2S-(o-phenylbenzoyl)amino-3R-hydroxybutylic acid | 438620-44-1

• 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: 2S-(o-phenylbenzoyl)amino-3R-hydroxybutylic acid
• CAS: 438620-44-1
• 化学式: C₁₇H₁₇NO₄
• 分子量: 299.326
• InChiKey: PYQNLLDGJXUGJP-ABAIWWIYSA-N

物化性质

• 沸点：
  571.4±50.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  86.63
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2S-(o-phenylbenzoyl)amino-3R-hydroxybutylic acid 在 对甲苯磺酸 potassium carbonate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 3-(o-phenylbenzoyl)-2,2,5R-trimethyloxazolidine-4S-carboxylic acid methyl ester
  参考文献：
  名称：

  Highly Enhanced Enantioselectivity in the Memory of Chirality via Acyliminium Ions

  摘要：

  [reaction: see text] Electrochemical oxidation of N-acylated serine derivative 1b in methanol gave optically active methoxylated compound 2b with an enantiomeric excess of up to 80%. The bulky o-phenyl benzoyl N-protecting group was found to be the main contributing factor for the enhanced enantioselectivity. The mechanistic aspect of this methoxylation reaction was investigated and found to proceed via a retention mechanism.

  DOI：

  10.1021/ol025865r
• 作为产物：
  描述：

  L-苏氨酸 、 2-苯基苯甲酰氯 在 sodium hydroxide 作用下， 以95%的产率得到2S-(o-phenylbenzoyl)amino-3R-hydroxybutylic acid
  参考文献：
  名称：

  Highly Enhanced Enantioselectivity in the Memory of Chirality via Acyliminium Ions

  摘要：

  [reaction: see text] Electrochemical oxidation of N-acylated serine derivative 1b in methanol gave optically active methoxylated compound 2b with an enantiomeric excess of up to 80%. The bulky o-phenyl benzoyl N-protecting group was found to be the main contributing factor for the enhanced enantioselectivity. The mechanistic aspect of this methoxylation reaction was investigated and found to proceed via a retention mechanism.

  DOI：

  10.1021/ol025865r