1-(3-硝基苯基)-1H-苯并[d]咪唑 | 25699-77-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 1-(3-硝基苯基)-1H-苯并[d]咪唑
• 英文名称: N-(3-nitrophenyl) benzimidazole
• 英文别名: 1-(3'-nitrophenyl)benzimidazole；1-(3-nitrophenyl)-1H-benzimidazole；1-(m-Nitrophenyl)benzimidazol；1-(3-Nitrophenyl)-1h-benzo[d]imidazole；1-(3-nitrophenyl)benzimidazole
• CAS: 25699-77-8
• 化学式: C₁₃H₉N₃O₂
• 分子量: 239.233
• InChiKey: YZJZOMBEMQCWAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-硝基苯基)-1H-苯并[d]咪唑 在 palladium 10% on activated carbon 、 甲酸铵 作用下， 以 异丙醇 为溶剂， 生成 3-(1H-苯并[d]咪唑-1-基)苯胺
  参考文献：
  名称：

  Acylthiourea, Acylurea, and Acylguanidine Derivatives with Potent Hedgehog Inhibiting Activity

  摘要：

  The Smoothened (Smo) receptor is the major transducer of the Hedgehog (Hh) signaling pathway. On the basis of the structure of the acylthiourea Smo antagonist (MRT-10), a number of different series of analogous compounds were prepared by ligand-based structural optimization. The acylthioureas, originally identified as actives, were converted into the corresponding acylureas or acylguanidines. In each series, similar structural trends delivered potent compounds with IC50 values in the nanomolar range with respect to the inhibition of the Hh signaling pathway in various cell-based assays and of BODIPY-cyclopamine binding to human Smo. The similarity of their biological activities, in spite of discrete structural differences, may reveal the existence of hydrogen-bonding interactions between the ligands and the receptor pocket. Biological potency of compounds 61, 72, and 86 (MRT-83) were comparable to those of the clinical candidate GDC-0449. These findings suggest that these original molecules will help delineate Smo and Hh functions and can be developed as potential anticancer agents.

  DOI：

  10.1021/jm2013369
• 作为产物：
  描述：

  4,5-Diethynyl-1-(3-nitro-phenyl)-1H-imidazole 在 1,4-环己二烯 作用下， 以 氘代苯 为溶剂， 生成 1-(3-硝基苯基)-1H-苯并[d]咪唑
  参考文献：
  名称：

  咪唑稠合的双炔炔的Bergman环芳烃化：N-芳基取代的显著作用

  摘要：

  制备了一系列的N-芳基取代的“咪唑稠合的”（Z）3-烯-1,5-二炔，并确定了其Bergman环芳化反应活性的动力学参数。N-芳基化相对于N-烷基衍生物的速率提高了七倍（ANOVA p <0.0001）。N-苯基衍生物表现出最大的增强作用（在145°C时为七倍）。

  DOI：

  10.1016/j.tetlet.2004.02.152

文献信息

• Aromatic N-Arylations Catalyzed by Copper-Anchored Porous Zinc-Based Metal-Organic Framework under Heterogeneous Conditions
  作者：Tanmoy Maity、Debraj Saha、Subratanath Koner

  DOI：10.1002/cctc.201400056

  日期：2014.8

  A highly porous Zn‐based metal–organic framework (MOF) IRMOF‐3 was covalently decorated with pyridine‐2‐aldehyde. The free amine group of IRMOF‐3 upon condensation with pyridine‐2‐aldehyde affords a bidentate Schiff‐base moiety in the porous matrix. The Schiff base moieties are availed to anchor copper(II) ions to display the catalyst’s utility towards catalytic reactions. The catalyst was characterized

  高度多孔的锌基金属-有机骨架（MOF）IRMOF-3与吡啶-2-醛共价修饰。与吡啶-2-醛缩合后，IRMOF-3的游离胺基在多孔基质中提供双齿席夫碱部分。席夫碱部分可用于锚定铜（II）离子，以显示催化剂对催化反应的效用。通过紫外/可见光和红外光谱，粉末XRD光谱，SEM能量色散X射线光谱和氮吸附测量对催化剂进行了表征。在Cs 2 CO 3存在下，在温和条件下（90°C），该催化剂在DMSO介质中催化含氮杂环与芳基溴的N-芳基化反应具有出色的催化活性。。由于MOF的孔内存在活性位点，因此多孔催化剂表现出对底物的尺寸选择性。在多达五个连续的催化循环中，锚固的配合物似乎在催化反应过程中不会被浸出或分解，这显示出优于均相催化的实际优势。
• <i>N</i>,<i>O</i>-Bidentate ligand-tunable copper(<scp>ii</scp>) complexes as a catalyst for Chan–Lam coupling reactions of arylboronic acids with 1<i>H</i>-imidazole derivatives
  作者：Xuefeng Jia、Pai Peng

