1-phenyl-5-aminoimidazole-4-carboxamide | 64995-55-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-phenyl-5-aminoimidazole-4-carboxamide
• 英文别名: 5-Amino-1-phenyl-1H-imidazole-4-carboxamide；5-amino-1-phenylimidazole-4-carboxamide
• CAS: 64995-55-7
• 化学式: C₁₀H₁₀N₄O
• 分子量: 202.216
• InChiKey: YZCLJSGEGBGEGP-UHFFFAOYSA-N

物化性质

• 熔点：
  190-194 °C
• 沸点：
  464.3±25.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-phenyl-5-aminoimidazole-4-carboxamide 在 三氯氧磷 作用下， 反应 3.0h， 生成 6-氯-9-苯基嘌呤
  参考文献：
  名称：

  El-Bayouki, Khairy A. M.; El-Sayed, Ali S.; Basyouni, Whaid M., Gazzetta Chimica Italiana, 1989, vol. 119, # 3, p. 163 - 166

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氰基-2-(乙氧基亚甲基氨基)乙酰胺 、 苯胺 反应 0.5h， 以59.4%的产率得到1-phenyl-5-aminoimidazole-4-carboxamide
  参考文献：
  名称：

  Studies on complex π-π and T-stacking features of imidazole and phenyl/p-halophenyl units in series of 5-amino-1-(phenyl/p-halophenyl)imidazole-4-carboxamides and their carbonitrile derivatives: Role of halogens in tuning of conformation

  摘要：

  5-amino-1-(phenyl/p-halophenyl)imidazole-4-carboxamides (N-phenyl AICA) (2a-e) and 5-amino-1-(phenyl/p-halophenyl)imidazole-4-carbonitriles (N-phenyl AICN) (3a-e) had been synthesized. X-ray crystallographic studies of 2a-e and 3a-e had been performed to identify any distinct change in stacking patterns in their crystal lattice. Single crystal X-ray diffraction studies of 2a-e revealed pi-pi stack formations with both imidazole and phenyl/p-halophenyl units in anti and syn parallel-displaced (PD)-type dispositions. No pi-pi stacking of imidazole occurred when the halogen substituent is bromo or iodo; pi-pi stacking in these cases occurred involving phenyl rings only. The presence of an additional T-stacking had been observed in crystal lattices of 3a-e. Vertical pi-pi stacking distances in anti-parallel PD-type arrangements as well as T-stacking distances had shown stacking distances short enough to impart stabilization whereas syn-parallel stacking arrangements had got much larger pi-pi stacking distances to belie any syn-parallel stacking stabilization. DFT studies had been pursued for quantifying the pi-pi stacking and T-stacking stabilization. The plotted curves for anti-parallel and T-stacked moieties had similarities to the 'Morse potential energy curve for diatomic molecule'. The minima of the curves corresponded to the most stable stacking distances and related energy values indicated stacking stabilization. Similar DFT studies on syn-parallel systems of 2b corresponded to no pi-pi stacking stabilization at all. Halogen-halogen interactions had also been observed to stabilize the compounds 2d, 2e and 3d. Nano-structural behaviour of the series of compounds 2a-e and 3a-e were thoroughly investigated. (C) 2017 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2017.06.124

文献信息

• Preparation and Characterization of Some Metal Chelates of 5-Amino-1-(Aryl)-Imidazole-4-Carboxamide
  作者：Nabil S. Youssef、Wahid M. Basyouni

  DOI：10.1080/00945719909349522

  日期：1999.8

  Cu(II), Cr(III), VO(II) and Mn(II) chelates of 5-amino-1-(aryl)imidazole-4-carboxamide, aryl = C6H5-, -C6H4CH3, and -C6H4OCH3 were prepared and characterized by microchemical analyses, infrared and electronic spectra and thermogravimetric analyses. IR spectra showed that the ligands behave in a bidentate manner. Also, octahedral structures are proposed for the Cr(III) and Mn(II) chelates, whereas square-planar and square-pyramidal structures are proposed for the Cu(II) and oxovanadium(IV) chelates, respectively.
• PREPARATION AND STRUCTURAL STUDIES ON METAL COMPLEXES OF SOME CARBOXAMIDES
  作者：Ali E. Eid

  DOI：10.1081/sim-100105256

  日期：2001.6.30

  Transition metal [Pt(IV), Fe(III), Co(II) and Ni(II)] complexes of 5-amino-1-(aryl)imidazole-4-carboxamide (aryl = C6H5, C6H4CH3 and C6H4-OCH3) were prepared and characterized by microchemical analyses, infrared, electronic spectra and thermogravimetric analyses. The infrared spectra showed that these ligands coordinate to metal ions in a bidentate manner. Moreover, octahedral structures are suggested for all the studied complexes.
• Chattopadhyay, Gautam; Saha, Tapas K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 4, p. 827 - 830
  作者：Chattopadhyay, Gautam、Saha, Tapas K.

  DOI：——

  日期：——
• Synthesis of crown containing imidazo[4,5-e] and-[5,4-e][1,4]diazepines
  作者：É. I. Ivanov

  DOI：10.1007/bf02252284

  日期：1998.6
• Synthesis of crown-containing xanthine derivatives
  作者：E. I. Ivanov、A. A. Polishchuk、G. D. Kalayanov

  DOI：10.1007/bf00531490

  日期：1992.9