Acetic acid (S)-3-oxo-2-phenyl-isoxazolidin-5-ylmethyl ester | 140384-91-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: Acetic acid (S)-3-oxo-2-phenyl-isoxazolidin-5-ylmethyl ester
• 英文别名: [(5S)-3-oxo-2-phenyl-1,2-oxazolidin-5-yl]methyl acetate
• CAS: 140384-91-4
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: TUFOLDZOHNDHTA-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.29
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• 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

• 作为产物：
  描述：

  (+/-)-2-phenyl-5-(hydroxymethyl)isoxazolidin-3-one acetate 在 carboxylesterase NP potassium phosphate buffer 作用下， 以 丙酮 为溶剂， 反应 1.08h， 生成 (5S)-5-(hydroxymethyl)-2-phenyl-1,2-oxazolidin-3-one 、 3-异噁唑烷酮,5-(羟甲基)-2-苯基-,(R)- 、 Acetic acid (S)-3-oxo-2-phenyl-isoxazolidin-5-ylmethyl ester
  参考文献：
  名称：

  Nitrile oxides in medicinal chemistry. 4. Chemoenzymic synthesis of chiral heterocyclic derivatives

  摘要：

  The two enantiomers of 3-bromo-5-(hydroxymethyl)-DELTA-2-isoxazoline (1) and 2-phenyl-5-(hydroxymethyl)-isoxazolidin-3-one (9) have been prepared in enantiomeric excess higher than 90% by hydrolysis of the corresponding butyrates under the catalysis of lipase PS, which was the most selective catalyst of the enzymes tested. The pairs of enantiomers of 1 and 9 were transformed into the chiral forms of the potent muscarinic ligands 3 and 5. The results obtained with the homogeneous set of esters 6, 7, 10a-d evidence a strong dependence of reaction rate and enantioselectivity of the lipase PS-catalyzed transformations upon both the size of the acyl moiety and the shape of the group carrying the alcoholic part of the ester. In the series of esters 10a-d, the best results were obtained with butyrate 10b. Quite interestingly, on passing from the butyrate of 1 to that of 9, the value of the enantiomeric ratio remained remarkably high but the enantiopreference switched from R to S. In between lies the butyrate of 2-methyl-5-(hydroxymethyl)isoxazolidin-3-one [(+/-)-6] which was barely recognized by lipase PS and yielded alcohol (R)-(-)-2 in a modest enantiomeric excess.

  DOI：

  10.1021/jo00036a013

文献信息

• Nitrile oxides in medicinal chemistry. 4. Chemoenzymic synthesis of chiral heterocyclic derivatives
  作者：Marco De Amici、Paolo Magri、Carlo De Micheli、Francesca Cateni、Roberto Bovara、Giacomo Carrea、Sergio Riva、Gianluigi Casalone

  DOI：10.1021/jo00036a013

  日期：1992.5

  The two enantiomers of 3-bromo-5-(hydroxymethyl)-DELTA-2-isoxazoline (1) and 2-phenyl-5-(hydroxymethyl)-isoxazolidin-3-one (9) have been prepared in enantiomeric excess higher than 90% by hydrolysis of the corresponding butyrates under the catalysis of lipase PS, which was the most selective catalyst of the enzymes tested. The pairs of enantiomers of 1 and 9 were transformed into the chiral forms of the potent muscarinic ligands 3 and 5. The results obtained with the homogeneous set of esters 6, 7, 10a-d evidence a strong dependence of reaction rate and enantioselectivity of the lipase PS-catalyzed transformations upon both the size of the acyl moiety and the shape of the group carrying the alcoholic part of the ester. In the series of esters 10a-d, the best results were obtained with butyrate 10b. Quite interestingly, on passing from the butyrate of 1 to that of 9, the value of the enantiomeric ratio remained remarkably high but the enantiopreference switched from R to S. In between lies the butyrate of 2-methyl-5-(hydroxymethyl)isoxazolidin-3-one [(+/-)-6] which was barely recognized by lipase PS and yielded alcohol (R)-(-)-2 in a modest enantiomeric excess.