1-(4-acetylphenyl)-3-phenylpyrrolidine-2,5-dione | 63290-64-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-acetylphenyl)-3-phenylpyrrolidine-2,5-dione
• CAS: 63290-64-2
• 化学式: C₁₈H₁₅NO₃
• 分子量: 293.322
• InChiKey: ZEHIFFCJJUCKKN-UHFFFAOYSA-N

物化性质

• 熔点：
  149-151 °C(Solv: ethanol (64-17-5))
• 沸点：
  573.4±50.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯基丁二酸 、 4-氨基苯乙酮 反应 3.0h， 以29%的产率得到1-(4-acetylphenyl)-3-phenylpyrrolidine-2,5-dione
  参考文献：
  名称：

  Solvatochromic and quantum chemical investigations of newly synthesized succinimides: substituent effect on intramolecular charge transfer

  摘要：

  Two series of 1-aryl-3-phenyl- and 1-aryl-3,3-diphenylpyrrolidine-2,5-diones were synthesized and their solvatochromic properties were studied in a set of 15 solvents of different polarity. The effect of specific and non-specific solvent-solute interactions on the position of their absorption bands was evaluated by using the solvent parameter sets of Kamlet and Taft. The interpretation of the effect of different substituent patterns on the solvatochromic properties of the investigated compounds was based on quantum chemical calculations performed by the density functional theory (DFT)/CAM-B3LYP method using the 6-311G(d,p) basis set. The theoretical absorption frequencies show very good agreement with the experimental values. The energy gaps between the HOMO and LUMO orbitals were also analyzed. It is demonstrated that different substituents change the conjugation effect and further determine the pathways of intramolecular charge transfer.

  DOI：

  10.1007/s00706-013-1052-1