3-bromoethynyl-4,6-dichloro-1-(2-trimethylsilanylethoxymethyl)-indole-2-carboxylic acid ethyl ester | 153435-99-5

• 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: 3-bromoethynyl-4,6-dichloro-1-(2-trimethylsilanylethoxymethyl)-indole-2-carboxylic acid ethyl ester
• 英文别名: Ethyl 3-(2-bromoethynyl)-4,6-dichloro-1-(2-trimethylsilylethoxymethyl)indole-2-carboxylate
• CAS: 153435-99-5
• 化学式: C₁₉H₂₂BrCl₂NO₃Si
• 分子量: 491.284
• InChiKey: NDSGXWATSIEHQC-UHFFFAOYSA-N

物化性质

• 沸点：
  541.5±60.0 °C(predicted)
• 密度：
  1.33±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.14
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-bromoethynyl-4,6-dichloro-1-(2-trimethylsilanylethoxymethyl)-indole-2-carboxylic acid ethyl ester 在 lithium hydroxide 作用下， 以 乙醇 为溶剂， 以80%的产率得到3-bromoethynyl-4,6-dichloro-1-(2-trimethylsilanylethoxymethyl)-indole-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of Substituted Indole-2-carboxylates: Versatile Introduction of a Carbamoyl Moiety at the C-3 Position

  摘要：

  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.

  DOI：

  10.1080/00397919908085936
• 作为产物：
  描述：

  4,6-二氯-3-甲酰基-1H-吲哚-2-甲酸乙酯 在 sodium hydride 、 三苯基膦 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 3-bromoethynyl-4,6-dichloro-1-(2-trimethylsilanylethoxymethyl)-indole-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of Substituted Indole-2-carboxylates: Versatile Introduction of a Carbamoyl Moiety at the C-3 Position

  摘要：

  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.

  DOI：

  10.1080/00397919908085936

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.