| 1399295-93-2

• 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
• CAS: 1399295-93-2
• 化学式: C₁₂H₁₁BrN₄O₂
• 分子量: 323.149
• InChiKey: LUNAWPDCJVQRDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  79.99
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  在 硫化氢铵 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以125 mg的产率得到ethyl 3-amino-5-bromo-1-methyl-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
• 作为产物：
  描述：

  5-溴-1-甲基-1H-吲哚-2-羧酸乙酯 在 sodium azide 、 copper(l) chloride 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 1.08h， 生成
  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