeded efficiently in acetic acid under a catalytic system of FeCl3/3AgOTf and afforded the corresponding 3,3-bis(indol-3yl) propanoic acids and their esters in high yields. In the case of 2-methylindole, 3-indolylacrylic acid and its ethyl ester were obtained in high yields. This iron-catalyzed hydroarylation showed a high regioselectivity at the 3-position of indoles and a high utility for the synthesis of bis(indol-3-yl) compounds, which are important for biological and pharmaceutical fields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.051

文献信息

• Ga(DS)3-catalysed double hydroarylation of acetylenic esters with indoles for the synthesis of bisindolyl propanoates
  作者：Li-Tao An、Jing-Jing Cai、Xiang-Qiang Pan、Tang-Ming Chen、Jian-Ping Zou、Wei Zhang

  DOI：10.1016/j.tetlet.2015.05.024

  日期：2015.6

  An efficient synthetic method for bisindolyl propanoates has been developed. Ga(DS)(3)-catalysed double hydroarylation of acetylenic esters with indoles in water afforded regioselective products with up to 99% yield. (C) 2015 Published by Elsevier Ltd.
• Regioselective synthesis of 3,3-bis(indolyl)propanoic acid derivatives by iron(III)-catalyzed hydroarylation of propynoic acid derivatives with indoles
  作者：Md. Shahajahan Kutubi、Tsugio Kitamura

  DOI：10.1016/j.tet.2011.08.051

  日期：2011.10

  Intermolecular hydroarylation of propynoic acid and its esters with indoles proceeded efficiently in acetic acid under a catalytic system of FeCl3/3AgOTf and afforded the corresponding 3,3-bis(indol-3yl) propanoic acids and their esters in high yields. In the case of 2-methylindole, 3-indolylacrylic acid and its ethyl ester were obtained in high yields. This iron-catalyzed hydroarylation showed a high regioselectivity at the 3-position of indoles and a high utility for the synthesis of bis(indol-3-yl) compounds, which are important for biological and pharmaceutical fields. (C) 2011 Elsevier Ltd. All rights reserved.