(S)-3-(((Benzyloxy)carbonyl)amino)-4,4,4-trifluorobutanoic acid | 1458674-47-9

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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)-3-(((Benzyloxy)carbonyl)amino)-4,4,4-trifluorobutanoic acid
• 英文别名: (3S)-4,4,4-trifluoro-3-(phenylmethoxycarbonylamino)butanoic acid
• CAS: 1458674-47-9
• 化学式: C₁₂H₁₂F₃NO₄
• 分子量: 291.227
• InChiKey: OMSAXGBLDRPUIP-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  L-丙氨酸乙酯 、 (S)-3-(((Benzyloxy)carbonyl)amino)-4,4,4-trifluorobutanoic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以84%的产率得到ethyl (2S)-2-[[(3S)-4,4,4-trifluoro-3-(phenylmethoxycarbonylamino)butanoyl]amino]propanoate
  参考文献：
  名称：

  Stereo-regulated synthesis of peptides containing a β-trifluoromethyl-β-amino acid

  摘要：

  For the chemical conversions of a beta-trifluoromethyl-beta-amino acid ((S)-4,4,4-trifluoro-3-aminobutyric acid, 1), such as the N-terminus protection with benzyloxycarbonyl or tert-butoxycarbonyl group, the C-terminus protection with benzyl or tert-butyl group, and peptide elongation at the both termini, highly practical protocols were established. Through these conversions, the stereochemistry of 1 and/or its condensation counterpart was maintained. Because the protocols developed here are indispensable for the application of 1 in peptide engineering, they would expand the utility of 1 and its derivatives. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.051
• 作为产物：
  描述：

  ethyl (S)-3-(((benzyloxy)carbonyl)amino)-4,4,4-trifluorobutanoate 在 lithium hydroxide monohydrate 、 水 作用下， 以 1,4-二氧六环 为溶剂， 以91%的产率得到(S)-3-(((Benzyloxy)carbonyl)amino)-4,4,4-trifluorobutanoic acid
  参考文献：
  名称：

  Stereo-regulated synthesis of peptides containing a β-trifluoromethyl-β-amino acid

  摘要：

  For the chemical conversions of a beta-trifluoromethyl-beta-amino acid ((S)-4,4,4-trifluoro-3-aminobutyric acid, 1), such as the N-terminus protection with benzyloxycarbonyl or tert-butoxycarbonyl group, the C-terminus protection with benzyl or tert-butyl group, and peptide elongation at the both termini, highly practical protocols were established. Through these conversions, the stereochemistry of 1 and/or its condensation counterpart was maintained. Because the protocols developed here are indispensable for the application of 1 in peptide engineering, they would expand the utility of 1 and its derivatives. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.051