ethyl 1-methyl-5-phenyl-1H-indole-3-carboxylate

• 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 1-methyl-5-phenyl-1H-indole-3-carboxylate
• 英文别名: Ethyl 1-methyl-5-phenylindole-3-carboxylate；ethyl 1-methyl-5-phenylindole-3-carboxylate
• 化学式: C₁₈H₁₇NO₂
• 分子量: 279.338
• InChiKey: HDJIMZQTLCFVJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  5-苯基-1H-吲哚 在 二甲基氯化铝 、 sodium hydride 作用下， 以 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 3.5h， 生成 ethyl 1-methyl-5-phenyl-1H-indole-3-carboxylate
  参考文献：
  名称：

  Me2AlCl-mediated carboxylation, ethoxycarbonylation, and carbamoylation of indoles

  摘要：

  Various 1-methyl-, 1-triisopropylsilyl-, and 1-benzylindoles are carboxylated under CO2 pressure (3.0 MPa) with the aid of 1.0 molar equiv of Me2AlCl to give 1-substituted indole-3-carboxylic acids in good to excellent yields. Mechanistic studies suggest that the intermediate, an indol-3-ylaluminum ate complex, was reversibly formed by electrophilic addition of Me2AlCl to the substrate followed by de-protonation of the resulting adduct. This method is successfully extended to alkoxycarbonylation with ethyl chloroformate and carbamoylation with naphthalen-1-yl isocyanate, which afford ethyl indole-3-carboxylates and N-naphthalen-1-ylindole-3-carboxamides, respectively. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.12.028

文献信息

• Me2AlCl-mediated carboxylation, ethoxycarbonylation, and carbamoylation of indoles
  作者：Koji Nemoto、Shinya Tanaka、Megumi Konno、Satoru Onozawa、Masafumi Chiba、Yuuki Tanaka、Yosuke Sasaki、Ryo Okubo、Tetsutaro Hattori

  DOI：10.1016/j.tet.2015.12.028

  日期：2016.2

  Various 1-methyl-, 1-triisopropylsilyl-, and 1-benzylindoles are carboxylated under CO2 pressure (3.0 MPa) with the aid of 1.0 molar equiv of Me2AlCl to give 1-substituted indole-3-carboxylic acids in good to excellent yields. Mechanistic studies suggest that the intermediate, an indol-3-ylaluminum ate complex, was reversibly formed by electrophilic addition of Me2AlCl to the substrate followed by de-protonation of the resulting adduct. This method is successfully extended to alkoxycarbonylation with ethyl chloroformate and carbamoylation with naphthalen-1-yl isocyanate, which afford ethyl indole-3-carboxylates and N-naphthalen-1-ylindole-3-carboxamides, respectively. (C) 2015 Elsevier Ltd. All rights reserved.