(R)-pentafluorophenyl 2-phenylpropionate | 878194-06-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: (R)-pentafluorophenyl 2-phenylpropionate
• 英文别名: pentafluorophenyl (R)-2-phenylpropionate；pentafluorophenyl 2-phenylpropanoate；(2,3,4,5,6-pentafluorophenyl) (2R)-2-phenylpropanoate
• CAS: 878194-06-0
• 化学式: C₁₅H₉F₅O₂
• 分子量: 316.227
• InChiKey: CCWYJTZYBNWXOH-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R)-pentafluorophenyl 2-phenylpropionate 、 2-噁唑烷酮,4-(1-甲基乙基)- 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以60%的产率得到
  参考文献：
  名称：

  Efficient Parallel Resolution of Racemic Evans’ Oxazolidinones Usingquasi-Enantiomeric Profens

  摘要：

  借助准对映异构体的普罗芬组合，实现了消旋的埃文斯恶唑啉酮的高效拆分。立体控制水平很高，得到了构型可预测的产物。

  DOI：

  10.1055/s-2005-922784
• 作为产物：
  描述：

  (4S,2'R)-4-iso-propyl-3-(2'-phenylpropionyl)oxazolidin-2-one 在 lithium hydroxide monohydrate 、 双氧水 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 24.25h， 生成 (R)-pentafluorophenyl 2-phenylpropionate
  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

• Resolution of Pentafluorophenyl Active Esters Using (S)-4-Phenyloxazolidin-2-thione
  作者：Jason Eames、Najla Al Shaye、Tom Broughton、Elliot Coulbeck

  DOI：10.1055/s-0028-1088218

  日期：2009.4

  A series of structurally related racemic pentafluorophenyl active esters were resolved using an equimolar amount of (S)-4-phenyloxazolidin-2-thione. The levels of diastereocontrol were found to be excellent (>86% de at ˜30% conversion).

  使用等摩尔量的(S)-4-苯基恶唑啉-2-硫酮解析了一系列结构相关的外消旋五氟苯基活性酯。结果表明，非对映控制水平非常出色（转化率 Ë30%时de>86%）。
• Desymmetrisation of (4R,5S)-4,5-diphenylimidazolidine-2-thione using pentafluorophenyl active esters
  作者：Anna Andreou、Jason Eames、Majid Motevalli、Timothy J. Prior、Michael Watkinson

  DOI：10.1016/j.tetlet.2010.01.019

  日期：2010.3

  (4R,5S)-4,5-Diphenylimidazolidine-2-thione is efficiently desymmetrised by stereorandom deprotonation with NaHMDS, followed by kinetic resolution of the resulting racemic intermediate with an enantiomerically pure pentafluorophenyl active ester. The levels of diastereocontrol were found to be excellent (86-92% de at similar to 30% conversion). This desymmetrisation reaction is an example of a masked resolution. (C) 2010 Elsevier Ltd. All rights reserved.

  (4R,5S)-4,5-二苯基亚氨基硫脲在NaHMDS作用下发生无序去质子化反应，随后通过使用对映体纯的五氟苯基活性酯对生成的外消旋中间体进行动力学拆分。实验发现，双相控制水平极为出色（在约30%转化率时，对映体过量率可达86%-92%）。这一不对称反应是“假性拆分”的一个实例。© 2010 Elsevier Ltd. 保留所有权利。
• Resolution of (4RS,5RS)-4,5-diphenylimidazolidine-2-thione using pentafluorophenyl active esters
  作者：Anna Andreou、Najla Al Shaye、Hannah Brown、Jason Eames

  DOI：10.1016/j.tetlet.2010.10.157

  日期：2010.12

  (4RS,5RS)-4,5-Diphenylimidazolidine-2-thione is resolved efficiently by treatment with NaHMDS and an enantiomerically pure pentafluorophenyl active ester. The levels of diastereocontrol were excellent (up to 90% de). (C) 2010 Elsevier Ltd. All rights reserved.

  (4RS,5RS)-4,5-二苯基咪达灵-2-硫酮在经过NaHMDS和光学纯的五氟苯基活性酯处理后，得以高效拆分。对映异构控制的水平非常出色（高达90% de）。版权© 2010爱思唯尔有限公司，版权所有。
• 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.
• Parallel kinetic resolution of active esters using a quasi-enantiomeric combination of (R)-4-phenyl-oxazolidin-2-one and (S)-4,5,5-triphenyl-oxazolidin-2-one
  作者：Elliot Coulbeck、Jason Eames

  DOI：10.1016/j.tetasy.2008.09.012

  日期：2008.10

  The parallel kinetic resolution of a series of racemic pentafluorophenyl 2-(4-aryl/phenyl)-propionates and -butanoates using a quasi-enantiomeric combination of (R)-4-phenyl-oxazolidin-2-one and (S)-4,5,5-triphenyl-oxazolidin-2-one is discussed. The levels of diastereoselectivity were excellent (86-98% de) leading to separable quasi-enantiomeric oxazolidin-2-one adducts in good yield. This methodology was used to resolve 2-phenyl propionic acid. (C) 2008 Elsevier Ltd. All rights reserved.