6-fluoro-2-(p-tolyl)-1H-benzo[d]imidazole | 79529-99-0

• 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: 6-fluoro-2-(p-tolyl)-1H-benzo[d]imidazole
• 英文别名: 2-(p-Tolyl)-6-fluoro-1H-benzoimidazole；6-fluoro-2-(4-methylphenyl)-1H-benzimidazole
• CAS: 79529-99-0
• 化学式: C₁₄H₁₁FN₂
• mdl: MFCD20146582
• 分子量: 226.253
• InChiKey: FSIDFHNIFHTTFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-fluoro-N-[(E)-(4-methylphenyl)methylideneamino]aniline 以7%的产率得到
  参考文献：
  名称：

  ROBEV, S. K., DOKL. BOLG. AN, 1981, 34, N 5, 663-666

  摘要：

  DOI：

文献信息

• Benzimidazoles from Aryl Alkyl Ketones and 2-Amino Anilines by an Iodine Catalyzed Oxidative C(CO)–C(alkyl) Bond Cleavage
  作者：Owk Ravi、Altab Shaikh、Atul Upare、Kiran Kumar Singarapu、Surendar Reddy Bathula

  DOI：10.1021/acs.joc.7b00165

  日期：2017.4.21

  Novel molecular iodine catalyzed cyclization reactions of 2-amino anilines with aryl alkyl ketones under oxidant and metal-free conditions are described. The reaction likely involves sequential C–N bond formation followed by C(CO)–C(alkyl) bond cleavage. Various 2-substituted benzimidazoles are obtained in moderate to good yields in a single step from readily available acetophenones, propiophenones

  描述了在氧化剂和无金属条件下2-氨基苯胺与芳基烷基酮的新型分子碘催化的环化反应。该反应可能涉及顺序形成C–N键，然后裂解C（CO）–C（烷基）键。从容易获得的苯乙酮，苯乙酮和苯乙酮中一步即可以中等到良好的收率获得各种2-取代的苯并咪唑。
• Benzimidazoles and benzothiazoles from styrenes and N-vinylimidazole via palladium catalysed oxidative C C and C N bond cleavage
  作者：Altab Shaikh、Owk Ravi、S. Pushpa Ragini、Nimma Sadhana、Surendar Reddy Bathula

  DOI：10.1016/j.tetlet.2019.151356

  日期：2020.1

  Herein we report a first, palladium catalyzed, one-pot methodology for the synthesis of pharmacologically important benzimidazoles and benzothiazoles from readily available terminal aromatic olefins. The process involves sequential C=C/C-N bond cleavage followed by C−N/C−S bond formation.

  在本文中，我们报道了一种由钯催化的单罐方法，该方法可从易于获得的末端芳族烯烃中合成具有药理学意义的重要苯并咪唑和苯并噻唑。该过程涉及顺序的C = C / CN键裂解，然后形成CN / CS键。
• Inexpensive Weight-Reducing Aid (L-Carnitine) as An Efficient Catalyst for Synthesis of Benzimidazoles
  作者：Min Zhang、Guoling Huang、Xuefang Zhang、Zhenyuan Lin、Yibiao Li、Bin Li、Lu Chen

  DOI：10.2174/1386207321666181018163940

  日期：2018.12.17

  yields. MATERIALS AND METHODS Melting points were measured on an Electrothemal X6 microscopy digital melting point apparatus. 1H NMR and 13C NMR spectra were recorded in DMSO-d6 on a Bruker AVANCE 400 (400 MHz) instrument with the TMS at d 0.00 ppm as an internal standard. C, H and N analysis were performed by a Perkin-Elmer 2400 CHN elemental analyzer. Chemicals used were of commercial grade without further

  目的和目的通过廉价的减重助剂（L-肉碱）获得苯并咪唑衍生物。各种芳香醛在温和条件下容易与取代的邻苯二胺缩合，以优异的收率得到目标分子。材料与方法熔点是在Electrothemal X6显微镜数字熔点仪上测量的。在DMSO-d6中在Bruker AVANCE 400（400MHz）仪器上用TMS以d 0.00 ppm作为内标记录了1 H NMR和13 C NMR谱。C，H和N分析是通过Perkin-Elmer 2400 CHN元素分析仪进行的。所使用的化学试剂为工业级，无需进一步纯化。邻苯二胺1，芳香醛2的等摩尔（1.0 mmol）混合物 将L-肉碱（10mol％）在EtOH（3mL）中在60℃下剧烈搅拌TLC指示的特定时间（石油：乙酸乙酯＝ 4∶1）。反应完成后，通过加入H 2 O（20mL）淬灭混合物，用EtOAc（3×10mL）萃取，合并的萃取液用无水MgSO 4干燥。蒸发滤液，得到相
• Copper(I)-Catalyzed Regioselective Amination of <i>N</i>-Aryl Imines Using TMSN₃ and TBHP: A Route to Substituted Benzimidazoles
  作者：Devulapally Mahesh、Pradeep Sadhu、Tharmalingam Punniyamurthy

  DOI：10.1021/jo502574u

  日期：2015.2.6

  efficient copper-catalyzed amination of N-aryl imines is described. This one-pot, multicomponent reaction, in which imine acts as a directing group by chelating to the metal center, affords a potential route for the transformation of the commercial aryl amines, aldehydes, and azides into valuable benzimidazole structural units with wide substrate scope and diversity. The synthetic and mechanistic aspects

  描述了新颖和有效的铜催化的N-芳基亚胺的胺化。这种单锅多组分反应（其中亚胺通过与金属中心的螯合而充当导向基团）提供了潜在的途径，可将商业化的芳基胺，醛和叠氮化物转化为有价值的苯并咪唑结构单元，具有广泛的底物范围和多样性。提出了综合和机制方面。
• Transition-Metal-Free Transfer Hydrogenative Cascade Reaction of Nitroarenes with Amines/Alcohols: Redox-Economical Access to Benzimidazoles
  作者：Arup K. Kabi、Raghuram Gujjarappa、Anupam Roy、Abhishek Sahoo、Dulal Musib、Nagaraju Vodnala、Virender Singh、Chandi C. Malakar

  DOI：10.1021/acs.joc.1c01450

  日期：2021.11.5

  describes an efficient transition-metal-free process toward the transfer hydrogenative cascade reaction between nitroarenes and amines or alcohols. The developed redox-economical approach was realized using a combination of KOtBu and Et3SiH as reagents, which allows the synthesis of benzimidazole derivatives via σ-bond metathesis. The reaction conditions hold well over a wide range of substrates embedded with

  该报告描述了一种有效的无过渡金属工艺，用于硝基芳烃与胺或醇之间的转移氢化级联反应。开发的氧化还原经济方法是使用 KO t Bu 和 Et 3 SiH 作为试剂的组合实现的，这允许通过 σ 键复分解合成苯并咪唑衍生物。反应条件适用于各种嵌入不同官能团的底物，以良好至优异的产率提供所需的产品。已根据一系列控制实验、质谱证据描述了机械建议，这些证据得到了具有可行能量分布的密度泛函理论 (DFT) 计算的充分支持。