pentafluorophenyl 2-(4-methylphenyl)propanoate | 931405-92-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: pentafluorophenyl 2-(4-methylphenyl)propanoate
• 英文别名: pentafluorophenyl 2-(4-methylphenyl)propionate；(+/-)-pentafluorophenyl 2-p-tolylpropionate
• CAS: 931405-92-4
• 化学式: C₁₆H₁₁F₅O₂
• 分子量: 330.254
• InChiKey: XMEVFHSVTJOBMW-UHFFFAOYSA-N

物化性质

• 熔点：
  37-40 °C
• 沸点：
  360.5±42.0 °C(Predicted)
• 密度：
  1.362±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 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：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  pentafluorophenyl 2-(4-methylphenyl)propanoate 、 苏合香醇 在 叔丁基锂 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 以61%的产率得到2-p-Tolyl-propionic acid 1-phenyl-ethyl ester
  参考文献：
  名称：

  Parallel Kinetic Resolution of 1-Phenylethanol Using Quasi-Enantiomeric Active Esters

  摘要：

  本研究讨论了使用等摩尔组合的准对映五氟苯基酯并行动力学解析外消旋 1-苯基乙醇的过程。非对映选择性水平极高（>88% de），从而以良好的产率获得了可分离的准对映异构酯。

  DOI：

  10.1055/s-2008-1032068
• 作为产物：
  描述：

  五氟苯酚 、 2-(4-甲基苯基)丙酸 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65%的产率得到pentafluorophenyl 2-(4-methylphenyl)propanoate
  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 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.