3-(o-phenylbenzoyl)-2,2,5S-trimethyloxazolidine-4S-carboxylic acid methyl ester | 438620-52-1

• 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: 3-(o-phenylbenzoyl)-2,2,5S-trimethyloxazolidine-4S-carboxylic acid methyl ester
• CAS: 438620-52-1
• 化学式: C₂₁H₂₃NO₄
• 分子量: 353.418
• InChiKey: DHWRLBPYMHYAMK-KSSFIOAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(o-phenylbenzoyl)-2,2,5S-trimethyloxazolidine-4S-carboxylic acid methyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以80%的产率得到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：

  2S-(o-phenylbenzoyl)amino-3S-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)-2,2,5S-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