methyl (3S)-4,4,4-trifluoro-3-[[(1R,2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]cyclohexanecarbonyl]amino]butanoate | 1458674-54-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (3S)-4,4,4-trifluoro-3-[[(1R,2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]cyclohexanecarbonyl]amino]butanoate
• CAS: 1458674-54-8
• 化学式: C₁₇H₂₇F₃N₂O₅
• 分子量: 396.407
• InChiKey: HXOODIUBMFACBA-UTUOFQBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl (S)-4,4,4-trifluoro-3-aminobutyrate hydrochloride 、 (1R,2r)-boc-2-氨基环己烷羧酸 在 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以65%的产率得到methyl (3S)-4,4,4-trifluoro-3-[[(1R,2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]cyclohexanecarbonyl]amino]butanoate
  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