(S)-2-tert-butylamino-N-phenylpropanamide | 138891-31-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-tert-butylamino-N-phenylpropanamide
• 英文别名: S-(-)-2-(tert-butylamino)propananilide；(2S)-2-(tert-butylamino)-N-phenylpropanamide
• CAS: 138891-31-3
• 化学式: C₁₃H₂₀N₂O
• 分子量: 220.315
• InChiKey: OWXAKHYUCDWTCF-JTQLQIEISA-N

物化性质

• 沸点：
  365.9±25.0 °C(Predicted)
• 密度：
  1.028±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-2-bromo-N-phenylpropanamide 、 叔丁胺 在 silver(l) oxide 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以86%的产率得到(S)-2-tert-butylamino-N-phenylpropanamide
  参考文献：
  名称：

  2-溴丙酰胺与伯仲或叔胺的对映选择性反应。某些丙氨酰胺的合成。

  摘要：

  在室温下，对映体2-溴丙酰胺与伯，仲或叔脂族胺在甲苯中反应，生成相应的仲或叔氨基或季铵酰胺。如果反应的胺是良好的亲核试剂，则通过在有或没有Ag 2 O的条件下进行反应，均可以高收率和ee的形式获得任何一种产物。在亲核胺较少的情况下，Ag 2 O或Ag +会促进形成光学活性胺衍生物，或高度非对映异构体过量的二聚体衍生物，其结构通过X射线分析确定。

  DOI：

  10.1016/s0957-4166(00)82009-1

文献信息

• Electrochemical and stereochemical investigation on the mechanism of the decay of 2-halo amide anions. The intermediacy of aziridinones
  作者：Flavio Maran

  DOI：10.1021/ja00068a012

  日期：1993.7

  2-Halo amide anions can be generated by electroreduction of the corresponding NH-protic 2-halo amides through the self-protonation mechanism. Such anions are labile species whose decay, in the case of 2-bromo amide anions, competes with their electroreduction in the voltammetric time scale. Using the appropriate voltammetric treatment, the first-order rate constant of the decay has been determined for a series of representative 2-bromo amides. The lability orders point to an S(N)2-type intramolecular substitution of bromine and thus to the formation of a three-membered ring. Stereochemical information on the decay has been gained using a chiral nonracemic 2-bromopropanamide, an amine nucleophile, and DMF as the solvent. The direct substitution by the amine proceeds by an S(N)2 reaction, as witnessed by inversion of configuration at the alpha-carbon and voltammetric analysis. Conversely, when the reaction is triggered by electroreduction, the decay of the 2-bromo amide anion eventually leads to the formation of the retention product 2-amino amide together with other optically active products, namely two diastereomeric oxazolidin-4-ones, arising by cyclocondensation with DMF, and cis-2,5-dioxopiperazine. Analysis of the electrochemical and stereochemical results indicates that the mechanism of the base-promoted reactions of 2-halo amides proceeds through the transient formation of the corresponding aziridinone, independently of the fact that the latter is isolable or not. The formation of the aziridinone takes place by concerted intramolecular nucleophilic substitution of bromide ion within the 2-halo amide anion. The transient aziridinone behaves not only as the product-determining intermediate but also as a species capable of reacting with suitable partners under remarkable enantioselectivity control.