pentafluorophenyl 2-phenyl-3-methylbutanoate | 1093959-80-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: pentafluorophenyl 2-phenyl-3-methylbutanoate
• CAS: 1093959-80-8
• 化学式: C₁₇H₁₃F₅O₂
• 分子量: 344.281
• InChiKey: XDXCQGBRQOFEFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  (4R,5S)-(+)-4-甲基-5-苯基-2-恶唑啉酮 、 pentafluorophenyl 2-phenyl-3-methylbutanoate 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以15%的产率得到(rac)-anti,syn-4-methyl-5-phenyl-3-[2-phenyl-3-methylbutanoyl]oxazolidin-2-one
  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：

  五氟苯酚 、 2-异丙基-2-苯基乙酸 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 13.08h， 以74%的产率得到pentafluorophenyl 2-phenyl-3-methylbutanoate
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2008.09.012

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%）。