(-)-(R)-2-phenyl-2-(pyridin-2-yloxy)acetic acid | 1196831-44-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(R)-2-phenyl-2-(pyridin-2-yloxy)acetic acid
• 英文别名: (2R)-2-phenyl-2-pyridin-2-yloxyacetic acid
• CAS: 1196831-44-3
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: OGAUEOSXYDKMPX-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-碘吡啶 、 D-扁桃酸 在 copper(l) iodide 、 caesium carbonate 作用下， 以 丁腈 为溶剂， 反应 15.0h， 以41%的产率得到(-)-(R)-2-phenyl-2-(pyridin-2-yloxy)acetic acid
  参考文献：
  名称：

  One-step synthesis of homochiral O-aryl and O-heteroaryl mandelic acids and their use as efficient 1H NMR chiral solvating agents

  摘要：

  Job and Buchwald's one-step copper-promoted arylation of hydroxyl groups was explored and modified so that it could be applied to the coupling of mandelic acid with several halobenzenes and haloheteroarenes. A number of new homochiral O-aryl and O-heteroaryl mandelic acids, generally presenting high enantiomeric purities, were obtained. Although yields were moderate at the best, ranging from 9% to 41%, the reaction was convenient enough to prepare new mandelic acid derivatives, some of which performed as efficient chiral solvating agents (CSAs) for the direct H-1 NMR ee value determination of several clinically and pharmacologically relevant amines. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.002

文献信息

• One-step synthesis of homochiral O-aryl and O-heteroaryl mandelic acids and their use as efficient 1H NMR chiral solvating agents
  作者：Maria Maddalena Cavalluzzi、Claudio Bruno、Giovanni Lentini、Angelo Lovece、Alessia Catalano、Alessia Carocci、Carlo Franchini

  DOI：10.1016/j.tetasy.2009.08.002

  日期：2009.9

  Job and Buchwald's one-step copper-promoted arylation of hydroxyl groups was explored and modified so that it could be applied to the coupling of mandelic acid with several halobenzenes and haloheteroarenes. A number of new homochiral O-aryl and O-heteroaryl mandelic acids, generally presenting high enantiomeric purities, were obtained. Although yields were moderate at the best, ranging from 9% to 41%, the reaction was convenient enough to prepare new mandelic acid derivatives, some of which performed as efficient chiral solvating agents (CSAs) for the direct H-1 NMR ee value determination of several clinically and pharmacologically relevant amines. (C) 2009 Elsevier Ltd. All rights reserved.