1-Tri(propan-2-yl)silylindole-5-carboxylic acid | 540776-64-5

• 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: 1-Tri(propan-2-yl)silylindole-5-carboxylic acid
• CAS: 540776-64-5
• 化学式: C₁₈H₂₇NO₂Si
• 分子量: 317.503
• InChiKey: DWPUQTVYISXLPG-UHFFFAOYSA-N

物化性质

• 沸点：
  383.5±24.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.36
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-苄氧基苯甲醛 、 1-Tri(propan-2-yl)silylindole-5-carboxylic acid 以36%的产率得到1-(3-phenylmethoxyphenyl)-6-tri(propan-2-yl)silyl-1H-furo[3,4-e]indol-3-one
  参考文献：
  名称：

  Solid-phase lithiation of 5-carboxyindoles

  摘要：

  Direct functionalization of protected 5-carboxyindole by metalation has been performed for the first time on solid-phase. The indole moiety has been tethered to aminomethylated polytetrahydrofuran cross-linked polystyrene, forming a secondary amide, which functions as a directing metalation group. The ortho-lithiated species have been quenched with substituted benzaldehydes affording resin bound alcohols. After cyclative cleavage regioisomeric mixtures of phthalides were obtained in the ratio 80:20. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00175-8
• 作为产物：
  描述：

  5-溴吲哚 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-Tri(propan-2-yl)silylindole-5-carboxylic acid
  参考文献：
  名称：

  Solid-phase lithiation of 5-carboxyindoles

  摘要：

  Direct functionalization of protected 5-carboxyindole by metalation has been performed for the first time on solid-phase. The indole moiety has been tethered to aminomethylated polytetrahydrofuran cross-linked polystyrene, forming a secondary amide, which functions as a directing metalation group. The ortho-lithiated species have been quenched with substituted benzaldehydes affording resin bound alcohols. After cyclative cleavage regioisomeric mixtures of phthalides were obtained in the ratio 80:20. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00175-8

文献信息

• Solid-phase lithiation of 5-carboxyindoles
  作者：Jan Tois、Ari Koskinen

  DOI：10.1016/s0040-4039(03)00175-8

  日期：2003.3

  Direct functionalization of protected 5-carboxyindole by metalation has been performed for the first time on solid-phase. The indole moiety has been tethered to aminomethylated polytetrahydrofuran cross-linked polystyrene, forming a secondary amide, which functions as a directing metalation group. The ortho-lithiated species have been quenched with substituted benzaldehydes affording resin bound alcohols. After cyclative cleavage regioisomeric mixtures of phthalides were obtained in the ratio 80:20. (C) 2003 Elsevier Science Ltd. All rights reserved.