O-propionylquinidine

• 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: O-propionylquinidine
• 英文别名: [(S)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methyl] propanoate
• 化学式: C₂₃H₂₈N₂O₃
• 分子量: 380.487
• InChiKey: GWLWQRRMIMIZSS-BAHGIXHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  51.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  O-propionylquinidine 在 三溴化硼 、 氨 、 水 作用下， 以 二氯甲烷 为溶剂， 以50%的产率得到(S)-(6-hydroxyquinolin-4-yl)((2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl propionate
  参考文献：
  名称：

  Enantioselective Michael reaction of nitroalkanes onto nitroalkenes catalyzed by cinchona alkaloid derivatives

  摘要：

  An effective asymmetric synthesis of optically active 1,3-dinitro compounds via the direct Michael addition of nitroalkanes onto nitroalkenes has been described. In the presence of readily modified cinchona alkaloid derivatives, nitroethane reacted well with a variety of aromatic and heterocyclic aromatic nitroalkenes to afford products with good diastereoselectivities (dr up to 72/28) and enantioselectivities (ee up to 94%). The catalyst loading can be decreased to 2 mol % without compromising the asymmetric induction or the reaction rate. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.11.008

文献信息

• Enantioselective Michael reaction of nitroalkanes onto nitroalkenes catalyzed by cinchona alkaloid derivatives
  作者：Yan-Qiu Deng、Zhen-Wei Zhang、Ya-Hui Feng、Albert S.C. Chan、Gui Lu

  DOI：10.1016/j.tetasy.2012.11.008

  日期：2012.12

  An effective asymmetric synthesis of optically active 1,3-dinitro compounds via the direct Michael addition of nitroalkanes onto nitroalkenes has been described. In the presence of readily modified cinchona alkaloid derivatives, nitroethane reacted well with a variety of aromatic and heterocyclic aromatic nitroalkenes to afford products with good diastereoselectivities (dr up to 72/28) and enantioselectivities (ee up to 94%). The catalyst loading can be decreased to 2 mol % without compromising the asymmetric induction or the reaction rate. (C) 2012 Elsevier Ltd. All rights reserved.