ethyl 3-amino-5-bromo-1-[2-(trimethylsilyl)ethoxymethyl]-1H-indole-2-carboxylate | 1399297-74-5

• 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: ethyl 3-amino-5-bromo-1-[2-(trimethylsilyl)ethoxymethyl]-1H-indole-2-carboxylate
• 英文别名: Ethyl 3-amino-5-bromo-1-(2-trimethylsilylethoxymethyl)indole-2-carboxylate；ethyl 3-amino-5-bromo-1-(2-trimethylsilylethoxymethyl)indole-2-carboxylate
• CAS: 1399297-74-5
• 化学式: C₁₇H₂₅BrN₂O₃Si
• 分子量: 413.387
• InChiKey: QLQXZUPGWTULPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 硫化氢铵 、 copper(l) chloride 作用下， 以 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 1.0h， 生成 ethyl 3-amino-5-bromo-1-[2-(trimethylsilyl)ethoxymethyl]-1H-indole-2-carboxylate
  参考文献：
  名称：

  Indirect C–H Azidation of Heterocycles via Copper-Catalyzed Regioselective Fragmentation of Unsymmetrical λ³-Iodanes

  摘要：

  A C-H bond of electron-rich heterocycles is transformed into a C-N bond in a reaction sequence comprising the formation of heteroaryl(phenyl)iodonium azides and their in situ regioselective fragmentation to heteroaryl azides. A Cu(I) catalyst ensures complete regiocontrol in the fragmentation step and catalyzes the subsequent 1,3-dipolar cycloaddition of the formed azido heterocycles with acetylenes. The heteroaryl azides can also be conveniently reduced to heteroarylamines by aqueous ammonium sulfide. The overall C-H to C-N transformation is a mild and operationally simple one-pot sequential multistep process.

  DOI：

  10.1021/ja305574k

文献信息

• Indirect C–H Azidation of Heterocycles via Copper-Catalyzed Regioselective Fragmentation of Unsymmetrical λ³-Iodanes
  作者：Dmitrijs Lubriks、Igors Sokolovs、Edgars Suna

  DOI：10.1021/ja305574k

  日期：2012.9.19

  A C-H bond of electron-rich heterocycles is transformed into a C-N bond in a reaction sequence comprising the formation of heteroaryl(phenyl)iodonium azides and their in situ regioselective fragmentation to heteroaryl azides. A Cu(I) catalyst ensures complete regiocontrol in the fragmentation step and catalyzes the subsequent 1,3-dipolar cycloaddition of the formed azido heterocycles with acetylenes. The heteroaryl azides can also be conveniently reduced to heteroarylamines by aqueous ammonium sulfide. The overall C-H to C-N transformation is a mild and operationally simple one-pot sequential multistep process.