2-chloro-3,6-bis(trimethylsilyl)pyridine

• 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-chloro-3,6-bis(trimethylsilyl)pyridine
• 英文别名: (2-Chloro-6-trimethylsilylpyridin-3-yl)-trimethylsilane
• 化学式: C₁₁H₂₀ClNSi₂
• 分子量: 257.91
• InChiKey: WCFVDZJNGSZXLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  三甲基氯硅烷 、 2-chloro-3-deuteriopyridine 在 2,2,6,6-四甲基哌啶 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 以46%的产率得到[2-chloro-(3-²H)-4-pyridyl]trimethylsilane
  参考文献：
  名称：

  Lithiation of 2-Chloro- and 2-Methoxypyridine with Lithium Dialkylamides: Initial Ortho-Direction or Subsequent Lithium Ortho-Stabilization?

  摘要：

  The lithiation pathway of 2-chloro and 2-methoxypyridine with LDA and LTMP has been investigated using deuterated probes. The availability of both H-6 and H-3 protons on the pyridine nucleus was found to be critical to ensure complete C-3 lithiation. We thus concluded that the C-3 lithiation was not a straightforward process. A mechanism involving precomplexation of lithium dialkylamides near the H-6 proton and formation of a 3,6-dilithio pyridine intermediate is proposed.

  DOI：

  10.1021/jo026559u

文献信息

• Lithiation of 2-Chloro- and 2-Methoxypyridine with Lithium Dialkylamides: Initial Ortho-Direction or Subsequent Lithium Ortho-Stabilization?
  作者：Philippe Gros、Sabine Choppin、Yves Fort

  DOI：10.1021/jo026559u

  日期：2003.3.1

  The lithiation pathway of 2-chloro and 2-methoxypyridine with LDA and LTMP has been investigated using deuterated probes. The availability of both H-6 and H-3 protons on the pyridine nucleus was found to be critical to ensure complete C-3 lithiation. We thus concluded that the C-3 lithiation was not a straightforward process. A mechanism involving precomplexation of lithium dialkylamides near the H-6 proton and formation of a 3,6-dilithio pyridine intermediate is proposed.