5-Methyl-2-(dimethylsilyl)-1H-indole-1-carboxylic acid tert-butyl ester | 475102-17-1

• 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: 5-Methyl-2-(dimethylsilyl)-1H-indole-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 2-dimethylsilyl-5-methylindole-1-carboxylate
• CAS: 475102-17-1
• 化学式: C₁₆H₂₃NO₂Si
• 分子量: 289.45
• InChiKey: RIECPYZYOLVSJK-UHFFFAOYSA-N

物化性质

• 沸点：
  383.2±34.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为产物：
  描述：

  5-甲基吲哚 在 4-二甲氨基吡啶 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.25h， 生成 5-Methyl-2-(dimethylsilyl)-1H-indole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  A Non-cryogenic Method for the Preparation of 2-(Indolyl) Borates, Silanes, and Silanols

  摘要：

  2-Indolyl borates are prepared via addition of LDA to a mixture of N-Boc-indole and triisopropyl borate at 0-5 degreesC. Following acidic hydrolysis, the boronic acids are isolated by crystallization in good to excellent yield (73-99%). The method is quite general, tolerating a wide range of functional groups, and also provides access to 2-silyl derivatives (80-91%).

  DOI：

  10.1021/jo026087j

文献信息

• A Non-cryogenic Method for the Preparation of 2-(Indolyl) Borates, Silanes, and Silanols
  作者：Enrique Vazquez、Ian W. Davies、Joseph F. Payack

  DOI：10.1021/jo026087j

  日期：2002.10.1

  2-Indolyl borates are prepared via addition of LDA to a mixture of N-Boc-indole and triisopropyl borate at 0-5 degreesC. Following acidic hydrolysis, the boronic acids are isolated by crystallization in good to excellent yield (73-99%). The method is quite general, tolerating a wide range of functional groups, and also provides access to 2-silyl derivatives (80-91%).