ethyl 1-benzyl-2-phenyl-1H-indole-3-carboxylate | 77435-12-2

• 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-benzyl-2-phenyl-1H-indole-3-carboxylate
• 英文别名: ethyl 1-benzyl-2-phenylindole-3-carboxylate
• CAS: 77435-12-2
• 化学式: C₂₄H₂₁NO₂
• 分子量: 355.436
• InChiKey: IHSOJQFAWGULKJ-UHFFFAOYSA-N

物化性质

• 熔点：
  108-113 °C(Solv: ethanol (64-17-5))
• 沸点：
  564.4±45.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  (E)-3-(N'-Benzyl-N'-phenyl-hydrazino)-3-phenyl-acrylic acid ethyl ester 以 乙二醇 为溶剂， 反应 2.5h， 以2.1 g的产率得到ethyl 1-benzyl-2-phenyl-1H-indole-3-carboxylate
  参考文献：
  名称：

  Mills, Keith; Khawaja, Ibtisam K. Al; Al-Saleh, Fowzia, Journal of the Chemical Society. Perkin transactions I, 1981, p. 636 - 641

  摘要：

  DOI：

文献信息

• A Convenient and General Method for the Synthesis of Indole-2,3-dicarboxylates and 2-Arylindole-3-carboxylates
  作者：Iliyas Ali Sayyed、Karolin Alex、Annegret Tillack、Nicolle Schwarz、Dirk Michalik、Matthias Beller

  DOI：10.1002/ejoc.200700310

  日期：2007.9

  A transition-metal-free, simple and efficient one-pot method for the synthesis of indole-2,3-dicarboxylates and 2-arylindole-3-carboxylates is described. The corresponding products are obtained by a domino hydroamination/Fischerindole cyclization in good-to-excellent yields from easily available 1-alkyl-1-phenylhydrazines and acetylene carboxylates.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim

  描述了一种无过渡金属、简单有效的单锅法合成 indole-2,3-dicarboxylates 和 2-arylindole-3-carboxylates。相应的产物是通过多米诺加氢胺化/费歇吲哚环化以从容易获得的 1-烷基-1-苯肼和乙炔羧酸盐的良好收率获得的。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• 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.
• MILLS K.; AL KHAWAJA I. K.; AL-SALEH F. S.; JOULE J. A., J. CHEM. SOC. PERKIN TRANS., PART 1, 1981, NO 2, 636-641
  作者：MILLS K.、 AL KHAWAJA I. K.、 AL-SALEH F. S.、 JOULE J. A.

  DOI：——

  日期：——