(S)-3-((S)-2-(4-chlorophenyl)propanoyl)-4-phenyloxazolidin-2-one | 1308659-01-9

• 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: (S)-3-((S)-2-(4-chlorophenyl)propanoyl)-4-phenyloxazolidin-2-one
• CAS: 1308659-01-9
• 化学式: C₁₈H₁₆ClNO₃
• 分子量: 329.783
• InChiKey: SHGQUUVQTLIZQI-BLLLJJGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  pentafluorophenyl 2-(4-chlorophenyl)propanoate 、 (S)-4-苯基-2-恶唑烷酮 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 生成 (4S)-3-[(2R)-2-(4-chlorophenyl)propionyl]-4-phenyl-oxazolidin-2-one 、 pentafluorophenyl 2-(4-chlorophenyl)propanoate 、 (S)-3-((S)-2-(4-chlorophenyl)propanoyl)-4-phenyloxazolidin-2-one
  参考文献：
  名称：

  Resolution of pentafluorophenyl esters using oxazolidin-2-ones

  摘要：

  A series of structurally related racemic pentafluorophenyl active esters were resolved using an equimolar amount of (S)-4-phenyloxazolidin-2-one. The levels of diastereocontrol were found to be excellent (80-96% de) at similar to 40% conversion. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.08.109

文献信息

• Efficient parallel resolution of pentafluorophenyl active esters using quasi-enantiomeric combinations of oxazolidin-2-ones
  作者：Najla Al Shaye、Sameer Chavda、Elliot Coulbeck、Jason Eames、Yonas Yohannes

  DOI：10.1016/j.tetasy.2011.02.021

  日期：2011.2

  The parallel resolution of racemic pentafluorophenyl 2-aryl/phenylpropanoates and butanoates using an equimolar combination of quasi-enantiomeric Evans oxazolidin-2-ones is discussed. The levels of diastereoselectivity were excellent (>90% de) leading to separable quasi-enantiomeric oxazolidin-2-ones in good yield. This methodology was used to resolve a series of structurally related 2-aryl/phenylpropanoic and butanoic acids. (C) 2011 Elsevier Ltd. All rights reserved.