(+/-)-pentafluorophenyl 2-phenylbutyrate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: (+/-)-pentafluorophenyl 2-phenylbutyrate
• 英文别名: pentafluorophenyl 2-phenylbutanoate；(2,3,4,5,6-Pentafluorophenyl) 2-phenylbutanoate
• 化学式: C₁₆H₁₁F₅O₂
• 分子量: 330.254
• InChiKey: MMHMPEBAEGHSRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  (+/-)-pentafluorophenyl 2-phenylbutyrate 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (S)-1-((4S,5S)-4,5-diphenyl-2-thioxoimidazolidin-1-yl)-2-phenylbutan-1-one
  参考文献：
  名称：

  Resolution of (4RS,5RS)-4,5-diphenylimidazolidine-2-thione using pentafluorophenyl active esters

  摘要：

  (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。

  DOI：

  10.1016/j.tetlet.2010.10.157
• 作为产物：
  描述：

  五氟苯酚 、 2-苯基丁酸 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以72%的产率得到(+/-)-pentafluorophenyl 2-phenylbutyrate
  参考文献：
  名称：

  Synthesis, characterisation and application of enantiomeric isotopomers of Evans’ oxazolidinones

  摘要：

  The synthesis of a series of enantiomerically pure deuterium-labelled isotopomeric Evans' oxazolidinones is discussed. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2007.01.003

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%）。
• 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.
• 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 secondary arylalkyl alcohols using pentafluorophenyl 2-phenylbutanoate and zinc chloride
  作者：Elliot Coulbeck、Jason Eames

  DOI：10.1016/j.tetlet.2009.05.046

  日期：2009.8

  The resolution of racemic secondary arylalkyl alcohols using pentafluorophenyl 2-phenylbutanoate and zinc chloride is discussed. The levels of enantiomeric recognition were high leading to enantiomerically enriched alcohols in good yield. (C) 2009 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.