(4R,2'S)-3-[2'-(4-methylphenyl)propionyl]-4-phenyl-oxazolidin-2-one

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (4R,2'S)-3-[2'-(4-methylphenyl)propionyl]-4-phenyl-oxazolidin-2-one
• 英文别名: (2'S,4R)-3-[2-(4-methylphenyl)propionyl]-4-phenyloxazolidin-2-one；(4R)-3-[(2S)-2-(4-methylphenyl)propanoyl]-4-phenyl-1,3-oxazolidin-2-one
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: TUDUYGYXUZBTIZ-YOEHRIQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,2'S)-3-[2'-(4-methylphenyl)propionyl]-4-phenyl-oxazolidin-2-one 在 lithium hydroxide monohydrate 、 双氧水 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 以90%的产率得到(R)-4-苯基-2-唑烷酮
  参考文献：
  名称：

  Efficient parallel resolution of pentafluorophenyl active esters using quasi-enantiomeric combinations of oxazolidin-2-ones

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2011.02.021
• 作为产物：
  描述：

  pentafluorophenyl 2-(4-methylphenyl)propanoate 、 (R)-4-苯基-2-唑烷酮 、 (S)-4-异丙基-2-唑烷酮 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以1%的产率得到(S)-4-Isopropyl-3-((S)-2-p-tolyl-propionyl)-oxazolidin-2-one
  参考文献：
  名称：

  Efficient parallel resolution of pentafluorophenyl active esters using quasi-enantiomeric combinations of oxazolidin-2-ones

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2011.02.021

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.