1-(2-bromopyridin-3-yl)cyclohexanol | 780801-09-4

• 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: 1-(2-bromopyridin-3-yl)cyclohexanol
• 英文别名: 1-(2-Bromopyridin-3-yl)cyclohexan-1-ol
• CAS: 780801-09-4
• 化学式: C₁₁H₁₄BrNO
• 分子量: 256.142
• InChiKey: SRFPBPKLLFLQEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-bromopyridin-3-yl)cyclohexanol 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 85.0 ℃ 、4.0 MPa 条件下， 反应 64.0h， 以74%的产率得到3-cyclohexylpiperidine
  参考文献：
  名称：

  Approach to 3-(Cyclo)alkylpiperidines through ‘sp3–sp3 via sp2–sp3’ Coupling

  摘要：

  The idea of introducing (cyclo)alkyl substituents at the C-3 atom of the piperidine ring, that is, formal sp(3)-sp(3) retrosynthetic disconnection, is implemented through a two-step reaction sequence including directed ortho metalation of a pyridine derivative and the subsequent quenching with a carbonyl compound, followed by catalytic hydrogenation. This robust but very efficient method allows for multigram preparation of sp(3)-rich 3-(cyclo)alkylpiperidines, which are valuable building blocks for medicinal chemistry and other areas.

  DOI：

  10.1055/s-0034-1379502
• 作为产物：
  描述：

  2-溴吡啶 、 环己酮 在 正丁基锂 、 二异丙胺 、 水 、 碳酸氢钠 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.16h， 以54%的产率得到1-(2-bromopyridin-3-yl)cyclohexanol
  参考文献：
  名称：

  Approach to 3-(Cyclo)alkylpiperidines through ‘sp3–sp3 via sp2–sp3’ Coupling

  摘要：

  The idea of introducing (cyclo)alkyl substituents at the C-3 atom of the piperidine ring, that is, formal sp(3)-sp(3) retrosynthetic disconnection, is implemented through a two-step reaction sequence including directed ortho metalation of a pyridine derivative and the subsequent quenching with a carbonyl compound, followed by catalytic hydrogenation. This robust but very efficient method allows for multigram preparation of sp(3)-rich 3-(cyclo)alkylpiperidines, which are valuable building blocks for medicinal chemistry and other areas.

  DOI：

  10.1055/s-0034-1379502