2,6-dilithiopyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环化合物
• 英文名称: 2,6-dilithiopyridine
• 化学式: C₅H₃Li₂N
• 分子量: 90.9675
• InChiKey: MRMFCNSLTLKBQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.96
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,6-dilithiopyridine 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 6-溴吡啶-2-甲醛
  参考文献：
  名称：

  A study of the lithiation of 2,6-dibromopyridine with butyllithium, and its application to synthesis of L-739,010

  摘要：

  Mono-lithiation of 2,6-dibromopyridine by n-BuLi is complicated by deprotonation of the pyridine ring by the resulting mono-lithium species. This problem can be eliminated by a reverse addition, but this causes formation of the undesired dilithio species. However, rapid lithium-halogen exchange between 2,6-dibromopyridine and 2,6-dilithiopyridine produces 2-brom-6-lithiopyridine cleanly. Thus, using reverse addition, the mono-lithiated pyridine can be generated in 98% yield. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0040-4039(96)00336-x
• 作为产物：
  描述：

  2,6-二溴吡啶 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 正溴丁烷 、 2,6-dilithiopyridine
  参考文献：
  名称：

  A study of the lithiation of 2,6-dibromopyridine with butyllithium, and its application to synthesis of L-739,010

  摘要：

  Mono-lithiation of 2,6-dibromopyridine by n-BuLi is complicated by deprotonation of the pyridine ring by the resulting mono-lithium species. This problem can be eliminated by a reverse addition, but this causes formation of the undesired dilithio species. However, rapid lithium-halogen exchange between 2,6-dibromopyridine and 2,6-dilithiopyridine produces 2-brom-6-lithiopyridine cleanly. Thus, using reverse addition, the mono-lithiated pyridine can be generated in 98% yield. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0040-4039(96)00336-x

文献信息

• A study of the lithiation of 2,6-dibromopyridine with butyllithium, and its application to synthesis of L-739,010
  作者：Dongwei Cai、David L. Hughes、Thomas R. Verhoeven

  DOI：10.1016/0040-4039(96)00336-x

  日期：1996.4

  Mono-lithiation of 2,6-dibromopyridine by n-BuLi is complicated by deprotonation of the pyridine ring by the resulting mono-lithium species. This problem can be eliminated by a reverse addition, but this causes formation of the undesired dilithio species. However, rapid lithium-halogen exchange between 2,6-dibromopyridine and 2,6-dilithiopyridine produces 2-brom-6-lithiopyridine cleanly. Thus, using reverse addition, the mono-lithiated pyridine can be generated in 98% yield. Copyright (C) 1996 Elsevier Science Ltd