(4S,2'R)-4-iso-propyl-3-(2'-phenylpropionyl)oxazolidin-2-one | 311310-18-6

• 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'R)-4-iso-propyl-3-(2'-phenylpropionyl)oxazolidin-2-one
• 英文别名: (4S)-4-isopropyl-3-[(2R)-2-phenylpropionyl]oxazolidin-2-one；(4S,2'R)-4-isopropyl-3-(2'-phenylpropanoyl)oxazolidin-2-one；(4S)-isopropyl-3-((2R)-phenylpropionyl)oxazolidin-2-one；(R,S)-4-isopropyl-3-(2-phenylpropanoyl)oxazolidin-2-one；(4S)-3-[(2R)-2-phenylpropanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 311310-18-6
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: SHDHYNUTZHKTPO-DGCLKSJQSA-N

物化性质

• 熔点：
  140-142 °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'R)-4-iso-propyl-3-(2'-phenylpropionyl)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 (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
• 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 (4S,2'R)-4-iso-propyl-3-(2'-phenylpropionyl)oxazolidin-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

• 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。
• 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.
• 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.
• 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.