(4S,2'S)-4-isopropyl-3-(2'-phenylpropanoyl)oxazolidin-2-one | 311310-15-3

• 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,2'S)-4-isopropyl-3-(2'-phenylpropanoyl)oxazolidin-2-one
• 英文别名: (4S)-isopropyl-3-((2S)-phenylpropionyl)oxazolidin-2-one；(4S,2'S)-4-iso-propyl-3-(2'-phenylpropionyl)oxazolidin-2-one；(4S)-4-isopropyl-3-[(2S)-2-phenylpropionyl]oxazolidin-2-one；(S)-4-isopropyl-3-((S)-2-phenylpropanoyl)oxazolidin-2-one；(S,S)-4-isopropyl-3-(2-phenylpropanoyl)oxazolidin-2-one；(4S)-3-[(2S)-2-phenylpropanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 311310-15-3
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: SHDHYNUTZHKTPO-WCQYABFASA-N

物化性质

• 熔点：
  158-160 °C
• 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,2'S)-4-isopropyl-3-(2'-phenylpropanoyl)oxazolidin-2-one 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 以99%的产率得到S-2-苯基丙酸
  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
• 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， 反应 15.25h， 生成 (4S,2'S)-4-isopropyl-3-(2'-phenylpropanoyl)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

• SuperQuat 5,5-dimethyl-4-iso-propyloxazolidin-2-one as a mimic of Evans 4-tert-butyloxazolidin-2-one
  作者：Steven D. Bull、Stephen G. Davies、A. Christopher Garner、Dennis Kruchinin、Min-Suk Key、Paul M. Roberts、Edward D. Savory、Andrew D. Smith、James E. Thomson

  DOI：10.1039/b605244d

  日期：——

  The incorporation of a gem-dimethyl group at the 5-position of a chiral oxazolidinone biases the conformation of the adjacent C(4)-stereodirecting group such that the gem-dimethyl-4-iso-propyl combination mimics a C(4)-tert-butyl group, providing higher levels of stereocontrol than a simple 4-iso-propyloxazolidinone. The generality of this principle is demonstrated with applications in stereoselective enolate alkylations, kinetic resolutions, Diels–Alder cycloadditions and Pd-catalysed asymmetric acetalisation reactions.

  在手性噁唑啉酮的5位引入一个双甲基基团会使得邻近的C(4)立体导向基团倾向于特定构象，即双甲基-4-异丙基的组合能模拟一个C(4)叔丁基基团，从而实现更高的立体控制水平，优于简单的4-异丙基噁唑啉酮。这一原理的普遍性在立体选择性烯醇化物烷基化、动力学拆分、狄尔斯-阿尔德环加成和钯催化的不对称缩醛化反应中得到了应用验证。
• 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 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.
• Resolution of pentafluorophenyl esters using oxazolidin-2-ones
  作者：Najla Al Shaye、Jason Eames

  DOI：10.1016/j.tetlet.2010.08.109

  日期：2010.11

  A series of structurally related racemic pentafluorophenyl active esters were resolved using an equimolar amount of (S)-4-phenyloxazolidin-2-one. The levels of diastereocontrol were found to be excellent (80-96% de) at similar to 40% conversion. (C) 2010 Elsevier Ltd. All rights reserved.