(5-Triisopropylsilanyloxy-2-trimethylsilanylethynyl-phenyl)-carbamic acid tert-butyl ester | 194869-22-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (5-Triisopropylsilanyloxy-2-trimethylsilanylethynyl-phenyl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[2-(2-trimethylsilylethynyl)-5-tri(propan-2-yl)silyloxyphenyl]carbamate
• CAS: 194869-22-2
• 化学式: C₂₅H₄₃NO₃Si₂
• 分子量: 461.792
• InChiKey: SAZSNVFOYOAPJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.82
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5-Triisopropylsilanyloxy-2-trimethylsilanylethynyl-phenyl)-carbamic acid tert-butyl ester 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 17.0h， 以67%的产率得到6-[(triisopropylsilyl)oxy]indole
  参考文献：
  名称：

  General and Facile Synthesis of Indoles with Oxygen-Bearing Substituents at the Benzene Moiety

  摘要：

  Indoles with oxygen-bearing substituents such as a methoxy or (triisopropylsilyl)oxy group at all of the positions of the benzene moiety were synthesized by cyclization of tert-butyl methoxy(or (triisopropylsilyl)oxy)-2-((trimethylsilyl)ethynyl)phenyl)carba- mates with potassium tert-butoxide in tert-butyl alcohol. The (ethynylphenyl)carbamates were synthesized by the palladium-catalyzed reaction of (trimethylsilyl)acetylene and the corresponding (iodophenyl)carbamates, which were selectively synthesized by directed lithiation of the phenylcarbamates and subsequent iodination.

  DOI：

  10.1021/jo970377w
• 作为产物：
  描述：

  3-((triisopropylsilyl)oxy)aniline 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 碘 、 叔丁基锂 作用下， 以 四氢呋喃 、 三乙胺 为溶剂， 反应 146.0h， 生成 (5-Triisopropylsilanyloxy-2-trimethylsilanylethynyl-phenyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  General and Facile Synthesis of Indoles with Oxygen-Bearing Substituents at the Benzene Moiety

  摘要：

  Indoles with oxygen-bearing substituents such as a methoxy or (triisopropylsilyl)oxy group at all of the positions of the benzene moiety were synthesized by cyclization of tert-butyl methoxy(or (triisopropylsilyl)oxy)-2-((trimethylsilyl)ethynyl)phenyl)carba- mates with potassium tert-butoxide in tert-butyl alcohol. The (ethynylphenyl)carbamates were synthesized by the palladium-catalyzed reaction of (trimethylsilyl)acetylene and the corresponding (iodophenyl)carbamates, which were selectively synthesized by directed lithiation of the phenylcarbamates and subsequent iodination.

  DOI：

  10.1021/jo970377w

文献信息

• General and Facile Synthesis of Indoles with Oxygen-Bearing Substituents at the Benzene Moiety
  作者：Yoshinori Kondo、Satoshi Kojima、Takao Sakamoto

  DOI：10.1021/jo970377w

  日期：1997.9.1

  Indoles with oxygen-bearing substituents such as a methoxy or (triisopropylsilyl)oxy group at all of the positions of the benzene moiety were synthesized by cyclization of tert-butyl methoxy(or (triisopropylsilyl)oxy)-2-((trimethylsilyl)ethynyl)phenyl)carba- mates with potassium tert-butoxide in tert-butyl alcohol. The (ethynylphenyl)carbamates were synthesized by the palladium-catalyzed reaction of (trimethylsilyl)acetylene and the corresponding (iodophenyl)carbamates, which were selectively synthesized by directed lithiation of the phenylcarbamates and subsequent iodination.