5-amino-1-(p-chlorophenyl)imidazole-4-carbonitrile | 131557-53-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-amino-1-(p-chlorophenyl)imidazole-4-carbonitrile
• 英文别名: 5-amino-1-(4-chlorophenyl)imidazole-4-carbonitrile；5-amino-1-(4-chlorophenyl)-1H-imidazole-4-carbonitrile
• CAS: 131557-53-4
• 化学式: C₁₀H₇ClN₄
• 分子量: 218.645
• InChiKey: DMSFIBPLAJLYIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-amino-1-(p-chlorophenyl)imidazole-4-carbonitrile 在 一水合肼 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 48.0h， 生成 7-(p-chlorophenyl)-1,2,4-triazolo[3,4-i]purine
  参考文献：
  名称：

  Basyouni, W. M.; Hosni, Hanaa M., Egyptian Journal of Chemistry, 2001, vol. 44, # 4-6, p. 251 - 268

  摘要：

  DOI：
• 作为产物：
  描述：

  对氯苯胺 在 氢氧化钾 、 aniline hydrochloride 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 1.0h， 生成 5-amino-1-(p-chlorophenyl)imidazole-4-carbonitrile
  参考文献：
  名称：

  Alves, M. Jose; Booth, Brian L; Al-Duaij, Omar Kh., Journal of Chemical Research, Miniprint, 1993, # 10, p. 2701 - 2719

  摘要：

  DOI：

文献信息

• New application of heterocyclic diazonium salts. Synthesis of pyrazolo[3,4-d][1,2,3]triazin-4-ones and imidazo[4,5-d][1,2,3]triazin-4-ones
  作者：Juan Pablo Colomer、Elizabeth Laura Moyano

  DOI：10.1016/j.tetlet.2011.01.040

  日期：2011.4

  The pyrazolo[3,4-d][1,2,3]triazin-4-ones 3 and imidazo[4,5-d][1,2,3]triazin-4-ones 4 are analogs structurally related to purines that have showed a wide and significant variety of biological activity. These compounds were synthesized by one-pot diazotization of 5-amino-1H-pyrazole-4-carbonitriles 1 and 5-amino-1H-imidazole-4-carbonitriles 2, respectively.

  吡唑并[3,4- d ] [1,2,3] triazin-4-ones 3和咪唑并[4,5- d ] [1,2,3] triazin-4-ones 4是与嘌呤在结构上相关的类似物表现出广泛而显着的生物活性。这些化合物分别通过一锅重氮化5-氨基-1 H-吡唑-4-腈1和5-氨基-1 H-咪唑-4-腈2合成。
• Synthesis of 1-Substituted 5-Aminoimidazole-4-carbaldehydes and 8-Amino-1-(2-fluorobenzyl)imidazo[4’,5’:5,6]pyrido[2,3-<b><i>d</i></b>]pyrimidine
  作者：Brian Booth、Robert Carpenter、Gaby Morlock、Zahid Mahmood、Robin Pritchard

  DOI：10.1055/s-2001-18705

  日期：——

  The syntheses of a number of 1-substituted 5-aminoimidazole-4-carbaldehydes 3, by the reduction of the corresponding 5-amino-4-cyanoimidazole derivatives is reported using LiAlH(OEt)3, prepared in situ from LiAlH4 and ethyl acetate. The compounds of type 1 are useful intermediates for the synthesis of elongated adenine derivatives.

  报道了通过还原相应的5-氨基-4-氰基咪唑衍生物，合成多种1-取代的5-氨基咪唑-4-醛（3），该还原反应使用了由LiAlH4和乙酸乙酯原位制备的LiAlH(OEt)3。类型1的化合物是合成延伸腺苷衍生物的有用中间体。
• Investigation into Sonogashira reaction on 5-iodo-1-(phenyl/<i>p</i>-halophenyl)imidazole-4-carbonitrile compounds
  作者：Aniruddha Das

  DOI：10.1080/00397911.2017.1373298

  日期：2017.12.2

  arbonitrile compounds had been developed by introducing an iodo atom at the C-5 position of the imidazole ring of 5-amino-1-(phenyl/p-halophenyl)imidazole-4-carbonitrile compounds. Specifically, 5-iodo-1-(4-iodophenyl)imidazole-4-carbonitrile compound had shown double Sonogashira coupling reactions with two differently substituted iodine along with the formation of two other compounds where an unusual

  摘要 通过在 5-氨基-1-咪唑环的 C-5 位引入碘原子，对 5-碘-1-(苯基/对-卤代苯基)咪唑-4-甲腈化合物的 Sonogashira 反应进行了研究。 (苯基/对卤苯基)咪唑-4-腈化合物。具体来说，5-iodo-1-(4-iodophenyl)imidazole-4-carbonitrile 化合物与两种不同取代的碘发生双重 Sonogashira 偶联反应，同时形成另外两种化合物，其中获得了一种不寻常的具有自聚集性质的偶联产物. 在其他情况下，观察到单偶联与另一种化合物一起出现，其中存在于咪唑 C5 位置的碘原子被氢原子取代。图形概要
• Synthesis, X-ray crystallographic studies, DFT calculations and nanostructural features of annulated imidazo[4,5-<i>b</i>]pyridine derivatives
  作者：Aniruddha Das

  DOI：10.1080/00397911.2017.1381882

  日期：2017.12.17

  5-b]pyridine. Single X-ray crystallographic diffraction studies had shown that compounds had different types of heterodimeric, homodimeric π–π stacking, T-type stacking, and intermolecular hydrogen bonds which lead to nanostructure formation detected by scanning electron microscope. DFT calculation had also been performed to quantify heterodimeric π–π and T-stacking interactions. GRAPHICAL ABSTRACT

  摘要 5-氨基-4-氰基-1-(苯基/对-取代苯基)咪唑与环烷酮的Friedländer型缩合是通过将混合物与无水氯化铝在干燥的1,2-二氯乙烷中的悬浮液回流以产生7-氨基-3-芳基(5,6)环烷基咪唑并[4,5-b]吡啶。单 X 射线晶体衍射研究表明，化合物具有不同类型的异二聚体、同二聚体 π-π 堆积、T 型堆积和分子间氢键，这导致扫描电子显微镜检测到纳米结构的形成。还进行了 DFT 计算以量化异二聚体 π-π 和 T 堆积相互作用。图形概要
• 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
  作者：Aniruddha Das

  DOI：10.1016/j.molstruc.2017.06.124

  日期：2017.11

  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.