(2S,3R)-3-Hydroxy-N-(4-methoxy-phenyl)-2-methyl-3-pyridin-2-yl-propionamide

• 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,3R)-3-Hydroxy-N-(4-methoxy-phenyl)-2-methyl-3-pyridin-2-yl-propionamide
• 英文别名: (2S,3R)-3-hydroxy-N-(4-methoxyphenyl)-2-methyl-3-pyridin-2-ylpropanamide
• 化学式: C₁₆H₁₈N₂O₃
• 分子量: 286.331
• InChiKey: IVEOCQGRNMRFEV-XHDPSFHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  71.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (4-Methoxy-phenyl)-[(3R,4R)-3-methyl-4-pyridin-2-yl-oxetan-(2Z)-ylidene]-amine 在 硫酸 作用下， 以 丙酮 为溶剂， 生成 (2S,3R)-3-Hydroxy-N-(4-methoxy-phenyl)-2-methyl-3-pyridin-2-yl-propionamide 、 (2S,3S)-3-Hydroxy-N-(4-methoxy-phenyl)-2-methyl-3-pyridin-2-yl-propionamide
  参考文献：
  名称：

  2-Iminooxetane chemistry. 3. Synthesis of .beta.-hydroxy amides

  摘要：

  Beta-Hydroxy amides were synthesized by hydrolysis of the corresponding 2-iminooxetanes, which were prepared in a very simple step by lanthanide-catalyzed cycloaddition of aldehydes to ketene imines. The stereochemical outcome of the hydrolysis, performed under neutral (DMSO/H2O) or acidic (H2SO4/H2O) conditions, depends on the steric and electronic nature of the substituents, which play a crucial role in the ring-opening mechanism. Experiments done with O-18-labeled water showed that two alternatives are possible: one involving ring opening of the oxetane at the C4-O bond, the other involving ring opening at the C2-O bond.

  DOI：

  10.1021/jo00045a024

文献信息

• 2-Iminooxetane chemistry. 3. Synthesis of .beta.-hydroxy amides
  作者：Gaetano Barbaro、Arturo Battaglia、Patrizia Giorgianni

  DOI：10.1021/jo00045a024

  日期：1992.9

  Beta-Hydroxy amides were synthesized by hydrolysis of the corresponding 2-iminooxetanes, which were prepared in a very simple step by lanthanide-catalyzed cycloaddition of aldehydes to ketene imines. The stereochemical outcome of the hydrolysis, performed under neutral (DMSO/H2O) or acidic (H2SO4/H2O) conditions, depends on the steric and electronic nature of the substituents, which play a crucial role in the ring-opening mechanism. Experiments done with O-18-labeled water showed that two alternatives are possible: one involving ring opening of the oxetane at the C4-O bond, the other involving ring opening at the C2-O bond.