1-benzyl-5-cyanoimidazole | 914781-69-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-benzyl-5-cyanoimidazole
• 英文别名: 3-Benzylimidazole-4-carbonitrile
• CAS: 914781-69-4
• 化学式: C₁₁H₉N₃
• 分子量: 183.213
• InChiKey: IQBAPOBQDAEYAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  41.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-5-cyanoimidazole 在 盐酸羟胺 、 sodium carbonate 作用下， 以 水 为溶剂， 反应 5.0h， 以77%的产率得到1-benzylimidazole-5-carboxamide oxime
  参考文献：
  名称：

  Synthesis, ocular effects, and nitric oxide donation of imidazole amidoximes

  摘要：

  Novel 1-R-imidazole-5-amidoximes and I-R-5-cyano-imidazole-4-amidoximes (R: H, Me, Bn) were prepared from their corresponding nitriles and were tested for their efficacy to lower intraocular pressure (IOP) in rabbits. The ability of these compounds to donate nitric oxide (NO) was studied by observing the stimulation of formation of cyclic guanosine-3',5'-monophosphate (cGMP) in the incubation of porcine iris-ciliary body. In the incubation experiments, 1-methylimidazole-5-amidoxime and 1(H)-imidazole-4(5)-amidoxime stimulated formation of cGMP indicating NO donating ability of these compounds. 1-Methylimidazole-5-amidoxime lowered IOP significantly after intravitreal injection. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.05.001
• 作为产物：
  描述：

  (E/Z)-1-benzylimidazole-5-carbaldehyde oxime 在 乙酸酐 作用下， 反应 18.0h， 以44%的产率得到1-benzyl-5-cyanoimidazole
  参考文献：
  名称：

  Synthesis, ocular effects, and nitric oxide donation of imidazole amidoximes

  摘要：

  Novel 1-R-imidazole-5-amidoximes and I-R-5-cyano-imidazole-4-amidoximes (R: H, Me, Bn) were prepared from their corresponding nitriles and were tested for their efficacy to lower intraocular pressure (IOP) in rabbits. The ability of these compounds to donate nitric oxide (NO) was studied by observing the stimulation of formation of cyclic guanosine-3',5'-monophosphate (cGMP) in the incubation of porcine iris-ciliary body. In the incubation experiments, 1-methylimidazole-5-amidoxime and 1(H)-imidazole-4(5)-amidoxime stimulated formation of cGMP indicating NO donating ability of these compounds. 1-Methylimidazole-5-amidoxime lowered IOP significantly after intravitreal injection. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.05.001

文献信息

• Regiochemistry of N-substitution of some 4(5)-substituted imidazoles under solvent-free conditions
  作者：Larisa Oresmaa、Helena Taberman、Matti Haukka、Pirjo Vainiotalo、Paula Aulaskari

  DOI：10.1002/jhet.5570440632

  日期：2007.11

  Imidazole-4(5)-carboxaldehyde and 4(5)-cyanoimidazole were N-benzylated and N-methylated using benzyl chloride and methyl iodide on zinc oxide (ZnO), alumina, and KF/alumina under basic conditions without solvent. Triethylamine (Et3N) or potassium carbonate was added as base in the reactions on ZnO and alumina. Imidazole-4(5)-carboxaldehyde was also benzylated on silica and carbon nanotubes. The effect

  在碱性条件下，在无溶剂的情况下，使用苄基氯和甲基碘在氧化锌（ZnO），氧化铝和KF /氧化铝上对N-苄基化和N-甲基化咪唑4（5）-甲醛和4（5）-氰基咪唑。在ZnO和氧化铝上的反应中，加入三乙胺（Et 3 N）或碳酸钾作为碱。咪唑-4（5）-甲醛在二氧化硅和碳纳米管上也被苄基化。研究了碱和固体对1,4-和1,5-取代的化合物的产物分布的影响。在某些情况下，咪唑-4（5）-甲醛和4（5）-氰基咪唑的产物比率不同。在KF /氧化铝上的反应中，两种化合物都偏爱1,4-产物。Et 3的组合N和ZnO有利于1,5-产物，但是腈的作用并不那么明显。当在催化量的氯化锌以Et 3 N为碱的条件下进行醛的N-苄基化和甲基化时，产物分布与在ZnO上的反应相同。在ZnCl 2存在下，腈在ZnO上给出不同的产物比率。另外，当咪唑在KF /氧化铝上被苄基化时，产生了N-苄基咪唑和1，3-二苄基咪唑的混合物。当使用两当量的苄基氯时，仅提供后者的产物。
• Synthesis, ocular effects, and nitric oxide donation of imidazole amidoximes
  作者：L. Oresmaa、H. Kotikoski、M. Haukka、O. Oksala、E. Pohjala、H. Vapaatalo、E. Moilanen、P. Vainiotalo、P. Aulaskari

  DOI：10.1016/j.ejmech.2006.05.001

  日期：2006.9

  Novel 1-R-imidazole-5-amidoximes and I-R-5-cyano-imidazole-4-amidoximes (R: H, Me, Bn) were prepared from their corresponding nitriles and were tested for their efficacy to lower intraocular pressure (IOP) in rabbits. The ability of these compounds to donate nitric oxide (NO) was studied by observing the stimulation of formation of cyclic guanosine-3',5'-monophosphate (cGMP) in the incubation of porcine iris-ciliary body. In the incubation experiments, 1-methylimidazole-5-amidoxime and 1(H)-imidazole-4(5)-amidoxime stimulated formation of cGMP indicating NO donating ability of these compounds. 1-Methylimidazole-5-amidoxime lowered IOP significantly after intravitreal injection. (c) 2006 Elsevier SAS. All rights reserved.