[6-chloro-(5-²H)-2-pyridyl]trimethylsilane

• 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: [6-chloro-(5-²H)-2-pyridyl]trimethylsilane
• 英文别名: 2-chloro[3-2H]-6-pyridyl(trimethyl)silane；(6-Chloro-5-deuteriopyridin-2-yl)-trimethylsilane
• 化学式: C₈H₁₂ClNSi
• 分子量: 186.721
• InChiKey: HZVILOHLHGUUHU-UICOGKGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  2-氯吡啶 在 正丁基锂 、 N,N-二甲基乙醇胺 、 2,2,6,6-tetramethylpiperidinyl-lithium 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.5h， 生成 [6-chloro-(5-²H)-2-pyridyl]trimethylsilane
  参考文献：
  名称：

  Lithiation of 2-Heterosubstituted Pyridines with BuLi−LiDMAE:  Evidence for Regiospecificity at C-6

  摘要：

  The determination of the initial deprotonation site of 2-chloro- and 2-methoxypyridine during reaction with BuLi-LiDMAE has been investigated. A series of experiments on deuterated regioisomers revealed a direct lithiation at C-6 excluding a potential first classical ortholithiation and lithium equilibration in the reaction medium. These results suggested that the formation of lithium aggregates at the neighboring of the pyridinic nitrogen atom favored BuLi delivery at C-6 as well as 6-lithio intermediate stabilization.

  DOI：

  10.1021/jo015855o

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.
• Lithiation of 2-Heterosubstituted Pyridines with BuLi−LiDMAE:  Evidence for Regiospecificity at C-6
  作者：Philippe Gros、Sabine Choppin、Julien Mathieu、Yves Fort

  DOI：10.1021/jo015855o

  日期：2002.1.1

  The determination of the initial deprotonation site of 2-chloro- and 2-methoxypyridine during reaction with BuLi-LiDMAE has been investigated. A series of experiments on deuterated regioisomers revealed a direct lithiation at C-6 excluding a potential first classical ortholithiation and lithium equilibration in the reaction medium. These results suggested that the formation of lithium aggregates at the neighboring of the pyridinic nitrogen atom favored BuLi delivery at C-6 as well as 6-lithio intermediate stabilization.