(5S)-5-(hydroxymethyl)-2-phenyl-1,2-oxazolidin-3-one | 140384-89-0

• 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: (5S)-5-(hydroxymethyl)-2-phenyl-1,2-oxazolidin-3-one
• CAS: 140384-89-0
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: MHWJNLXFSBZBHP-VIFPVBQESA-N

物化性质

• 沸点：
  317.0±34.0 °C(Predicted)
• 密度：
  1.287±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5S)-5-(hydroxymethyl)-2-phenyl-1,2-oxazolidin-3-one 以 乙醚 、 丙酮 为溶剂， 生成 (S)-(+)-2-phenyl-5-<(dimethylamino)methyl>isoxazolidin-3-one methiodide
  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
• 作为产物：
  描述：

  (+/-)-2-phenyl-5-(hydroxymethyl)isoxazolidin-3-one 在 Lipase PS 吡啶 、 potassium phosphate buffer 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 (5S)-5-(hydroxymethyl)-2-phenyl-1,2-oxazolidin-3-one
  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. 5. Lipase PS-catalyzed resolution of a set of heterocyclic derivatives.
  作者：Giacomo Carrea、Marco de Amici、Carlo de Micheli、Paola Liverani、Marta Carnielli、Sergio Riva

  DOI：10.1016/s0957-4166(00)80155-x

  日期：1993.5

  Lipase from Pseudomonas cepacia (lipase PS) catalyzed the hydrolysis of a series of butyrates of racemic primary alcohols carrying a Δ2-isoxazoline or an isoxazolidin-3-one nucleus. Within this set of compounds, the enantiopreference of the catalyst can be accounted for by a rule recently proposed for lipase PS-catalyzed resolution of secondary alcohols. Nevertheless much work needs to be done in order

  从脂肪酶洋葱假单胞菌（脂肪酶PS）催化的一系列承载Δ外消旋伯醇丁酸酯的水解2 -isoxazoline或异恶唑烷-3-酮核。在这组化合物中，催化剂的对映体优先性可通过最近提出的关于脂肪酶PS催化仲醇拆分的规则来解释。然而，为了预测对映选择性的程度和相对反应速率，需要做很多工作。
• 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.