2-methyl-5-(hydroxymethyl)isoxazolidin-3-one | 124498-17-5

• 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: 2-methyl-5-(hydroxymethyl)isoxazolidin-3-one
• 英文别名: 5-(Hydroxymethyl)-2-methyl-1,2-oxazolidin-3-one
• CAS: 124498-17-5
• 化学式: C₅H₉NO₃
• 分子量: 131.131
• InChiKey: SLDGUIZDBMQCBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  2-methyl-5-(hydroxymethyl)isoxazolidin-3-one 在 劳森试剂 、 吡啶 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 1.0h， 生成 2-methyl-5-dimethylaminomethylisoxazolidin-3-thione methiodide
  参考文献：
  名称：

  Synthesis and pharmacological investigation of cholinergic ligands structurally related to muscarone

  摘要：

  DOI：

  10.1016/0223-5234(89)90111-6
• 作为产物：
  描述：

  (+/-)-3-bromo-5-hydroxymethyl isoxazoline 、 trimethoxonium tetrafluoroborate 在 碳酸氢钠 作用下， 生成 2-methyl-5-(hydroxymethyl)isoxazolidin-3-one
  参考文献：
  名称：

  Synthesis and pharmacological investigation of cholinergic ligands structurally related to muscarone

  摘要：

  DOI：

  10.1016/0223-5234(89)90111-6

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.
• DE, AMICI MARCO;DE, MICHELI CARLO;GRANA, ENZO;RODI, ROBERTO;ZONTA, FRANCO+, EUR. J. MED. CHEM., 24,(1989) N, C. 171-177
  作者：DE, AMICI MARCO、DE, MICHELI CARLO、GRANA, ENZO、RODI, ROBERTO、ZONTA, FRANCO+

  DOI：——

  日期：——
• Synthesis and pharmacological investigation of cholinergic ligands structurally related to muscarone
  作者：Marco De Amici、Carlo De Micheli、Enzo Grana、Roberto Rodi、Franco Zonta、Maria Grazia Santagostino-Barbone

  DOI：10.1016/0223-5234(89)90111-6

  日期：1989.3