2-(3,4-二氯苯基)-1H-苯并咪唑 | 67370-32-5

• 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: 2-(3,4-二氯苯基)-1H-苯并咪唑
• 英文名称: 2-(3,4-dichlorophenyl)-1H-benzo[d]imidazole
• 英文别名: 2-(3,4-dichloro-phenyl)-1H-benzoimidazole；2-(3,4-dichlorophenyl)-1H-benzimidazole；2-(3,4-dichlorophenyl)benzimidazole；2-(3,4-dichloro-phenyl)-1H-benzoimidazole；2-(3,4-dichloro-phenyl)-1H-benzimidazole；2-(3,4-Dichlor-phenyl)-1H-benzimidazol
• CAS: 67370-32-5
• 化学式: C₁₃H₈Cl₂N₂
• mdl: MFCD01237666
• 分子量: 263.126
• InChiKey: HFRQRSXRKCUENZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 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：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(3,4-二氯苯基)-1H-苯并咪唑 在 tris-(dibenzylideneacetone)dipalladium(0) 、 BINAP 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 21.0h， 生成 3-{4-[2-(3,4-dichloro-phenyl)-benzoimidazol-1-yl]-pyrimidin-2-ylamino}-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Syntheses and biological evaluation of 1-heteroaryl-2-aryl-1 H -benzimidazole derivatives as c-Jun N-terminal kinase inhibitors with neuroprotective effects

  摘要：

  1-Heteroaryl-2-aryl-1H-benzimidazole derivatives were synthesized as inhibitors of c-Jun N-terminal kinases, JNK3. Their activities were evaluated through measurement of K-d using SPR, JNK3 kinase assay, and cell-viability of human neuroblastoma cells. Most tested compounds showed high affinity (10 mu M-46 nM) to JNK3. Among them, compound 16f exhibited potent activities (K-d = 46 nM). Especially, 16f was also found to present a potent cell protective effect (IC50 = 1.09 mu M) against toxicity induced by anisomycin, showing a possibility as protective therapeutics in neuronal cell apoptosis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.021
• 作为产物：
  描述：

  3,4-二氯苯甲酸 在 三氯异氰尿酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.17h， 生成 2-(3,4-二氯苯基)-1H-苯并咪唑
  参考文献：
  名称：

  三氯异氰尿酸/三苯基膦介导的苯并咪唑，苯并恶唑和苯并噻唑的合成

  摘要：

  从不同的羧酸的反应制备苯并咪唑，苯并恶唑，苯并噻唑和一种新的且有效的方法羧酸与ö苯二胺，ø氨基苯酚，和ö -aminothiophenol在三苯基膦/三氯异氰尿酸体系存在被呈现。根据光谱（红外，NMR，质谱）数据对所需产物进行了表征，并提出了其形成机理。显着的优势是价格低廉且易于获得的试剂，操作简单，条件温和且收率良好至优异。

  DOI：

  10.1071/ch14037

文献信息

• Solvent-dependent metal-free chemoselective synthesis of benzimidazoles and 1,3,5-triarylbenzenes from 2-amino anilines and aryl alkyl ketones catalyzed by I2
  作者：Yuxin Ding、Renchao Ma、Yongmin Ma

  DOI：10.1016/j.tetlet.2021.153016

  日期：2021.4

  the synthesis of benzimidazoles and 1,3,5-triarylbenzenes via the annulation of 2-amino anilines and aryl alkyl ketones or the cyclization of aryl alkyl ketones, respectively. With 1,4-dioxane as the solvent, sequential CN bond formation followed by C(CO)-C(CH3) bond cleavage leads to the formation of benzimidazoles in a highly selective manner while aldol-type self-condensation of aryl alkyl ketones

  开发了一种溶剂依赖性 I2 催化的化学选择性反应，用于分别通过 2-氨基苯胺和芳基烷基酮的环化或芳基烷基酮的环化合成苯并咪唑和 1,3,5-三芳基苯。以 1,4-二恶烷为溶剂，连续形成 CN 键，然后 C（CO）-C（CH3） 键断裂导致以高选择性方式形成苯并咪唑，而使用 PhNO2 或 PhCl 作为溶剂，芳基烷基酮的醛型自缩合占主导地位，得到 1,3,5-三芳基苯。
• Copper-Catalyzed Double C–N Bond Formation for the Synthesis of Diverse Benzimidazoles from N-Alkyl-2-iodoaniline and Sodium Azide
  作者：Zhengkai Chen、Hongjun Ren、Hongli Li、Gangjian Cao、Jianfeng Xu、Maozhong Miao

