3-ethoxy-2-(quinolin-4-yl)-6-vinyl-1-azabicyclo[3.2.2]nonane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-ethoxy-2-(quinolin-4-yl)-6-vinyl-1-azabicyclo[3.2.2]nonane
• 英文别名: 4-[(2S,3R,5S,6R)-6-ethenyl-3-ethoxy-1-azabicyclo[3.2.2]nonan-2-yl]quinoline
• 化学式: C₂₁H₂₆N₂O
• 分子量: 322.45
• InChiKey: FXVRRBFHMDEXRW-AFMUBRCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  25.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  辛可尼丁 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 87.0h， 生成 3-ethoxy-2-(quinolin-4-yl)-6-vinyl-1-azabicyclo[3.2.2]nonane
  参考文献：
  名称：

  Preparation of Enantiopure 1-Azabicyclo[3.2.2]nonanes Functionalized at Carbon C3, from Cinchonine and Cinchonidine. Stereoselective Solvolysis and an Easily Enolizable Ketone

  摘要：

  Solvolysis of C9 mesylated cinchonidine 1-OMs and cinchonine 2-OMs in solvent MeOH, EtOH, and CF3CH2OH affords ring-expanded 1-azabicyclo[3.2.2]nonanes oxygenated at carbon C3 ("second Cinchona rearrangement"). The newly introduced substituents at C3 and the neighboring quinolyl group Q' at C2 adopt quasiequatorial positions. The derived 1-azabicyclo[3.2.2]nonan-3-ones 5 and 6 are easily equilibrated. On contact with MeOD uptake of deuterium takes place at room temperature.

  DOI：

  10.1021/jo026890d

文献信息

• Preparation of Enantiopure 1-Azabicyclo[3.2.2]nonanes Functionalized at Carbon C3, from Cinchonine and Cinchonidine. Stereoselective Solvolysis and an Easily Enolizable Ketone
  作者：Stefanie Röper、M. Heiko Franz、Rudolf Wartchow、H. Martin R. Hoffmann

  DOI：10.1021/jo026890d

  日期：2003.6.1

  Solvolysis of C9 mesylated cinchonidine 1-OMs and cinchonine 2-OMs in solvent MeOH, EtOH, and CF3CH2OH affords ring-expanded 1-azabicyclo[3.2.2]nonanes oxygenated at carbon C3 ("second Cinchona rearrangement"). The newly introduced substituents at C3 and the neighboring quinolyl group Q' at C2 adopt quasiequatorial positions. The derived 1-azabicyclo[3.2.2]nonan-3-ones 5 and 6 are easily equilibrated. On contact with MeOD uptake of deuterium takes place at room temperature.