3-((E)-2-Carboxy-2-fluoro-vinyl)-4,6-dichloro-1H-indole-2-carboxylic acid ethyl ester | 245510-54-7

• 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: 3-((E)-2-Carboxy-2-fluoro-vinyl)-4,6-dichloro-1H-indole-2-carboxylic acid ethyl ester
• CAS: 245510-54-7
• 化学式: C₁₄H₁₀Cl₂FNO₄
• 分子量: 346.142
• InChiKey: UIIQEAWYWYYDQV-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  79.39
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-((E)-2-Carboxy-2-fluoro-vinyl)-4,6-dichloro-1H-indole-2-carboxylic acid ethyl ester 在 lithium hydroxide 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 生成 3-[(E)-3-anilino-2-fluoro-3-oxoprop-1-enyl]-4,6-dichloro-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  Substituted Indole-2-carboxylates as Potent Antagonists of the Glycine Binding Site Associated with the NMDA Receptor

  摘要：

  A novel series of indole-2-carboxylate analogues of GV 150526 (1) in which the propenoic double bond was substituted with different "probes" or replaced by a isosteric cyclopropyl moiety were synthesized and evaluated for their affinity profile in order to obtain further information on the pharmacophoric model of the glycine binding site associated to the NMDA receptor.

  DOI：

  10.1002/(sici)1521-4184(19998)332:8<271::aid-ardp271>3.0.co;2-x
• 作为产物：
  描述：

  1-tert-butoxycarbonyl-3-formyl-4,6-dichloroindole-2-carboxylic acid ethyl ester 在 甲酸 、 potassium tert-butylate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 3-((E)-2-Carboxy-2-fluoro-vinyl)-4,6-dichloro-1H-indole-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Substituted Indole-2-carboxylates as Potent Antagonists of the Glycine Binding Site Associated with the NMDA Receptor

  摘要：

  A novel series of indole-2-carboxylate analogues of GV 150526 (1) in which the propenoic double bond was substituted with different "probes" or replaced by a isosteric cyclopropyl moiety were synthesized and evaluated for their affinity profile in order to obtain further information on the pharmacophoric model of the glycine binding site associated to the NMDA receptor.

  DOI：

  10.1002/(sici)1521-4184(19998)332:8<271::aid-ardp271>3.0.co;2-x