Quinine

• 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: Quinine
• 英文别名: (R)-[(2S,5S)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
• 化学式: C₂₀H₂₄N₂O₂
• 分子量: 324.423
• InChiKey: LOUPRKONTZGTKE-WTLRTRQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  45.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Quinine 在 Rh/Al₂O₃ 盐酸 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以72%的产率得到(E)-R-[(2S,4S,)-5-ethylidenequinuclidin-2-yl](6methoxyquinolin-4-yl)methanol
  参考文献：
  名称：

  Positional isomerization of quinine and quinidine via rhodium on alumina catalysis: practical one-step synthesis of Δ3,10-isoquinine and Δ3,10-isoquinidine

  摘要：

  The synthesis of Delta(3,10)-isoquinine (5Z,5E) and Delta(3,10)-isoquinidine (6Z,6E) was achieved in one-step through positional isomerization of the terminal alkene in the parent cinchona alkaloids using catalytic amounts of 5% Rh/Al2O3 and excess hydrochloric acid in refluxing 50% aqueous EtOH. The products were obtained in good yields as a mixture of E and Z geometric isomers and fully characterized using spectroscopic methods. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01180-8

文献信息

• Positional isomerization of quinine and quinidine via rhodium on alumina catalysis: practical one-step synthesis of Δ3,10-isoquinine and Δ3,10-isoquinidine
  作者：David E Portlock、Dinabandhu Naskar、Laura West、William L Seibel、Titan Gu、Howard J Krauss、X.Sean Peng、Paul M Dybas、Edward G Soyke、Stephen B Ashton、Jonathan Burton

  DOI：10.1016/s0040-4039(03)01180-8

  日期：2003.7

  The synthesis of Delta(3,10)-isoquinine (5Z,5E) and Delta(3,10)-isoquinidine (6Z,6E) was achieved in one-step through positional isomerization of the terminal alkene in the parent cinchona alkaloids using catalytic amounts of 5% Rh/Al2O3 and excess hydrochloric acid in refluxing 50% aqueous EtOH. The products were obtained in good yields as a mixture of E and Z geometric isomers and fully characterized using spectroscopic methods. (C) 2003 Elsevier Science Ltd. All rights reserved.