| 142796-69-8

• CAS: 142796-69-8
• 化学式: C₁₀H₁₇NO₃
• 分子量: 200.242
• InChiKey: QIQNNBXHAYSQRY-NUXSFZQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.0
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  49.77
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  methyl (1R,2S,3S,5S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate 在 氘代甲醇-d 、 sodium methylate 作用下， 反应 240.0h， 以47%的产率得到
  参考文献：
  名称：

  Base-catalyzed C-2 exchange and epimerization of cocaine analogs: methyl 3.beta.-substituted 8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylates

  摘要：

  The kinetic and thermodynamic parameters associated with epimeric 2-carbomethoxy-3-beta-substituted tropanes have been investigated by means of base-catalyzed deuterium incorporation, epimerization, and by molecular modeling. The equilibration results, as well as the molecular mechanics calculations, showed the 2-alpha-epimers to be more stable than the 2-beta-epimers. However, it was found that the energies of the transitions states for deprotonation at C-2 from the beta-face were higher than those for deprotonation from the alpha-face. These results are contrary to what would have been predicted based on the assumption that the more exothermic reaction pathway would involve a more stabilized transition state.

  DOI：

  10.1021/jo00044a028