(4R)-3-((2S)-2-苯基丙酰基)-4-苯基恶唑烷-2-酮 | 214492-02-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (4R)-3-((2S)-2-苯基丙酰基)-4-苯基恶唑烷-2-酮
• 英文名称: (4R,2'S)-3-(2'-phenylpropionyl)-4-phenyl-oxazolidin-2-one
• 英文别名: (4R,2'S)-4-phenyl-3-(2'-phenylpropionyl)oxazolidin-2-one；(4R)-4-phenyl-3-[(2S)-2-phenylpropionyl]oxazolidin-2-one；(4R)-3-((2S)-2-phenylpropionyl)-4-phenyl-oxazolidin-2-one；(R)-4-phenyl-3-((S)-2-phenylpropanoyl)oxazolidin-2-one；(2'S,4R)-3-(2-phenylpropionyl)-4-phenyloxazolidin-2-one；(4R)-4-phenyl-3-((2S)-phenylpropanoyl)oxazolidin-2-one；(4R)-4-phenyl-3-[(2S)-2-phenylpropanoyl]-1,3-oxazolidin-2-one
• CAS: 214492-02-1
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: KSSAAGMVSMKTSX-BBRMVZONSA-N

物化性质

• 熔点：
  140-142 °C
• 沸点：
  483.8±44.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

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：

  (4R)-3-((2S)-2-苯基丙酰基)-4-苯基恶唑烷-2-酮 在 lithium hydroxide monohydrate 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 以91%的产率得到S-2-苯基丙酸
  参考文献：
  名称：

  Parallel kinetic resolution of active esters using a quasi-enantiomeric combination of (R)-4-phenyl-oxazolidin-2-one and (S)-4,5,5-triphenyl-oxazolidin-2-one

  摘要：

  The parallel kinetic resolution of a series of racemic pentafluorophenyl 2-(4-aryl/phenyl)-propionates and -butanoates using a quasi-enantiomeric combination of (R)-4-phenyl-oxazolidin-2-one and (S)-4,5,5-triphenyl-oxazolidin-2-one is discussed. The levels of diastereoselectivity were excellent (86-98% de) leading to separable quasi-enantiomeric oxazolidin-2-one adducts in good yield. This methodology was used to resolve 2-phenyl propionic acid. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.09.012
• 作为产物：
  描述：

  (4R)-3-((2S)-2-phenylbutanoyl)-4-phenyl-oxazolidin-2-one 在 正丁基锂 、 lithium hydroxide monohydrate 、 双氧水 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 15.0h， 生成 (4R)-3-((2S)-2-苯基丙酰基)-4-苯基恶唑烷-2-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

文献信息

• Direct Lewis Acid Catalyzed Conversion of Enantioenriched <i>N</i>-Acyloxazolidinones to Chiral Esters, Amides, and Acids
  作者：Jason M. Stevens、Ana Cristina Parra-Rivera、Darryl D. Dixon、Gregory L. Beutner、Albert J. DelMonte、Doug E. Frantz、Jacob M. Janey、James Paulson、Michael R. Talley

  DOI：10.1021/acs.joc.8b02451

  日期：2018.12.7

  enabled a unified protocol for the direct conversion of enantioenriched N-acyloxazolidinones to the corresponding chiral esters, amides, and carboxylic acids. This straightforward and catalytic method has shown remarkable chemoselectivity for substitution at the acyclic N-acyl carbonyl for a diverse array of N-acyloxazolidinone substrates. The ionic radius of the Lewis acid catalyst was demonstrated as a

  通过多变量高通量实验策略鉴定Yb（OTf）3，已实现了将富含对映体的N-酰基氧杂唑烷酮直接转化为相应的手性酯，酰胺和羧酸的统一方案。这种直接和催化方法已经显示出显着的化学选择性用于在无环取代的N-酰基羰基为得到大量不同的Ñ -acyloxazolidinone基材。路易斯酸催化剂的离子半径被证明是催化剂性能的关键驱动因素，导致使用催化Y（OTf）3鉴定出医药中间体的稳健且可扩展的酯化反应。
• A new, economical, practical and racemization-free method for the reductive removal of 2-oxazolidinones from N-acyloxazolidinones with sodium borohydride
  作者：Mahavir Prashad、Denis Har、Hong-Yong Kim、Oljan Repic

  DOI：10.1016/s0040-4039(98)01521-4

  日期：1998.9

  A new, economical, practical and racemization-free method for the reductive removal of 2-oxazolidinones by a reduction of N-acyloxazolidinones with sodium borohydride in THF and water is described.

  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。
• Parallel kinetic resolution of active esters using designer oxazolidin-2-ones derived from phenylglycine
  作者：Sameer Chavda、Elliot Coulbeck、Marco Dingjan、Jason Eames、Anthony Flinn、Julian Northen

  DOI：10.1016/j.tetasy.2008.06.020

  日期：2008.7

  The parallel kinetic resolution of racemic pentafluorophenyl 2-phenylpropionate using an equimolar combination of quasi-enantiomeric oxazolidin-2-ones is discussed. The levels of diastereoselectivity were excellent (>90% de) leading to separable quasi-enantiomeric oxazolidin-2-one adducts in good yield. This methodology was subsequently used to resolve a series of 2-aryl propionic and butanoic acids

  讨论了使用准对映体恶唑烷-2-酮的等摩尔组合，消旋外消旋五氟苯基2-苯基丙酸酯的动力学动力学。非对映选择性水平极好（> 90％de），从而导致可分离的准对映异构体恶唑烷-2-一加合物具有良好的收率。该方法学随后用于解析一系列2-芳基丙酸和丁酸。
• 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.