2S-(o-phenylbenzoyl)amino-3S-hydroxybutylic acid methyl ester | 438620-50-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2S-(o-phenylbenzoyl)amino-3S-hydroxybutylic acid methyl ester
• CAS: 438620-50-9
• 化学式: C₁₈H₁₉NO₄
• 分子量: 313.353
• InChiKey: GTXLNYYCTSGEPO-LRDDRELGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  75.63
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2S-(o-phenylbenzoyl)amino-3S-hydroxybutylic acid methyl ester 在 对甲苯磺酸 sodium hydroxide 作用下， 以 四氢呋喃 、 氯仿 、 苯 为溶剂， 反应 24.0h， 生成 3-(o-phenylbenzoyl)-2,2,5S-trimethyloxazolidine-4S-carboxylic 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
• 作为产物：
  描述：

  2-苯基苯甲酰氯 在 sodium hydroxide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2S-(o-phenylbenzoyl)amino-3S-hydroxybutylic 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