(S)-4-(1-((tert-butoxycarbonyl)amino)-2-(methylamino)-2-oxoethyl)benzoic acid | 944910-70-7

• 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: (S)-4-(1-((tert-butoxycarbonyl)amino)-2-(methylamino)-2-oxoethyl)benzoic acid
• CAS: 944910-70-7
• 化学式: C₁₅H₂₀N₂O₅
• 分子量: 308.334
• InChiKey: VNGFMSSSGOMGPH-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  104.73
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-4-(1-((tert-butoxycarbonyl)amino)-2-(methylamino)-2-oxoethyl)benzoic acid 、 (2-氨基-4-(噻吩-2-基)苯基)氨基甲酸叔丁酯 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Phenylglycine and phenylalanine derivatives as potent and selective HDAC1 inhibitors (SHI-1)

  摘要：

  An HTS screening campaign identified a series of low molecular weight phenols that showed excellent selectivity (> 100-fold) for HDAC1/HDAC2 over other Class I and Class II HDACs. Evolution and optimization of this HTS hit series provided HDAC1-selective (SHI-1) compounds with excellent anti-proliferative activity and improved physical properties. Dose-dependent efficacy in a mouse HCT116 xenograft model was demonstrated with a phenylglycine SHI-1 analog. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.02.012
• 作为产物：
  描述：

  、 一氧化碳 在 palladium diacetate 、 1,3-双(二苯基膦)丙烷 、 N,N-二异丙基乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以95%的产率得到(S)-4-(1-((tert-butoxycarbonyl)amino)-2-(methylamino)-2-oxoethyl)benzoic acid
  参考文献：
  名称：

  Suppression of racemization in the carbonylation of amino acid-derived aryl triflates

  摘要：

  The carbonylation of enantiopure phenylglycine-derived aryl triflates was achieved to afford 4-carboxyphenylglycine analogs with high enantiomeric excesses (88 to >99% ee). Amide analogs of phenylglycine were well-tolerated in the hydroxy- and methoxycarbonylation processes, providing efficient access to benzoic acid and ester building blocks. The % ee of the product was dependent on the relative steric bulk of both the amino acid substrate and the requisite amine base, with (Pr2NEt)-Pr-i proving optimal in minimizing product racemization. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.04.145