(R,R)-2-phenylpropionic anhydride | 274905-78-1

• 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: (R,R)-2-phenylpropionic anhydride
• 英文别名: [(2R)-2-phenylpropanoyl] (2R)-2-phenylpropanoate
• CAS: 274905-78-1
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: XXVXJBZRUDZPSL-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2R)-1,2-diphenylethane-1,2-diol 、 (R,R)-2-phenylpropionic anhydride 在 cerium(III) chloride 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-2-Phenyl-propionic acid (1R,2S)-2-hydroxy-1,2-diphenyl-ethyl ester 、 (S)-2-Phenyl-propionic acid (1R,2S)-2-hydroxy-1,2-diphenyl-ethyl ester
  参考文献：
  名称：

  Direct one step mono-functionalisation of symmetrical 1,2-diols

  摘要：

  The mono-functionalisation of meso- and C-2-symmetric diols has been achieved via the use of a new lanthanide(III) chloride catalysed acylation reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00224-0
• 作为产物：
  描述：

  (R)-(-)-2-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， 以83%的产率得到(R,R)-2-phenylpropionic anhydride
  参考文献：
  名称：

  A method for determining the enantiomeric purity of profens

  摘要：

  A simple method for determining the enantiomeric purity of profens (based on the carbon skeleton of 2-phenylpropionic acid) is discussed. The enantiomeric purity of a given profen can be determined by stereospecific DCC self-coupling to give a statistical diastereoisomeric mixture of racemic and meso- anhydrides. The relative ratio of diastereoisomers formed can be related to the enantiomeric excess of the original carboxylic acid. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.051

文献信息

• A method for determining the enantiomeric purity of profens
  作者：Elliot Coulbeck、Jason Eames

  DOI：10.1016/j.tetasy.2009.02.051

  日期：2009.3

  A simple method for determining the enantiomeric purity of profens (based on the carbon skeleton of 2-phenylpropionic acid) is discussed. The enantiomeric purity of a given profen can be determined by stereospecific DCC self-coupling to give a statistical diastereoisomeric mixture of racemic and meso- anhydrides. The relative ratio of diastereoisomers formed can be related to the enantiomeric excess of the original carboxylic acid. (C) 2009 Elsevier Ltd. All rights reserved.
• Direct one step mono-functionalisation of symmetrical 1,2-diols
  作者：Paul A Clarke、Robert A Holton、Nadim E Kayaleh

  DOI：10.1016/s0040-4039(00)00224-0

  日期：2000.4

  The mono-functionalisation of meso- and C-2-symmetric diols has been achieved via the use of a new lanthanide(III) chloride catalysed acylation reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.