Ethyl (S)-3-((tert-butoxycarbonyl)amino)-4,4,4-trifluorobutanoate | 1458674-48-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Ethyl (S)-3-((tert-butoxycarbonyl)amino)-4,4,4-trifluorobutanoate
• 英文别名: ethyl (3S)-4,4,4-trifluoro-3-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 1458674-48-0
• 化学式: C₁₁H₁₈F₃NO₄
• 分子量: 285.263
• InChiKey: ZONGJNNSYPZTLQ-ZETCQYMHSA-N

物化性质

• 沸点：
  298.2±40.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Ethyl (S)-3-((tert-butoxycarbonyl)amino)-4,4,4-trifluorobutanoate 在 lithium hydroxide monohydrate 、 水 、 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 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 Boc-bAla(3R-CF3)-Ser(Bn)-OMe
  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)-4,4,4-trifluoro-3-aminobutyrate hydrochloride 、 二碳酸二叔丁酯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以82%的产率得到Ethyl (S)-3-((tert-butoxycarbonyl)amino)-4,4,4-trifluorobutanoate
  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