(4R,2'S)-3-[2'-(6-methoxy-naphthalen-2-yl)propionyl]-4-phenyl-oxazolidin-2-one | 878194-08-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (4R,2'S)-3-[2'-(6-methoxy-naphthalen-2-yl)propionyl]-4-phenyl-oxazolidin-2-one
• 英文别名: (4R)-3-[(2S)-2-(6-methoxynaphth-2-yl)propionyl]-4-phenyloxazolidin-2-one；3-[2-(6-methoxy-naphthalen-2-yl)-propionyl]-4-phenyloxazolidin-2-one；(2'S,4R)-3-[2-(6-methoxynaphthalen-2-yl)propionyl]-4-phenyloxazolidin-2-one；(4R)-3-[(2S)-2-(6-methoxynaphthalen-2-yl)propanoyl]-4-phenyl-1,3-oxazolidin-2-one
• CAS: 878194-08-2
• 化学式: C₂₃H₂₁NO₄
• 分子量: 375.424
• InChiKey: ANQVUQXOPUUSAV-BTYIYWSLSA-N

物化性质

• 熔点：
  168-170 °C
• 沸点：
  592.6±50.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,2'S)-3-[2'-(6-methoxy-naphthalen-2-yl)propionyl]-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
• 作为产物：
  描述：

  (+)-pentafluorophenyl 2-(6-methoxy-naphthalen-2-yl)propionate 、 4-phenyl-2-oxazolidinone 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以53%的产率得到(4R,2'S)-3-[2'-(6-methoxy-naphthalen-2-yl)propionyl]-4-phenyl-oxazolidin-2-one
  参考文献：
  名称：

  Parallel kinetic resolution of racemic oxazolidinones using quasi-enantiomeric active esters

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2007.10.009

文献信息

• Probing the parallel kinetic resolution of 1-phenylethanol using quasi-enantiomeric oxazolidinone adducts
  作者：Elliot Coulbeck、Jason Eames

  DOI：10.1016/j.tetasy.2007.09.015

  日期：2007.9

  The parallel kinetic resolution of racemic 1-phenylethanol using an equimolar combination of quasi-enantiomeric oxazolidinones is discussed. The levels of diastereoselectivity were high leading to separable quasi-enantiomeric esters in good yield. (c) 2007 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.