5-(4-pyridyl)-5-phenylhydantoin | 54743-30-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5-(4-pyridyl)-5-phenylhydantoin
• 英文别名: 5-phenyl-5-(pyridin-4-yl)imidazolidine-2,4-dione；5-phenyl-5-[4]pyridyl-imidazolidine-2,4-dione；5-Phenyl-5-[4]pyridyl-imidazolidin-2,4-dion；5-phenyl-5-pyridin-4-ylimidazolidine-2,4-dione
• CAS: 54743-30-5
• 化学式: C₁₄H₁₁N₃O₂
• 分子量: 253.26
• InChiKey: VYUUHZBFLMZUHW-UHFFFAOYSA-N

物化性质

• 熔点：
  253-255 °C
• 密度：
  1.306±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  71.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  溴代异丁烷 、 5-(4-pyridyl)-5-phenylhydantoin 在 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以84%的产率得到3-isobutyl-5-phenyl-5-(pyridin-4-yl)imidazolidine-2,4-dione
  参考文献：
  名称：

  Synthesis, structural exploration, spectral and combinatorial analysis of racemic-3-isobutyl-5-phenyl-5-(pyridin-4-yl)imida-zolidine-2,4-dione: Comparison between experimental and DFT calculations

  摘要：

  New racemic 3-isobutyl-5-phenyl-5-(pyridin-4-yl)imidazolidine-2,4-dione was synthesized, isolated, characterized spectrally, thermally and finally the structure was confirmed by X-ray diffraction studies. Both XRD and DFT/B3LYP/6-31G(d,p) optimized structures of the compound revealed the diketo monomer as favored tautomer isomer structure. The molecular geometry optimization parameters were compared with the experimental XRD results. The electronic spectrum which allocated basis of the TD-SCF result and the MO energy level diagram were compared with the experimental one. The electrophilic and nucleophilic receptors and acceptor functional groups with their interactions on the molecule surface was established by packing diagrams and then compared with Hirshfeld surface, electrostatic potential map and Mullikan population theoretical calculations. The experimental H-1 NMR results, compared to the theoretical ACD-lab and NMR-db showed an excellent agreement. The desired organic compound revealed a high thermal stability in an open atmosphere. (C) 2018 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2018.04.096
• 作为产物：
  描述：

  氰化钠 、 4-苯甲酰吡啶 在 ammonium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以47%的产率得到5-(4-pyridyl)-5-phenylhydantoin
  参考文献：
  名称：

  5-(4-Pyridyl)-5-phenylhydantoin

  摘要：

  The structure of the title compound, C14H11N3O2, is reported. The hydantoin ring is nearly planar. Bond distances and angles within the hydantoin ring are similar to those of the known 5,5-diphenylhydantoin. The angles between the hydantoin and the phenyl and pyridyl rings are very unequal, unlike those in 5,5-diphenylhydantoin. There is an intermolecular hydrogen-bonding network involving the amido H atoms as donors and the pyridyl-N atom and one carbonyl-O atom as accepters; there is no intramolecular hydrogen bonding.

  DOI：

  10.1107/s0108270198014528

文献信息

• US3994904A
  申请人：——

  公开号：US3994904A

  公开（公告）日：1976-11-30
• US4061760A
  申请人：——

  公开号：US4061760A

  公开（公告）日：1977-12-06