(rac)-anti-4-benzyl-3-(2-phenylpropanoyl)oxazolidine-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: (rac)-anti-4-benzyl-3-(2-phenylpropanoyl)oxazolidine-2-one
• 英文别名: (rac)-anti-4-benzyl-3-(2-phenylpropanoyl)oxazolidin-2-one；4-benzyl-3-(2-phenylpropionyl)oxazolidin-2-one；(4S)-4-benzyl-3-[(2S)-2-phenylpropanoyl]-1,3-oxazolidin-2-one
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: BXUPGDHRJVQFMQ-YOEHRIQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 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：

  (rac)-anti-4-benzyl-3-(2-phenylpropanoyl)oxazolidine-2-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以75%的产率得到(S)-2-苯基-1-丙醇
  参考文献：
  名称：

  铁卡宾配合物分子内 C-H 插入反应的立体化学探针

  摘要：

  DOI：

  10.1021/ja000239f
• 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 (rac)-anti-4-benzyl-3-(2-phenylpropanoyl)oxazolidine-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

• 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。
• Catalyst- and solvent-free aminolysis of the asymmetric derivatives of Evans’ chiral <i>N</i>-acyloxazolidinones: enantioselective synthesis of chiral amides and its applications
  作者：Hui-Rong Lu、Hui Geng、Guan-Tian Ding、Pei-Qiang Huang

  DOI：10.1039/d2gc00662f

  日期：——

  areas for the pharmaceutical industry. Here, we report a catalyst- and solvent-free protocol for the aminolysis of the asymmetric derivatives of Evans’ N-acyloxazolidinones to deliver enantioenriched secondary amides. This constitutes an extension of the Evans asymmetric methodology for the enantioselective synthesis of chiral common amides. The reaction features simplicity (without using any catalyst,

  酰胺键的绿色形成被确定为制药行业的关键绿色化学研究领域之一。在这里，我们报告了一种无催化剂和无溶剂方案，用于对 Evans 的N -acyloxazolidinones 的不对称衍生物进行氨解以提供对映体富集的二级酰胺。这构成了 Evans 不对称方法的扩展，用于手性常见酰胺的对映选择性合成。该反应具有简单（不使用任何催化剂、溶剂或添加剂）、温和（在室温下运行）、多功能性（适用于不同类型的N基于-酰基恶唑烷酮的不对称产物和用于α-支链伯胺），以及高效率和选择性（高收率和高ee）。该方法的附加价值通过将酰胺一锅法转化为其他类别的化合物来证明。
• 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.
• 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.