(R)-(+)-1-Methoxy-1,2,2,2-tetrafuoropropionic acid (S)-(-)-1-phenethylamide | 156700-92-4

• 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: (R)-(+)-1-Methoxy-1,2,2,2-tetrafuoropropionic acid (S)-(-)-1-phenethylamide
• 英文别名: (2R)-2,3,3,3-tetrafluoro-2-methoxy-N-[(1S)-1-phenylethyl]propanamide
• CAS: 156700-92-4
• 化学式: C₁₂H₁₃F₄NO₂
• 分子量: 279.234
• InChiKey: FJECLEFTKYQIRR-KWQFWETISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-(+)-1-Methoxy-1,2,2,2-tetrafuoropropionic acid (S)-(-)-1-phenethylamide 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 19.5h， 以64%的产率得到N-(S)-1-Phenethyl-(R)-2,3,3,3-tetrafluoro-2-methoxypropylamine
  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
• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 、 (+/-)-1-Methoxytetrafluoropropionyl chloride 在 吡啶 作用下， 以 乙醚 为溶剂， 反应 4.0h， 生成 (S)-(-)-1-Methoxy-1,2,2,2-tetrafuoropropionic acid (S)-(-)-1-phenethylamide 、 (R)-(+)-1-Methoxy-1,2,2,2-tetrafuoropropionic acid (S)-(-)-1-phenethylamide
  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

• 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：——
• 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.