(S)-(-)-1,2,2,2-Tetrafluoroethyl methyl ether | 156700-89-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-(-)-1,2,2,2-Tetrafluoroethyl methyl ether
• 英文别名: (S)-(-)-1,2,2,2-Tetrafluorethylmethylether；Ethane, 1,1,1,2-tetrafluoro-2-methoxy-, (S)-；(2S)-1,1,1,2-tetrafluoro-2-methoxyethane
• CAS: 156700-89-9
• 化学式: C₃H₄F₄O
• 分子量: 132.058
• InChiKey: BEPCUGVFWAYLBF-UWTATZPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  8
• 可旋转键数：
  1
• 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：
  5

反应信息

• 作为反应物：
  描述：

  (S)-(-)-1,2,2,2-Tetrafluoroethyl methyl ether 在 溴 、 三氟化锑 、 氯 作用下， 生成 (S)-(-)-1,2,2,2-Tetrafluoroethyl chlorodifluoromethyl ether
  参考文献：
  名称：

  Ramig, Keith; Brockunier, Linda; Rafalko, Patrice W., Angewandte Chemie, 1995, vol. 107, # 2, p. 254 - 255

  摘要：

  DOI：
• 作为产物：
  描述：

  (+)-(R)-1-Methoxytetrafluorpropionsaeure 在 N,N-二甲基丙烯基脲 、 氢氧化钾 、 三乙二醇 作用下， 以70%的产率得到(S)-(-)-1,2,2,2-Tetrafluoroethyl methyl 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

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.
• 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：——