(3S)-3-hydroxyquinine 9-acetate | 859458-69-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 金鸡纳生物碱
• 英文名称: (3S)-3-hydroxyquinine 9-acetate
• 英文别名: [(R)-[(2S,4S,5S)-5-ethenyl-5-hydroxy-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methyl] acetate
• CAS: 859458-69-8
• 化学式: C₂₂H₂₆N₂O₄
• 分子量: 382.459
• InChiKey: SDPMGNAXMMRORO-DSAKXZLESA-N

物化性质

• 沸点：
  531.1±50.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  71.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S)-3-hydroxyquinine 9-acetate 在 甲醇 、 potassium carbonate 作用下， 反应 3.0h， 以90%的产率得到3-羟基奎宁
  参考文献：
  名称：

  Confirmation of the Structure of (3S)-3-Hydroxyquinine:  Synthesis and X-ray Crystal Structure of Its 9-Aceto Analogue

  摘要：

  3(S)-3-Hydroxyquinine (2) has been separated from its epimeric mixture at C-3 by conversion into the 9-aceto analogue followed by chromatography. The molecular structure of the acetate was determined through single-crystal X-ray analysis, and this confirms the structure of (3S)-3-hydroxyquinine (2), the major metabolite of quinine (1).

  DOI：

  10.1021/np050015g
• 作为产物：
  描述：

  3-hydroxyquinine 、 乙酸酐 在 吡啶 作用下， 反应 3.0h， 以75%的产率得到(3S)-3-hydroxyquinine 9-acetate
  参考文献：
  名称：

  Confirmation of the Structure of (3S)-3-Hydroxyquinine:  Synthesis and X-ray Crystal Structure of Its 9-Aceto Analogue

  摘要：

  3(S)-3-Hydroxyquinine (2) has been separated from its epimeric mixture at C-3 by conversion into the 9-aceto analogue followed by chromatography. The molecular structure of the acetate was determined through single-crystal X-ray analysis, and this confirms the structure of (3S)-3-hydroxyquinine (2), the major metabolite of quinine (1).

  DOI：

  10.1021/np050015g