(4R,2'R)-3-(2'-phenylpropionyl)-4-phenyl-oxazolidin-2-one | 198344-48-8

• 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: (4R,2'R)-3-(2'-phenylpropionyl)-4-phenyl-oxazolidin-2-one
• 英文别名: (4R)-4-phenyl-3-[(2R)-2-phenylpropionyl]oxazolidin-2-one；(4R,2'R)-4-phenyl-3-(2'-phenylpropionyl)oxazolidin-2-one；(4R)-4-phenyl-3-((2R)-phenylpropanoyl)oxazolidin-2-one；(R)-4-phenyl-3-((R)-2-phenylpropanoyl)oxazolidin-2-one；(4R)-4-phenyl-3-[(2R)-2-phenylpropanoyl]-1,3-oxazolidin-2-one
• CAS: 198344-48-8
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: KSSAAGMVSMKTSX-CJNGLKHVSA-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：

  (4R,2'R)-3-(2'-phenylpropionyl)-4-phenyl-oxazolidin-2-one 在 sodium tetrahydroborate 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以95%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 、 lithium hydroxide monohydrate 、 双氧水 、 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 、 水 为溶剂， 反应 30.25h， 生成 (4R,2'R)-3-(2'-phenylpropionyl)-4-phenyl-oxazolidin-2-one
  参考文献：
  名称：

  Resolution of pentafluorophenyl 2-phenylpropanoate using combinations of quasi-enantiomeric oxazolidin-2-ones

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2011.02.022

文献信息

• Ni-Catalyzed chemoselective alcoholysis of <i>N</i>-acyloxazolidinones
  作者：Pei-Qiang Huang、Hui Geng

  DOI：10.1039/c7gc03534a

  日期：——

  (catalytic) asymmetric synthetic methodologies occupy an important position in modern organic synthesis, the catalytic cleavage of a chiral auxiliary remains underdeveloped. We report the Ni(cod)2/bipyr.-catalyzed alcoholysis of N-acyloxazolidinones to deliver esters. The reaction is broad in scope for both N-acyloxazolidinone substrates and alcohol nucleophiles, and displays good functional group tolerance

  尽管基于N-酰基氧杂唑烷酮的（催化）不对称合成方法在现代有机合成中占有重要地位，但手性助剂的催化裂解仍未开发。我们报告了N（酰基）xx恶唑烷酮的Ni（cod）2 /联吡啶催化的醇解反应以递送酯。该反应对于N-酰基氧杂唑烷酮底物和醇亲核试剂都具有广泛的范围，并且显示出良好的官能团耐受性和优异的化学选择性。克级的甲醇分解作用可以使强效免疫抑制剂FK506的紧密类似物的C22–C26片段进行对映选择性合成。
• 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。
• 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.
• Investigations into the parallel kinetic resolution of 2-phenylpropanoyl chloride using quasi-enantiomeric oxazolidinones
  作者：Sameer Chavda、Elliot Coulbeck、Gregory S. Coumbarides、Marco Dingjan、Jason Eames、Stephanos Ghilagaber、Yonas Yohannes

  DOI：10.1016/j.tetasy.2007.01.002

  日期：2006.12

  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.