(S)-(-)-1,2,2,2-Tetrafluoroethyl (R,S)-chlorofluoromethyl ether | 1933757-76-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: (S)-(-)-1,2,2,2-Tetrafluoroethyl (R,S)-chlorofluoromethyl ether
• 英文别名: (2S)-2-[Chloro(fluoro)methoxy]-1,1,1,2-tetrafluoroethane
• CAS: 1933757-76-6
• 化学式: C₃H₂ClF₅O
• 分子量: 184.493
• InChiKey: GGEBMRHBGQLKGJ-ZILXKATJSA-N

物化性质

• 沸点：
  65.6±35.0 °C(Predicted)
• 密度：
  1.489±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (S)-(-)-1,2,2,2-Tetrafluoroethyl dichlorofluoromethyl ether 在 异丙醇 作用下， 反应 4.0h， 以47%的产率得到(S)-(-)-1,2,2,2-Tetrafluoroethyl (R,S)-chlorofluoromethyl ether
  参考文献：
  名称：

  Asymmetric Synthesis of the Volatile Anesthetic 1,2,2,2-Tetrafluoroethyl Chlorofluoromethyl Ether Using a Stereospecific Decarboxylation of Unusual Stereochemical Outcome

  摘要：

  Acid 1 is optically resolved by diastereomeric amide formation/chromatography/hydrolysis. Decarboxylation of the enantiomers of acid 1 gives the enantiomers of ether 2 with a very high degree of stereospecificity. The absolute configurations of both the starting acid and the ether product are determined to be (R)-(+) and(S)-(-). The data indicate that decarboxylation occurs with clean inversion of configuration. A mechanism is proposed to rationalize this. unusual result. The enantiomers of ether 2 are converted to diastereomers of the volatile anesthetic 3 by a route consisting of trichlorination of the methyl group to give 9, monofluorination to yield 10, and monoreduction to afford the target anesthetic.

  DOI：

  10.1021/jo00110a041