2-Phenyl-butyric acid 1-phenyl-ethyl ester | 53483-44-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Phenyl-butyric acid 1-phenyl-ethyl ester
• 英文别名: (R)-2-phenylbutyric acid-(R)-1-phenylethyl ester；1-phenylethyl 2-phenylbutyrate
• CAS: 53483-44-6；53483-45-7；84713-91-7
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: VZMJOYOCNMQMOZ-FBMWCMRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  苏合香醇 、 (+/-)-2-phenylbutyric acid vinyl ester 在 lipase B from Candida antatctica 作用下， 以 甲苯 为溶剂， 反应 35.0h， 生成 2-Phenyl-butyric acid 1-phenyl-ethyl ester 、 2-Phenyl-butyric acid 1-phenyl-ethyl ester
  参考文献：
  名称：

  Highly efficient double enantioselection by lipase-catalyzed transesterification of (R,S)-carboxylic acid vinyl esters with (RS)-1-phenylethanol

  摘要：

  Transesterification of the title compounds using lipase B from Candida antarctica in toluene afforded the corresponding esters in good to excellent diastereomeric excess. (R)-2-Phenylpropionic acid-(R)-1-phenethyl ester 4 was isolated in 45% yield and 64% de after 2.5 h, whereas (R)-2-phenylbutyric acid-(R)-1-phenethyl ester 5 was obtained in 40% yield and 56% de after 35 h. A single recrystallization from n-hexane gave 4 with 98% de. In all reactions CAL-B showed excellent enantioselectivity (E > 100) toward (RS)-1-phenylethanol and moderate enantioselectivity (E similar to 10) toward both carboxylic acid vinyl esters. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00073-7

文献信息

• Determining the absolute configuration of hindered secondary alcohols - a modified horeau's method
  作者：David E. Barnekow、John H. Cardellina

  DOI：10.1016/s0040-4039(01)80466-4

  日期：1989.1

  The kinetic resolution of racemic 2-phenylbutyryl chloride by hindered chiral secondary alcohols has been shown to be a viable approach to the determination of the absolute configuration of secondary alcohols through a study of ten chiral alcohols.

  通过研究十种手性醇，受阻手性仲醇对消旋2-苯基丁酰氯的动力学拆分已被证明是确定仲醇绝对构型的可行方法。
• Probing the parallel kinetic resolution of 1-phenylethanol using quasi-enantiomeric oxazolidinone adducts
  作者：Elliot Coulbeck、Jason Eames

  DOI：10.1016/j.tetasy.2007.09.015

  日期：2007.9

  The parallel kinetic resolution of racemic 1-phenylethanol using an equimolar combination of quasi-enantiomeric oxazolidinones is discussed. The levels of diastereoselectivity were high leading to separable quasi-enantiomeric esters in good yield. (c) 2007 Elsevier Ltd. All rights reserved.
• Parallel kinetic resolution of racemic 1-phenylethanol using quasi-enantiomeric combinations of carboxylic acids mediated by N,N′-dicyclohexylcarbodiimide and 3,5-lutidine
  作者：Najla Al Shaye、Andrew N. Boa、Elliot Coulbeck、Jason Eames

  DOI：10.1016/j.tetlet.2008.05.036

  日期：2008.7

  The parallel kinetic resolution of racemic 1-phenylethanol using an equimolar combination of quasienantiomeric 2-arylpropionic and butanoic acids mediated by a N,N'-dicyclohexylcarbodiimide (DCC)/3,5-lutidine coupling is discussed. The levels of diastereoselectivity were high leading to separable quasi-enantiomeric esters in good yield. (C) 2008 Elsevier Ltd. All rights reserved.