  DOI：10.1039/c8ob02254b

  日期：——

  An efficient procedure for Chan–Lam coupling reactions of arylboronic acids with 1H-imidazole derivatives using N,O-bidentate ligand-tunable copper(II) complexes as a catalyst under base-free conditions has been developed. This protocol features mild reaction conditions, high yields and compatibility with different functional groups, providing a direct and facile strategy for the construction of C–N

  已经开发了一种有效的程序，用于在无碱条件下使用N，O-双齿配体可调铜（II）配合物作为催化剂，使芳基硼酸与1 H-咪唑衍生物进行Chan-Lam偶联反应。该方案具有温和的反应条件，高收率和与不同官能团的相容性，为构建C–N键和合成杂环化合物提供了直接而简便的策略。
• Highly efficient and practical phosphoramidite–copper catalysts for amination of aryl iodides and heteroaryl bromides with alkylamines and N(H)-heterocycles
  作者：Zhanjin Zhang、Jincheng Mao、Di Zhu、Fan Wu、Huilin Chen、Boshun Wan

  DOI：10.1016/j.tet.2006.02.062

  日期：2006.5

  A highly efficient copper-catalyzed system using phosphoramidite as ligands was applied to N-arylation of alkylamines and N(H)-heterocycles with aryl iodides and heteroaryl bromides. The reactions were carried out in relative mild conditions and good to excellent yields were obtained.

  使用亚磷酰胺作为配体的高效铜催化体系被用于烷基胺和N（H）-杂环与芳基碘化物和杂芳基溴化物的N-芳基化反应。反应在相对温和的条件下进行，并获得了良好的产率。
• Cu(<scp>i</scp>) based catalysts derived from bidentate ligands and studies on the effect of substituents for <i>N</i>-arylation of benzimidazoles and indoles
  作者：Sheela Kumari、Anand Ratnam、Kiran Mawai、Virendra Kumar Chaudhary、Aurobinda Mohanty、Kaushik Ghosh

  DOI：10.1039/d0nj02568b

  日期：——

  A family of Cu(I) complexes [Cu(L1–4)(Cl)(PPh3)] (C1–C4) were synthesized from bidentate ligands L1–L4 (where L1 = (E)-2-(2-benzylidene-1-phenylhydrazinyl)pyridine, L2 = (E)-N,N-dimethyl-4-((2-phenyl-2-(pyridin-2-yl)hydrazono)methyl)aniline, L3 = (E)-2-(2-(4-chlorobenzylidene)-1-phenylhydrazinyl)pyridine and L4 = (E)-2-(2-(4-nitrobenzylidene)-1-phenylhydrazinyl)pyridine) and characterized. The structure

  由双齿配体L 1 -L 4（其中L 1 =（E）-2- ）合成Cu（I）配合物家族[Cu（L 1-4）（Cl）（PPh 3）]（C1-C4）（2-亚苄基-1-苯基肼基）吡啶，L 2 =（E）-N，N-二甲基-4-（（2-苯基-2-（吡啶-2-基）肼基）甲基）苯胺，L 3 = （E）-2-（2-（4-氯亚苄基）-1-苯基肼基）吡啶和L 4＝（E）-2-（2-（4-硝基亚苄基）-1-苯基肼基）吡啶）。复合物的结构通过单晶X射线衍射鉴定C1。这些络合物用作苯并咪唑和吲哚的N-芳基化的催化剂。检查了金属配合物配体框架中取代基的作用，并仔细研究了可能的反应途径。
• Immobilization of copper(II) into polyacrylonitrile fiber toward efficient and recyclable catalyst in Chan-Lam coupling reactions
  作者：Chenlu Zhang、Hai Zhu、Kaiyue Gang、Minli Tao、Ning Ma、Wenqin Zhang

  DOI：10.1016/j.reactfunctpolym.2021.104831

  日期：2021.3

  significantly affected by the Cu loading. This catalytic system also displayed good activity in the synthesis of N-arylsulfonamides from arylboronic acids and tosyl azide. It was highly efficient in gram-scale reactions and could be reused five times. The advantages of low cost, easy preparation, good durability and facile recovery make the fiber catalyst attractive.

  通过将Cu（II）固定化为脯氨酰胺改性的PANF（PAN PA-2 F），制备了一系列聚丙烯腈纤维（PANF）负载的铜（II）催化剂，随后将其用于从芳基硼酸中合成各种N-芳基咪唑酸和咪唑。制备的Cu（II）@PAN PA-2 Fs具有良好的机械强度，FT-IR，XRD，XPS和SEM表征。其中，CuCl 2 @PAN PA-2 F表现出优异的催化性能，其活性受到Cu含量的显着影响。该催化体系在合成N中也显示出良好的活性来自芳基硼酸和甲苯磺酰基叠氮化物的-芳基磺酰胺。它在克级反应中非常高效，可以重复使用五次。低成本，易于制备，良好的耐久性和容易回收的优点使纤维催化剂具有吸引力。