(S)-五氟苯基2-(4-异丁基苯基)丙酸酯 | 851913-12-7

• 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
• 中文名称: (S)-五氟苯基2-(4-异丁基苯基)丙酸酯
• 英文名称: pentafluorophenyl (S)-2-(4-isobutylphenyl)propionate
• 英文别名: (S)-pentafluorophenyl 2-(4-isobutylphenyl)propionate；(S)-pentafluorophenyl 2-(4-isobutylphenyl)propanoate；(2,3,4,5,6-pentafluorophenyl) (2S)-2-[4-(2-methylpropyl)phenyl]propanoate
• CAS: 851913-12-7
• 化学式: C₁₉H₁₇F₅O₂
• 分子量: 372.335
• InChiKey: OQNMJKIVGHECKH-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  (S)-五氟苯基2-(4-异丁基苯基)丙酸酯 、 (S)-4-异丙基-2-唑烷酮 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以64%的产率得到(4S)-3-<(s'S)-2'-(4-isobutylphenyl)propanoyl>-4-(1-methylethyl)-2-oxazolidinone
  参考文献：
  名称：

  On the structure and chiroptical properties of (S)-4-isopropyl-oxazolidin-2-one

  摘要：

  The specific rotation of (S)-4-isopropyl-oxazolidin-2-one is extremely solvent dependent. In chloroform it is dextrorotatory {[alpha](D)(26) = + 15.5 (c 5.2, CHCl3)}, whereas in ethanol it is levorotatory {[alpha](D)(26) = -16.1 (c 5.2; EtOH)}. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.03.032
• 作为产物：
  描述：

  五氟苯酚 、 (S)-(+)-布洛芬 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92%的产率得到(S)-五氟苯基2-(4-异丁基苯基)丙酸酯
  参考文献：
  名称：

  On the structure and chiroptical properties of (S)-4-isopropyl-oxazolidin-2-one

  摘要：

  The specific rotation of (S)-4-isopropyl-oxazolidin-2-one is extremely solvent dependent. In chloroform it is dextrorotatory {[alpha](D)(26) = + 15.5 (c 5.2, CHCl3)}, whereas in ethanol it is levorotatory {[alpha](D)(26) = -16.1 (c 5.2; EtOH)}. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.03.032

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。
• 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.
• On the structure and chiroptical properties of (S)-4-isopropyl-oxazolidin-2-one
  作者：David Benoit、Elliot Coulbeck、Jason Eames、Majid Motevalli

  DOI：10.1016/j.tetasy.2008.03.032

  日期：2008.5

  The specific rotation of (S)-4-isopropyl-oxazolidin-2-one is extremely solvent dependent. In chloroform it is dextrorotatory [alpha](D)(26) = + 15.5 (c 5.2, CHCl3)}, whereas in ethanol it is levorotatory [alpha](D)(26) = -16.1 (c 5.2; EtOH)}. (C) 2008 Elsevier Ltd. All rights reserved.