(+/-)-(4S)-4-isopropyl-3-[(2S)-2-phenylpropionyl]oxazolidin-2-one | 214492-01-0

• 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: (+/-)-(4S)-4-isopropyl-3-[(2S)-2-phenylpropionyl]oxazolidin-2-one
• 英文别名: (rac)-anti-4-isopropyl-3-(2-phenylpropanoyl)oxazolidin-2-one；4-isopropyl-3-(2-phenylpropionyl)oxazolidin-2-one；(4R)-3-[(2R)-2-phenylpropanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 214492-01-0
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: SHDHYNUTZHKTPO-YPMHNXCESA-N

物化性质

• 沸点：
  406.2±24.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  (+/-)-(4S)-4-isopropyl-3-[(2S)-2-phenylpropionyl]oxazolidin-2-one 在 sodium tetrahydroborate 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以88%的产率得到(R)-(+)-2-苯基-1-丙醇
  参考文献：
  名称：

  一种新型，经济，实用，无消旋的新方法，用于用硼氢化钠从N-酰基恶唑烷酮中还原去除2-恶唑烷酮

  摘要：

  描述了一种新的，经济的，实用的和无消旋的方法，该方法通过在THF和水中用硼氢化钠还原N-酰基恶唑烷酮来还原去除2-恶唑烷酮。

  DOI：

  10.1016/s0040-4039(98)01521-4
• 作为产物：
  描述：

  2-苯基丙酸 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， 生成 (+/-)-(4S)-4-isopropyl-3-[(2S)-2-phenylpropionyl]oxazolidin-2-one
  参考文献：
  名称：

  Efficient parallel resolution of an active ester of 2-phenylpropionic acid using quasi-enantiomeric Evans’ oxazolidinones

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2005.02.139

文献信息

• Conformational control in the SuperQuat chiral auxiliary 5,5-dimethyl-4-iso-propyloxazolidin-2-one induces the iso-propyl group to mimic a tert-butyl group
  作者：Steven D. Bull、Stephen G. Davies、Min-Suk Key、Rebecca L. Nicholson、Edward D. Savory

  DOI：10.1039/b005419o

  日期：——

  1 H NMR nOe spectroscopic studies reveal that conformational control in the enolates of N-acyl-5,5-dimethyl-4-iso-propyloxazolidin-2-ones ensures that the stereodirecting effect of its 4-iso-propyl-5,5-dimethyl functional group affords superior levels of facial selectivity normally associated with enolates derived from N-acyl-4-tert-butyloxazolidin-2-ones.

  1 H NMR nOe 光谱研究表明，N-酰基-5,5-二甲基-4-异丙基恶唑啉-2-酮烯醇盐的构象控制确保了其 4-异丙基-5,5-二甲基官能团的立体定向效应，从而提供了通常与 N-酰基-4-叔丁基恶唑啉-2-酮烯醇盐相关的卓越的面部选择性。
• 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.
• 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.
• Parallel kinetic resolution of racemic oxazolidinones using quasi-enantiomeric active esters
  作者：Ewan Boyd、Elliot Coulbeck、Gregory S. Coumbarides、Sameer Chavda、Marco Dingjan、Jason Eames、Anthony Flinn、Majid Motevalli、Julian Northen、Yonas Yohannes

  DOI：10.1016/j.tetasy.2007.10.009

  日期：2007.10

  Racemic Evans' oxazolidinones were efficiently resolved using a combination of quasi-enantiomeric profens. The levels of stereocontrol were high, leading to products with predictable configurations. (c) 2007 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.