(S)-N,N-Dibenzyl-2-hydroxy-propionamide

• 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: (S)-N,N-Dibenzyl-2-hydroxy-propionamide
• 英文别名: (2S)-N,N-dibenzyl-2-hydroxypropanamide
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: PAMSRCLHRPCYAF-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  布洛芬 、 (S)-N,N-Dibenzyl-2-hydroxy-propionamide 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 (R)-2-(4-Isobutyl-phenyl)-propionic acid (S)-1-dibenzylcarbamoyl-ethyl ester 、 (S)-2-(4-Isobutyl-phenyl)-propionic acid (S)-1-dibenzylcarbamoyl-ethyl ester
  参考文献：
  名称：

  Asymmetric synthesis of (S)-ibuprofen by esterification with amides of (S)-lactic acid as chiral auxiliaries: experimental and theoretical results

  摘要：

  A novel synthesis of chiral ibuprofen by a dynamic kinetic resolution process is described. The racemic ibuprofen was converted into the corresponding diastereomeric mixtures of esters with amides of (S)-lactic acid as chiral auxiliaries, using dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP) as condensation agents. The reactions afforded predominantly one of the two diastereomers with good diastereomeric ratios. The reasons of the stereoselectivity were also investigated by molecular mechanic calculations, using MM2 force fields. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00792-x

文献信息

• Asymmetric synthesis of (S)-ibuprofen by esterification with amides of (S)-lactic acid as chiral auxiliaries: experimental and theoretical results
  作者：Alessandra Ammazzalorso、Rosa Amoroso、Giancarlo Bettoni、Barbara De Filippis、Letizia Giampietro、Marco Pierini、Maria Luisa Tricca

  DOI：10.1016/s0040-4039(02)00792-x

  日期：2002.6

  A novel synthesis of chiral ibuprofen by a dynamic kinetic resolution process is described. The racemic ibuprofen was converted into the corresponding diastereomeric mixtures of esters with amides of (S)-lactic acid as chiral auxiliaries, using dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP) as condensation agents. The reactions afforded predominantly one of the two diastereomers with good diastereomeric ratios. The reasons of the stereoselectivity were also investigated by molecular mechanic calculations, using MM2 force fields. (C) 2002 Elsevier Science Ltd. All rights reserved.