4,6-Dichloro-3-((Z)-2-fluoro-2-phenylcarbamoyl-vinyl)-1H-indole-2-carboxylic acid ethyl ester | 245510-52-5

• 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: 4,6-Dichloro-3-((Z)-2-fluoro-2-phenylcarbamoyl-vinyl)-1H-indole-2-carboxylic acid ethyl ester
• CAS: 245510-52-5
• 化学式: C₂₀H₁₅Cl₂FN₂O₃
• 分子量: 421.255
• InChiKey: YTYVXQCXUQKNCG-GDNBJRDFSA-N

物化性质

• 沸点：
  659.9±55.0 °C(predicted)
• 密度：
  1.465±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  71.19
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4,6-Dichloro-3-((Z)-2-fluoro-2-phenylcarbamoyl-vinyl)-1H-indole-2-carboxylic acid ethyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 22.0h， 以60%的产率得到3-[(Z)-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 、 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 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 5.0h， 生成 4,6-Dichloro-3-((Z)-2-fluoro-2-phenylcarbamoyl-vinyl)-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