(S)-2-phenylbutyric acid anilide | 13490-86-3

• 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)-2-phenylbutyric acid anilide
• 英文别名: (S)-2-phenyl-butyric acid anilide；(S)-2-Phenyl-buttersaeure-anilid；(S)-(+)-α-Aethyl-phenylacetanilid；(2S)-N,2-diphenylbutanamide
• CAS: 13490-86-3
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: BDKOFTGODYDQOQ-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-苯基丁酸 、 苯胺 在 DMT*brucine tetrafluoroborate 、 马钱子碱 作用下， 以 乙腈 为溶剂， 以90%的产率得到(S)-2-phenylbutyric acid anilide
  参考文献：
  名称：

  Design, Synthesis, and Application of Enantioselective Coupling Reagent with a Traceless Chiral Auxiliary

  摘要：

  Stable chiral N-triazinylbrucinium tetrafluoroborate enantioselectively activates racemic carboxylic acids yielding enantiomerically enriched amides, esters, and dipeptides with er from 8:92 to 0.5:99.5. Due to the departure of a chiral auxiliary after the activation of the carboxylic function, all of the subsequent stages of the coupling reaction proceed without any perturbation caused by a chirality discriminator (traceless). Therefore, the advantageous coupling conditions, configuration, and enantiomeric purity of the final product are entirely predictable from the model experiment.

  DOI：

  10.1021/ol802691x

文献信息

• Enantioselective Synthesis of Chiral Amides by a Phosphoric Acid Catalyzed Asymmetric Wolff Rearrangement**
  作者：Jia‐Bin Pan、Zhi‐Chun Yang、Xuan‐Ge Zhang、Mao‐Lin Li、Qi‐Lin Zhou

  DOI：10.1002/anie.202308122

  日期：2023.9.25

  The highly enantioselective synthesis of chiral amides was achieved by an asymmetric Wolff rearrangement. A bifunctional phosphoric acid catalyst not only expedited the transformation but also controlled the enantioselectivity. The developed method enables the asymmetric addition between potent nucleophilic reagents and ketene species and provides a new approach to chiral amides.

  通过不对称沃尔夫重排实现了手性酰胺的高度对映选择性合成。双功能磷酸催化剂不仅能加速转化，还能控制对映选择性。所开发的方法能够实现强效亲核试剂和乙烯酮物种之间的不对称加成，并提供了一种制备手性酰胺的新方法。
• Delepine; Badoche, Annales de Chimie (Cachan, France), 1942, vol. <11> 17, p. 179,180
  作者：Delepine、Badoche

  DOI：——

  日期：——
• The method of preparation of enantiomerically enriched products of condensation from racemic acids or acids of the low enentiomeric purity
  申请人：Politechnika Lódzka

  公开号：EP2418190B1

  公开（公告）日：2013-08-28
• PYRROLOPYRIDAZINE JAK3 INHIBITORS AND THEIR USE FOR THE TREATMENT OF INFLAMMATORY AND AUTOIMMUNE DISEASES
  申请人：Bristol-Myers Squibb Company

  公开号：EP2685982B1

  公开（公告）日：2017-07-05
• Design, Synthesis, and Application of Enantioselective Coupling Reagent with a Traceless Chiral Auxiliary
  作者：Beata Kolesinska、Zbigniew J. Kaminski

  DOI：10.1021/ol802691x

  日期：2009.2.5

  Stable chiral N-triazinylbrucinium tetrafluoroborate enantioselectively activates racemic carboxylic acids yielding enantiomerically enriched amides, esters, and dipeptides with er from 8:92 to 0.5:99.5. Due to the departure of a chiral auxiliary after the activation of the carboxylic function, all of the subsequent stages of the coupling reaction proceed without any perturbation caused by a chirality discriminator (traceless). Therefore, the advantageous coupling conditions, configuration, and enantiomeric purity of the final product are entirely predictable from the model experiment.