dihydroquinine

• 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: dihydroquinine
• 英文别名: (R)-[(2S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
• 化学式: C₂₀H₂₆N₂O₂
• 分子量: 326.439
• InChiKey: LJOQGZACKSYWCH-LFDRZELQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  4-乙烯基苯甲酰氯 、 dihydroquinine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以87%的产率得到dihydroquinine 4-vinylbenzoate
  参考文献：
  名称：

  Polymeric cinchona alkaloids for the heterogeneous catalytic asymmetric dihydroxylation of olefins: The influence of the polymer backbone polarity on the compatibility between polymer support and reaction medium

  摘要：

  Heterogeneous catalytic asymmetric dihydroxylation of olefins using homo- and co-polymeric cinchona alkaloids has been reported. The benzoate type homopolymers 2a, b showed high enantioselectivity in the heterogeneous ADH reactions, but their catalytic efficiency was largely dependent on the solvent system which may relate to the accessibility of the active catalytic site. The influence of polymer backbone polarity on the compatibility with the reaction medium was investigated using copolymers 3a, b and 4 having polar polymer backbone. The reaction rates and optical yields were dramatically increased by increasing the polarity of the polymer backbone in NMO-acetone/H2O system.

  DOI：

  10.1016/0957-4166(95)00358-v

文献信息

• Polymeric cinchona alkaloids for the heterogeneous catalytic asymmetric dihydroxylation of olefins: The influence of the polymer backbone polarity on the compatibility between polymer support and reaction medium
  作者：Choong Eui Song、Eun Joo Roh、Sang-gi Lee、In O Kim

  DOI：10.1016/0957-4166(95)00358-v

  日期：1995.11

  Heterogeneous catalytic asymmetric dihydroxylation of olefins using homo- and co-polymeric cinchona alkaloids has been reported. The benzoate type homopolymers 2a, b showed high enantioselectivity in the heterogeneous ADH reactions, but their catalytic efficiency was largely dependent on the solvent system which may relate to the accessibility of the active catalytic site. The influence of polymer backbone polarity on the compatibility with the reaction medium was investigated using copolymers 3a, b and 4 having polar polymer backbone. The reaction rates and optical yields were dramatically increased by increasing the polarity of the polymer backbone in NMO-acetone/H2O system.