O-acetylquinidine | 849094-81-1

• 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-acetylquinidine
• 英文别名: [(S)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methyl] acetate
• CAS: 849094-81-1
• 化学式: C₂₂H₂₆N₂O₃
• 分子量: 366.46
• InChiKey: LBXIBQQYUBUMMK-QDGJQWLKSA-N

物化性质

• 沸点：
  496.2±40.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 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：
  51.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  O-acetylquinidine 在 三溴化硼 、 氨 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以70%的产率得到(S)-(6-hydroxyquinolin-4-yl)((2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl acetate
  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

• Reaction of quinine, 9-epiquinine and their acetates in superacid in the presence of hydrogen peroxide: an access to new fluorhydrins and/or ketones
  作者：Vincent Chagnault、Marie-Paule Jouannetaud、Jean-Claude Jacquesy

  DOI：10.1016/j.tetlet.2006.06.011

  日期：2006.8

  In HF-SbF5, in the presence of H2O2 (Source of OH+ equivalent) quinine la yields 10-keto derivatives 4a and 5a and cyclic ether 3 as the major product. In the same conditions 1b, 2a, and 2b give the 10-keto and 10-fluoro-3-hydroxy analogs. (c) 2006 Elsevier Ltd. All rights reserved.