(S)-(-)-Desflurane | 142916-68-5

• 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)-(-)-Desflurane
• 英文别名: (2S)-2-(difluoromethoxy)-1,1,1,2-tetrafluoroethane
• CAS: 142916-68-5
• 化学式: C₃H₂F₆O
• 分子量: 168.039
• InChiKey: DPYMFVXJLLWWEU-PVQJCKRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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：
  7

反应信息

• 作为产物：
  描述：

  (S)-(-)-1,2,2,2-Tetrafluoroethyl chlorodifluoromethyl ether 在 sodium 、 氯化铵 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (S)-(-)-Desflurane
  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

文献信息

• Asymmetric Synthesis of the Volatile Anesthetic 1,2,2,2-Tetrafluoroethyl Chlorofluoromethyl Ether Using a Stereospecific Decarboxylation of Unusual Stereochemical Outcome
  作者：Leonid A. Rozov、Patrice W. Rafalko、Suzanne M. Evans、Linda Brockunier、Keith Ramig

  DOI：10.1021/jo00110a041

  日期：1995.3

  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.
• Enantioselective synthesis of the volatile anesthetic desflurane
  作者：Leonid A. Rozov、Chialang G. Huang、Donald F. Halpern、Gerald G. Vernice、Keith Ramig

  DOI：10.1016/s0957-4166(97)00382-0

  日期：1997.9

  The first enantioselective synthesis of the commercial volatile anesthetic desflurane is reported. Treatment of (R)-(-)-isoflurane with BrF3 gives (S)-(+)-desflurane with >96% inversion of configuration. This constitutes a correction of previously reported results. (C) 1997 Elsevier Science Ltd.
• Ramig, Keith; Brockunier, Linda; Rafalko, Patrice W., Angewandte Chemie, 1995, vol. 107, # 2, p. 254 - 255
  作者：Ramig, Keith、Brockunier, Linda、Rafalko, Patrice W.、Rozov, Leonid A.

  DOI：——

  日期：——