(+)-(S)-2-(2,3,4,5,6-pentafluorophenoxy)-2-(phenyl-d₅)acetic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+)-(S)-2-(2,3,4,5,6-pentafluorophenoxy)-2-(phenyl-d₅)acetic acid
• 英文别名: (+)-(S)-O-pentafluorophenyl mandelic acid-d₅；(2S)-2-(2,3,4,5,6-pentadeuteriophenyl)-2-(2,3,4,5,6-pentafluorophenoxy)acetic acid
• 化学式: C₁₄H₇F₅O₃
• 分子量: 323.16
• InChiKey: FOYPKWRFUOPTDC-SZKCUTCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  氘代苯 在 盐酸 、 aluminum (III) chloride 、 copper(l) iodide 、 水 、 caesium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 24.31h， 生成 (+)-(S)-2-(2,3,4,5,6-pentafluorophenoxy)-2-(phenyl-d₅)acetic acid
  参考文献：
  名称：

  Preparation of (−)-(R)-2-(2,3,4,5,6-pentafluorophenoxy)-2-(phenyl-d5)acetic acid: an efficient 1H NMR chiral solvating agent for direct enantiomeric purity evaluation of quinoline-containing antimalarial drugs

  摘要：

  The title compound was prepared as a racemate from (+/-)-mandelic acid-d(5) in one step. The corresponding (-)-(R)-enantiomer (98% ee) was obtained by resolution with (-)-(R)-1-phenylethylamine and evaluated as a chiral solvating agent (CSA) for direct H-1 NMR enantiomeric excess determination of mefloquine (Lariam (R), chloroquine (Chloroquine Bayer (R)), and hydroxychloroquine (Plaquenil (R)) enantiomers. The displayed non-equivalence was high for signals in the aromatic region of all three antimalarials. Thus, the mandelic acid derivative described herein may be considered as the first efficient CSA 'invisible' in the aromatic region, useful for direct H-1 NMR ee value determination of chiral quinoline-containing antimalarial drugs. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.11.007

文献信息

• Preparation of (−)-(R)-2-(2,3,4,5,6-pentafluorophenoxy)-2-(phenyl-d5)acetic acid: an efficient 1H NMR chiral solvating agent for direct enantiomeric purity evaluation of quinoline-containing antimalarial drugs
  作者：Maria Maddalena Cavalluzzi、Angelo Lovece、Claudio Bruno、Carlo Franchini、Giovanni Lentini

  DOI：10.1016/j.tetasy.2014.11.007

  日期：2014.12

  The title compound was prepared as a racemate from (+/-)-mandelic acid-d(5) in one step. The corresponding (-)-(R)-enantiomer (98% ee) was obtained by resolution with (-)-(R)-1-phenylethylamine and evaluated as a chiral solvating agent (CSA) for direct H-1 NMR enantiomeric excess determination of mefloquine (Lariam (R), chloroquine (Chloroquine Bayer (R)), and hydroxychloroquine (Plaquenil (R)) enantiomers. The displayed non-equivalence was high for signals in the aromatic region of all three antimalarials. Thus, the mandelic acid derivative described herein may be considered as the first efficient CSA 'invisible' in the aromatic region, useful for direct H-1 NMR ee value determination of chiral quinoline-containing antimalarial drugs. (C) 2014 Elsevier Ltd. All rights reserved.