(4RS,2'RS)-3-(2'-phenylpropionyl)-4-phenyl-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: (4RS,2'RS)-3-(2'-phenylpropionyl)-4-phenyl-oxazolidin-2-one
• 英文别名: 4-phenyl-3-(2'-phenylpropionyl)oxazolidin-2-one；3-(2-phenylpropionyl)-4-phenyloxazolidin-2-one；(rac)-anti-4-phenyl-3-(2-phenylpropanoyl)oxazolidin-2-one；(4RS)-4-phenyl-3-((2RS)-phenylpropanoyl)oxazolidin-2-one；(4S)-4-phenyl-3-[(2S)-2-phenylpropanoyl]-1,3-oxazolidin-2-one
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: KSSAAGMVSMKTSX-XJKSGUPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  苏合香醇 、 (4RS,2'RS)-3-(2'-phenylpropionyl)-4-phenyl-oxazolidin-2-one 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 、 erythro-Hydratropasaeure-1-phenylethylester 、 2-(RS)-phenylethyl 2-(RS)-phenylpropanoate 、 (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-苯基丙酸 在 正丁基锂 、 氯化亚砜 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.5h， 生成 (4RS,2'RS)-3-(2'-phenylpropionyl)-4-phenyl-oxazolidin-2-one
  参考文献：
  名称：

  Investigations into the parallel kinetic resolution of 2-phenylpropanoyl chloride using quasi-enantiomeric oxazolidinones

  摘要：

  The resolution of 2-phenylpropanoyl chloride using an equimolar combination of quasi-enantiomeric oxazolidinones is discussed. The levels of diastereoselectivity were found to be dependent upon the structural nature of the metallated oxazolidinone, temperature and metal counter-ion. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.01.002

文献信息

• Reaction of Tributyltin Hydride with α,β-Unsaturated N-Acyloxazolidinones
  作者：Ming-Jung Wu、Chia-Lin Fu、Tsai-Hui Duh、Jiann-Yih Yeh

  DOI：10.1055/s-1996-4240

  日期：1996.4

  The treatment of tributyltin hydride with α-substituted propenoyl oxazolidinones in the presence of a catalytic amount of AIBN gave the tributyltin radical addition adduct when the substituent is an alkyl group. However, when the substituent is an aryl group, the reduction adduct was obtained in modest diastereoselectivity. The yield of this reduction process was improved by using Pd(PPh3)4 as a catalyst. The application of this stereoselective hydrogenation reaction to the synthesis of α-alkyl arylacetic acids is described.

  在一定量的 AIBN 催化下，三丁基氢化锡与δ-取代的丙烯酰噁唑烷酮进行处理，当取代基为烷基时，可得到三丁基锡自由基加成加合物。然而，当取代基为芳基时，还原加合物的非对映选择性较低。使用 Pd(PPh3)4 作为催化剂可以提高还原过程的产率。本文介绍了这种立体选择性氢化反应在合成δ-烷基芳基乙酸中的应用。
• Efficient parallel resolution of an active ester of 2-phenylpropionic acid using quasi-enantiomeric Evans’ oxazolidinones
  作者：Gregory S. Coumbarides、Marco Dingjan、Jason Eames、Anthony Flinn、Julian Northen、Yonas Yohannes

  DOI：10.1016/j.tetlet.2005.02.139

  日期：2005.4

  The parallel kinetic resolution of pentafluorophenyl 2-phenylpropionate using an equimolar combination of quasi-enantiomeric oxazolidinones is discussed. The levels of diastereocontrol were excellent leading to separable quasi-enantiomeric syn-oxa-zolidinone adducts in good yield. (c) 2005 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.
• Resolution of pentafluorophenyl 2-phenylpropanoate using combinations of quasi-enantiomeric oxazolidin-2-ones
  作者：Najla Al Shaye、David M. Benoit、Sameer Chavda、Elliot Coulbeck、Marco Dingjan、Jason Eames、Yonas Yohannes

  DOI：10.1016/j.tetasy.2011.02.022

  日期：2011.2

  The kinetic, mutual and parallel resolution of a series of structurally related active esters derived from 2-phenylpropanoic acid using a combination of quasi-enantiomeric oxazolidin-2-ones is discussed. (C) 2011 Elsevier Ltd. All rights reserved.
• 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.