2-(2-trimethylsilylethynyl)-3-methylthiopyridine | 900535-84-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(2-trimethylsilylethynyl)-3-methylthiopyridine
• 英文别名: Trimethyl-[2-(3-methylsulfanylpyridin-2-yl)ethynyl]silane
• CAS: 900535-84-4
• 化学式: C₁₁H₁₅NSSi
• 分子量: 221.398
• InChiKey: WKQSRMUGQYRSAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-trimethylsilylethynyl)-3-methylthiopyridine 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以42%的产率得到3-bromo-2-trimethylsilylthieno[3,2-b]pyridine
  参考文献：
  名称：

  New efficient access to thieno[3,2-b]pyridine derivatives via regioselective lithiation of 3-methylthiopyridine

  摘要：

  The synthesis of thieno[3,2-b]pyridines was achieved using a three-step process allowing the construction of the thiophenic ring with 17-34% overall yields. The key step was the regioselective lithiation-bromination of the 3-methylthiopyridine induced by BuLi-LiDMAE superbase followed by Sonogashira coupling and halogenocyclization producing the fused heterocycles. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.008
• 作为产物：
  描述：

  3-(甲基硫代)吡啶 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 正丁基锂 、 N,N-二甲基乙醇胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 20.0h， 生成 2-(2-trimethylsilylethynyl)-3-methylthiopyridine
  参考文献：
  名称：

  New efficient access to thieno[3,2-b]pyridine derivatives via regioselective lithiation of 3-methylthiopyridine

  摘要：

  The synthesis of thieno[3,2-b]pyridines was achieved using a three-step process allowing the construction of the thiophenic ring with 17-34% overall yields. The key step was the regioselective lithiation-bromination of the 3-methylthiopyridine induced by BuLi-LiDMAE superbase followed by Sonogashira coupling and halogenocyclization producing the fused heterocycles. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.008

文献信息

• New efficient access to thieno[3,2-b]pyridine derivatives via regioselective lithiation of 3-methylthiopyridine
  作者：Corinne Comoy、Estelle Banaszak、Yves Fort

  DOI：10.1016/j.tet.2006.04.008

  日期：2006.6

  The synthesis of thieno[3,2-b]pyridines was achieved using a three-step process allowing the construction of the thiophenic ring with 17-34% overall yields. The key step was the regioselective lithiation-bromination of the 3-methylthiopyridine induced by BuLi-LiDMAE superbase followed by Sonogashira coupling and halogenocyclization producing the fused heterocycles. (c) 2006 Elsevier Ltd. All rights reserved.