(E)-ethyl 3-(5-chloro-1-methyl-1H-indol-3-yl)acrylate | 943825-63-6

• 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: (E)-ethyl 3-(5-chloro-1-methyl-1H-indol-3-yl)acrylate
• 英文别名: ethyl 3-(5-chloro-1-methylindol-3-yl)prop-2-enoate；ethyl (E)-3-(5-chloro-1-methylindol-3-yl)prop-2-enoate
• CAS: 943825-63-6
• 化学式: C₁₄H₁₄ClNO₂
• 分子量: 263.724
• InChiKey: MLQDTVOQRHHMCX-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 3-(5-chloro-1-methyl-1H-indol-3-yl)acrylate 在 镍 sodium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 生成 3-(5-chloro-1-methylindol-3-yl)propanoic acid
  参考文献：
  名称：

  Synthetic N-pyridinyl(methyl)-indol-3-ylpropanamides as new potential immunosuppressive agents

  摘要：

  Several N-pyridinyl(methyl)-indol-3-ylpropanamides were synthesized and pharmacological evaluations of their immumosuppressive potential were performed. Among thirteen compounds tested in vitro on murine T proliferation, three showed interesting inhibiting activity. For the most active compound (propanamide 18), immunosuppressive activity was documented both in vitro on human T lymphocytes proliferation and in vivo on mice delayed-type hypersensitivity. These experimental data demonstrated that these compounds hold potential as immunosuppressive agents. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.12.013
• 作为产物：
  描述：

  5-氯吲哚-3-甲醛 在 sodium hydride 、 caesium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.5h， 生成 (E)-ethyl 3-(5-chloro-1-methyl-1H-indol-3-yl)acrylate
  参考文献：
  名称：

  Synthetic N-pyridinyl(methyl)-indol-3-ylpropanamides as new potential immunosuppressive agents

  摘要：

  Several N-pyridinyl(methyl)-indol-3-ylpropanamides were synthesized and pharmacological evaluations of their immumosuppressive potential were performed. Among thirteen compounds tested in vitro on murine T proliferation, three showed interesting inhibiting activity. For the most active compound (propanamide 18), immunosuppressive activity was documented both in vitro on human T lymphocytes proliferation and in vivo on mice delayed-type hypersensitivity. These experimental data demonstrated that these compounds hold potential as immunosuppressive agents. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.12.013

文献信息

• Mechanochemically Activated Oxidative Coupling of Indoles with Acrylates through C–H Activation: Synthesis of 3-Vinylindoles and β,β-Diindolyl Propionates and Study of the Mechanism
  作者：Kan-Yan Jia、Jing-Bo Yu、Zhi-Jiang Jiang、Wei-Ke Su

  DOI：10.1021/acs.joc.6b01138

  日期：2016.7.15

  Construction of 3-vinylindoles (3) and β,β-diindolyl propionates (4) through solvent-free C–H functionalization has been explored under high-speed ball-milling conditions. The reaction selectivity is influenced by the catalyst dramatically: Pd(OAc)2 provides 3 in moderate to good yields, whereas PdX2 (X = Cl, I) affords 4 as the major products. The reaction mechanism has been further studied by using

  在高速球磨条件下，已经探索了通过无溶剂的C–H功能化来构建3-乙烯基吲哚（3）和β，β-二吲哚基丙酸酯（4）。反应选择性受到催化剂的极大影响：Pd（OAc）2提供3到中等至良好的收率，而PdX 2（X = Cl，I）提供4作为主要产物。通过使用电喷雾电离质谱法进一步研究了反应机理，其中以二聚钯配合物A为关键中间体解释了选择性。