(S)-pentafluorophenyl 2-phenylbutanoate | 1169704-45-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: (S)-pentafluorophenyl 2-phenylbutanoate
• 英文别名: pentafluorophenyl 2-phenylbutanoate；(2,3,4,5,6-pentafluorophenyl) (2S)-2-phenylbutanoate
• CAS: 1169704-45-3
• 化学式: C₁₆H₁₁F₅O₂
• 分子量: 330.254
• InChiKey: MMHMPEBAEGHSRQ-VIFPVBQESA-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：

  2-甲基-1-苯基-1-丙醇 、 (S)-pentafluorophenyl 2-phenylbutanoate 在 zinc(II) chloride 、 lithium tert-butoxide 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以40%的产率得到异丁酰苯
  参考文献：
  名称：

  Resolution of secondary arylalkyl alcohols using pentafluorophenyl 2-phenylbutanoate and zinc chloride

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2009.05.046
• 作为产物：
  描述：

  (+/-)-pentafluorophenyl 2-phenylbutyrate 、 (S)-4-苯基-2-恶唑烷酮 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以43%的产率得到4-phenyl-3-(2-phenylbutyryl)oxazolidin-2-one
  参考文献：
  名称：

  Resolution of pentafluorophenyl esters using oxazolidin-2-ones

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2010.08.109

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%）。
• 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。
• 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.