2-(benzylamino)-4-(4-bromophenyl)-4-oxo-N-phenylbutanamide | 1638115-40-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(benzylamino)-4-(4-bromophenyl)-4-oxo-N-phenylbutanamide
• CAS: 1638115-40-8
• 化学式: C₂₃H₂₁BrN₂O₂
• 分子量: 437.336
• InChiKey: YOJBYJFJCDWXNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  58.2
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  4-oxo-4-(4-bromo-phenyl)-trans-crotonic acid anilide 、 苄胺 在 sodium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 2-(benzylamino)-4-(4-bromophenyl)-4-oxo-N-phenylbutanamide
  参考文献：
  名称：

  Reactivity of (E)-4-aryl-4-oxo-2-butenoic acid phenylamides with piperidine and benzylamine: kinetic and theoretical study

  摘要：

  Rates of the aza-Michael addition of piperidine and benzylamine to thirteen (E)-4-aryl-4-oxo-2-butenoic acid phenylamides (AACPs) are reported. Progress of the reaction was monitored by UV/Vis spectroscopy. The 2D NMR spectra confirmed regioselectivity of the reactions. Piperidine and benzylamine provide exclusively beta-adducts in respect to the aroyl keto group. Influence of the substituents of the aroyl phenyl ring of AACPs on the rate of the reaction was quantified by Hammett substituent constants, partial atomic charges, and the energies of frontier orbitals. Good correlations between second-order rate constants and the Hammett substituent constants were obtained (r = 0.98, piperidine; r = 0.94, benzylamine) for para-, and meta-, para-substituted derivatives. Best correlations were obtained with the energies of the lowest unoccupied molecular orbitals of compounds, derived from the MP2 level of theory. Calculated UV/Vis spectra of representative AACPs and their Michael adduct with piperidine and benzylamine are in fair agreement with experimentally obtained data.

  DOI：

  10.1007/s00706-014-1223-8