  DOI：10.1055/s-0036-1588086

  日期：——

  An efficient approach to the synthesis of benzimidazole derivatives has been achieved by copper-catalyzed double C–N bonds formation of N-alkyl-2-iodoaniline and sodium azide. The reaction was supposed to proceed through copper-catalyzed tandem reaction of SNAr reaction, aerobic oxidation of C(sp3)–H bond and intramolecular C–N bond formation sequence. Structurally diverse 2-aryl, alkenyl and alkyl

  通过铜催化 N-烷基-2-碘苯胺和叠氮化钠的双 C-N 键形成，实现了合成苯并咪唑衍生物的有效方法。该反应应该通过铜催化的 SNAr 反应串联反应、C(sp3)-H 键的有氧氧化和分子内 C-N 键形成序列进行。通过这种方法组装了结构多样的 2-芳基、烯基和烷基苯并咪唑衍生物。
• Iron(<scp>ii</scp>) bromide-catalyzed oxidative coupling of benzylamines with ortho-substituted anilines: synthesis of 1,3-benzazoles
  作者：Kovuru Gopalaiah、Sankala Naga Chandrudu

  DOI：10.1039/c4ra12490a

  日期：——

  An iron(II) bromide-catalyzed oxidative coupling of benzylamines with 2-amino/hydroxy/mercapto-anilines has been developed, allowing the synthesis of a diversity of substituted 1,3-benzazoles in good to excellent yields. This transformation is compatible with a wide range of functional groups. The method is practical, economical and employs molecular oxygen as an oxidant.

  已经开发出溴化铁（II）催化的苄胺与2-氨基/羟基/巯基苯胺的氧化偶联，从而可以良好的收率合成各种取代的1,3-苯并唑。此转换与各种功能组兼容。该方法实用，经济并且使用分子氧作为氧化剂。
• Eco-Friendly Synthesis of 2-Substituted Benzimidazoles Using Air as the Oxidant
  作者：Guo-Feng Chen、Hai-Dong Shen、Hui-Ming Jia、Li-Yan Zhang、Hong-Yan Kang、Qing-Qing Qi、Bao-Hua Chen、Jia-Li Cao、Ji-Tai Li

  DOI：10.1071/ch12458

  日期：——

  A simple, environmentally friendly procedure for the synthesis of 2-substituted benzimidazoles by the one-pot condensation of o-phenylenediamines with aromatic aldehydes using continuous bubbling of air in absolute ethanol at room temperature is described. The simplicity of the system, mild conditions, involvement of a non-toxic and practically inexhaustible oxidant, easy and quick isolation of the

  描述了一种简单的，环境友好的方法，该方法通过在室温下在无水乙醇中连续鼓泡使邻苯二胺与芳族醛进行一锅缩合来合成2-取代的苯并咪唑。该方法的主要优点是系统简单，条件温和，涉及无毒且几乎无穷尽的氧化剂，容易，快速地分离出产物以及中等至良好的收率。
• Synthesis of benzimidazole based hydrazones as non‐sugar based α‐glucosidase inhibitors: Structure activity relation and molecular docking
  作者：Muhammad Umair Ahmad、Muhammad Rafiq、Bakhtawar Zahra、Muhamamd Islam、Muhammad Ashraf、Mariya al‐Rashida、Ajmal Khan、Javid Hussain、Zahid Shafiq、Ahmed Al‐Harrasi

  DOI：10.1002/ddr.21807

  日期：2021.11

  search for α-glucosidase inhibitors used in the treatment of diabetes mellitus, a series of unique benzimidazole based hydrazones derivatives were synthesized (5a-5p), which were then investigated for their in vitro α-glucosidase inhibitory potential. The compounds of interest were characterized by modern spectroscopic approaches including CHN, 1HNM R, 13CN MR and FTIR. The structure of compound 5n was distinctively

  为了寻找用于治疗糖尿病的α-葡萄糖苷酶抑制剂，合成了一系列独特的基于苯并咪唑的腙衍生物（5a-5p），然后对其体外α-葡萄糖苷酶抑制潜力进行了研究。感兴趣的化合物通过现代光谱方法进行表征，包括 CHN、1 HNM R、13 CN MR 和 FTIR。化合物5n的结构通过单晶 X 射线研究得到了独特的验证。所有化合物都显示出有效的酶抑制潜力，IC 50值在 2.25 ± 0.01 至 81.16 ± 0.12 μM 范围内，除了显示 IC 50的5n值为 182.75 ± 0.13 μM。有限的结构-活性相关性表明，腙部分中靛红、醛和酮的取代对整体活性有显着贡献，并且在阐明这些化合物在催化位点结合相互作用的机制时进行的分子对接研究进一步支持了这一点α-葡萄糖苷酶。