2-[(trimethylsilanyl)ethynyl]-2H-pyridine-1-carboxylic acid ethyl ester | 176096-29-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-[(trimethylsilanyl)ethynyl]-2H-pyridine-1-carboxylic acid ethyl ester
• 英文别名: ethyl 2-(2-trimethylsilylethynyl)-2H-pyridine-1-carboxylate
• CAS: 176096-29-0
• 化学式: C₁₃H₁₉NO₂Si
• 分子量: 249.385
• InChiKey: IRVVNDPSKDAZQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  吡啶 、 氯甲酸乙酯 、 三甲基乙炔基硅 在 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以72%的产率得到2-[(trimethylsilanyl)ethynyl]-2H-pyridine-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  Copper-Catalyzed Coupling of Pyridines and Quinolines with Alkynes:  A One-Step, Asymmetric Route to Functionalized Heterocycles

  摘要：

  [GRAPHICS]A copper (I)-catalyzed, asymmetric method to directly functionalize pyridines, quinolines, and isoquinolines with terminal alkynes is described. The reaction is readily diversified to incorporate a range of pyridine-based heterocycles and electron-rich or electron-poor alkynes. This provides a straightforward alternative to nucleophilic or cross-coupling approaches to directly derivatize these heterocycles, and yields useful propargylcarbamates.

  DOI：

  10.1021/jo702293h

文献信息

• Copper-Catalyzed Coupling of Pyridines and Quinolines with Alkynes:  A One-Step, Asymmetric Route to Functionalized Heterocycles
  作者：Daniel A. Black、Ramsay E. Beveridge、Bruce A. Arndtsen

  DOI：10.1021/jo702293h

  日期：2008.3.1

  [GRAPHICS]A copper (I)-catalyzed, asymmetric method to directly functionalize pyridines, quinolines, and isoquinolines with terminal alkynes is described. The reaction is readily diversified to incorporate a range of pyridine-based heterocycles and electron-rich or electron-poor alkynes. This provides a straightforward alternative to nucleophilic or cross-coupling approaches to directly derivatize these heterocycles, and yields useful propargylcarbamates.