4-((2-phenyl-1H-benzo[d]imidazol-1-yl)methyl)benzonitrile | 1176117-96-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 4-((2-phenyl-1H-benzo[d]imidazol-1-yl)methyl)benzonitrile
• 英文别名: 4-((2-phenyl-1H-benzoimidazol-1-yl)methyl)benzonitrile；4-[(2-phenylbenzimidazol-1-yl)methyl]benzonitrile
• CAS: 1176117-96-6
• 化学式: C₂₁H₁₅N₃
• 分子量: 309.37
• InChiKey: OSRHQPXRALCERW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  41.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 pyridinium chlorochromate 作用下， 以 氯仿 为溶剂， 反应 2.5h， 以86%的产率得到4-((2-phenyl-1H-benzo[d]imidazol-1-yl)methyl)benzonitrile
  参考文献：
  名称：

  PCC-Promoted Dehydration of Aldoximes: A Convenient Access to Aromatic, Heteroaromatic, and Aliphatic Nitriles

  摘要：

  A simple and convenient procedure for the synthesis of nitriles by dehydration of aldoximes using a PCC (pyridiniumchlorochromate) has been developed. A variety of aromatic, heteroaromatic, and aliphatic aldoximes are converted. Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the full spectral details.

  DOI：

  10.1080/00397911.2012.738459

文献信息

• One-pot synthesis of benzimidazoles from gem-dibromomethylarenes using o-diaminoarenes
  作者：Chandrappa Siddappa、Vinaya Kambappa、Ananda Kumar C. Siddegowda、Kanchugarakoppal S. Rangappa

  DOI：10.1016/j.tetlet.2010.09.080

  日期：2010.12

  A one-pot synthesis of benzimidazoles from gem-dibromomethylarenes is described. The reaction shows the method to prepare a variety of benzimidazole analogues with excellent yield.

  描述了从宝石-二溴甲基芳烃一锅合成苯并咪唑。该反应显示出以优异的产率制备各种苯并咪唑类似物的方法。
• Convenient and green synthesis of novel 1,2,5-trisubstituted benzimidazole compounds and their antibacterial activity evaluation
  作者：Kejun Liu、Rui Luo、Jiaxu Fu、Lijian Bao、Yafei Xue、Qiang Gu、Yumin Zhang、Feng Lin

  DOI：10.1007/s13738-022-02736-z

  日期：——

  conditions. Besides, the crystal structure of compound 4c in the orthorhombic space group P 2ac 2ab was presented. Also, the antibacterial activity of the synthesized compounds against Mycobacterium smegmatis in vitro at the cellular level was evaluated using rifampicin as a positive control. Product 4s had the best antibacterial activity among the synthesized compounds and was superior to rifampicin.

  在微波辐射下探索了 1,2,5-三取代苯并咪唑的有效合成。以 2-取代苯并咪唑和 4-取代苄基氯为起始原料，使用 K 2 CO 3作为酸结合剂制备了 20 种新型 1,2,5-三取代苯并咪唑。该方法显示出广泛的底物适应性，并在 15 分钟内以中等到优异的收率提供了目标产物。在获得的最佳反应条件下考察了不同取代基对产率的影响。此外，给出了正交空间群P 2ac 2ab中化合物4c的晶体结构。此外，合成化合物对耻垢分枝杆菌的抗菌活性使用利福平作为阳性对照评估体外细胞水平。产物4s在合成的化合物中抗菌活性最好，优于利福平。
• A Metallaphotoredox Method for the Expansion of Benzyl SAR on Electron-Deficient Amines
  作者：Meghan D. Shea、Umar Faruk Mansoor、Brett A. Hopkins

  DOI：10.1021/acs.orglett.9b04587

  日期：2020.2.7

  A metallaphotoredox reaction is described that allows for the efficient exploration of benzyl structure-activity relationships on electron-deficient amines. Typically, accessing a variety of benzyl groups on these substrates can be difficult due to the limited availability of the prerequisite building blocks, namely benzyl halides. However, the use of aryl bromides in this metallaphotoredox reaction allows for greater diversity in the benzyl piece. The reaction scope is discussed herein, including conditions for product scaleup using flow.
• PCC-Promoted Dehydration of Aldoximes: A Convenient Access to Aromatic, Heteroaromatic, and Aliphatic Nitriles
  作者：S. Chandrappa、T. S. R. Prasanna、K. Vinaya、D. S. Prasanna、K. S. Rangappa

  DOI：10.1080/00397911.2012.738459

  日期：2013.10.18

  A simple and convenient procedure for the synthesis of nitriles by dehydration of aldoximes using a PCC (pyridiniumchlorochromate) has been developed. A variety of aromatic, heteroaromatic, and aliphatic aldoximes are converted. Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the full spectral details.