(3S)-4,4,4-trifluoro-3-[[(2S)-3-methyl-1-oxo-1-(phenylmethoxyamino)butan-2-yl]amino]butanoic acid | 347383-76-0

• 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: (3S)-4,4,4-trifluoro-3-[[(2S)-3-methyl-1-oxo-1-(phenylmethoxyamino)butan-2-yl]amino]butanoic acid
• CAS: 347383-76-0
• 化学式: C₁₆H₂₁F₃N₂O₄
• 分子量: 362.349
• InChiKey: GHPQFIRLVOSHCR-JSGCOSHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3S)-4,4,4-trifluoro-3-[[(2S)-3-methyl-1-oxo-1-(phenylmethoxyamino)butan-2-yl]amino]butanoic acid 在 palladium dihydroxide 2,4,6-三甲基吡啶 、 N-羟基-7-氮杂苯并三氮唑 、 氢气 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-3-Phenyl-2-[(S)-4,4,4-trifluoro-3-((S)-1-hydroxycarbamoyl-2-methyl-propylamino)-butyrylamino]-propionic acid tert-butyl ester
  参考文献：
  名称：

  10.1002/1099-0690(20022)2002:3<428::aid-ejoc428<3.0.co;2-j

  摘要：

  DOI：

  10.1002/1099-0690(20022)2002:3<428::aid-ejoc428<3.0.co;2-j
• 作为产物：
  描述：

  (S)-2-[(S)-3-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-oxo-1-trifluoromethyl-propylamino]-N-benzyloxy-3-methyl-butyramide 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以60%的产率得到(3S)-4,4,4-trifluoro-3-[[(2S)-3-methyl-1-oxo-1-(phenylmethoxyamino)butan-2-yl]amino]butanoic acid
  参考文献：
  名称：

  10.1002/1099-0690(20022)2002:3<428::aid-ejoc428<3.0.co;2-j

  摘要：

  DOI：

  10.1002/1099-0690(20022)2002:3<428::aid-ejoc428<3.0.co;2-j

文献信息

• Solution/solid-phase synthesis of partially modified retro- ψ [NHCH(CF 3 )]-peptidyl hydroxamates
  作者：Alessandro Volonterio、Pierfrancesco Bravo、Matteo Zanda

  DOI：10.1016/s0040-4039(01)00375-6

  日期：2001.4

  The synthesis of a novel family of partially-modified (PM) retropeptidyl hydroxamates incorporating a [CH(CF3)CH2CO] unit as a surrogate of the conventional malonyl group, has been accomplished both in solution and in solid-phase. The key step is the Michael-type N-addition of free or polymer bound alpha -amino hydroxamates to 3-(E-enoyl)-1,3-oxazolidin-2-ones, which takes place very effectively, although with low stereocontrol. A number of tri- and tetra-peptidyl hydroxamates were obtained either in diastereomerically pure form (by solution-phase synthesist after chromatographic purification), or as mixtures of two epimers in very good chemical purity (by solid-phase, after release from the resin), demonstrating that this method is suitable for preparing combinatorial libraries of PM retro-psi [NHCH(CF3)]-peptidyl hydroxamates for screening as metalloprotease inhibitors. (C) 2001 Elsevier Science Ltd. All rights reserved.