4,6-dichloro-3-formyl-1-(2-trimethylsilanylethoxymethyl)-indole-2-carboxylic acid ethyl ester | 153435-97-3

• 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-formyl-1-(2-trimethylsilanylethoxymethyl)-indole-2-carboxylic acid ethyl ester
• 英文别名: 1-(2-(trimethylsilyl)ethoxymethyl)-3-formyl-4,6-dichloroindole-2-carboxylic acid ethyl ester；Ethyl 4,6-dichloro-3-formyl-1-(2-trimethylsilylethoxymethyl)indole-2-carboxylate
• CAS: 153435-97-3
• 化学式: C₁₈H₂₃Cl₂NO₄Si
• 分子量: 416.376
• InChiKey: JPPVWMBBLRVYDE-UHFFFAOYSA-N

物化性质

• 沸点：
  517.1±50.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.25
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,6-dichloro-3-formyl-1-(2-trimethylsilanylethoxymethyl)-indole-2-carboxylic acid ethyl ester 在 盐酸 、 lithium hydroxide 、 叔丁基锂 、 三甲基硅烷化重氮甲烷 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 15.17h， 生成 4,6-二氯-3-[(E)-(2-氧代-1-苯基-3-吡咯烷基亚基)甲基]-1H-吲哚-2-羧酸
  参考文献：
  名称：

  Unusual synthesis of new glycine antagonists via sequential aldol condensation-lactonization-elimination reaction

  摘要：

  Compounds 2 and 3 were designed in older to probe the North-East region of the strichnine-insensitive glycine binding site of the NMDA receptor. The two products were obtained readily by a tandem aldol condensation-lactonization-elimination step which affords the desired E isomer with complete regioselection. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00284-4
• 作为产物：
  描述：

  2-(三甲基硅烷基)乙氧甲基氯 、 4,6-二氯-3-甲酰基-1H-吲哚-2-甲酸乙酯 在 lithium hexamethyldisilazane 作用下， 以 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以93%的产率得到4,6-dichloro-3-formyl-1-(2-trimethylsilanylethoxymethyl)-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

文献信息

• Synthesis of Substituted Indole-2-carboxylates: Versatile Introduction of a Carbamoyl Moiety at the C-3 Position
  作者：Simone A. Giacobbe、Romano Di Fabio、Davide Baraldi、Alfredo Cugola、Daniele Donati

  DOI：10.1080/00397919908085936

  日期：1999.9

  This paper deals with a novel and versatile synthetic approach for the introduction of a functionalized ethynyl side chain at the C-3 position of the 2-carboxyindole nucleus. The key step of this process is represented by the coupling reaction between the dianion deriving from the 2-carboxylate-3-acetylide with different isocyanates.
• Unusual synthesis of new glycine antagonists via sequential aldol condensation-lactonization-elimination reaction
  作者：Simone A. Giacobbe、Davide Baraldi、Romano Di Fabio

  DOI：10.1016/s0960-894x(98)00284-4

  日期：1998.7

  Compounds 2 and 3 were designed in older to probe the North-East region of the strichnine-insensitive glycine binding site of the NMDA receptor. The two products were obtained readily by a tandem aldol condensation-lactonization-elimination step which affords the desired E isomer with complete regioselection. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Substituted Indole-2-carboxylates as Potent Antagonists of the Glycine Binding Site Associated with the NMDA Receptor
  作者：Fabrizio Micheli、Romano Di Fabio、Davide Baraldi、Nadia Conti、Alfredo Cugola、Paola Gastaldi、Simone Giacobbe、Carla Marchioro、Manolo Mugnaini、Luciana Rossi、Angelo Pecunioso、Giorgio Pentassuglia

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

  日期：1999.8

  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.