4-phenyl-3-(2-phenylbutyryl)oxazolidin-2-one

• 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: 4-phenyl-3-(2-phenylbutyryl)oxazolidin-2-one
• 英文别名: (4S)-4-phenyl-3-[(2R)-2-phenylbutanoyl]-1,3-oxazolidin-2-one
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: CFYCBRRWMJHVOV-IAGOWNOFSA-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：
  4
• 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：

  4-phenyl-3-(2-phenylbutyryl)oxazolidin-2-one 、 苏合香醇 在 甲基溴化镁 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 12.17h， 生成 di(1-phenylethyl) carbonate 、 1-phenylethyl 2-phenylbutanoate 、 1-phenylethyl 2-phenylbutanoate 、 (R)-1-phenylethan-1-yl (S)-1-phenylethan-1-yl carbonate
  参考文献：
  名称：

  Probing the parallel kinetic resolution of 1-phenylethanol using quasi-enantiomeric oxazolidinone adducts

  摘要：

  The parallel kinetic resolution of racemic 1-phenylethanol using an equimolar combination of quasi-enantiomeric oxazolidinones is discussed. The levels of diastereoselectivity were high leading to separable quasi-enantiomeric esters in good yield. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.09.015
• 作为产物：
  描述：

  2-苯基丁酸 在 正丁基锂 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 4-phenyl-3-(2-phenylbutyryl)oxazolidin-2-one
  参考文献：
  名称：

  Synthesis, characterisation and application of enantiomeric isotopomers of Evans’ oxazolidinones

  摘要：

  The synthesis of a series of enantiomerically pure deuterium-labelled isotopomeric Evans' oxazolidinones is discussed. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2007.01.003

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.
• Resolution of pentafluorophenyl esters using oxazolidin-2-ones
  作者：Najla Al Shaye、Jason Eames

  DOI：10.1016/j.tetlet.2010.08.109

  日期：2010.11

  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.
• Synthesis, characterisation and application of enantiomeric isotopomers of Evans’ oxazolidinones
  作者：Ewan Boyd、Sameer Chavda、Elliot Coulbeck、Gregory S. Coumbarides、Marco Dingjan、Jason Eames、Anthony Flinn、Aarti K. Krishnamurthy、Mariam Namutebi、Julian Northen、Yonas Yohannes

  DOI：10.1016/j.tetasy.2007.01.003

  日期：2006.12

  The synthesis of a series of enantiomerically pure deuterium-labelled isotopomeric Evans' oxazolidinones is discussed. (c) 2007 Published by Elsevier Ltd.
• Probing the parallel kinetic resolution of 1-phenylethanol using quasi-enantiomeric oxazolidinone adducts
  作者：Elliot Coulbeck、Jason Eames

  DOI：10.1016/j.tetasy.2007.09.015

  日期：2007.9

  The parallel kinetic resolution of racemic 1-phenylethanol using an equimolar combination of quasi-enantiomeric oxazolidinones is discussed. The levels of diastereoselectivity were high leading to separable quasi-enantiomeric esters in good yield. (c) 2007 Elsevier Ltd. All rights reserved.