2-(2'-fluorophenyl)-7-methyl-1H-benzo[d]imidazole

• 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: 2-(2'-fluorophenyl)-7-methyl-1H-benzo[d]imidazole
• 英文别名: 2-(2-fluorophenyl)-7-methyl-1H-benzimidazole；2-(2-Fluorophenyl)-4-methyl-1h-benzimidazole
• 化学式: C₁₄H₁₁FN₂
• mdl: MFCD11849227
• 分子量: 226.253
• InChiKey: GUBMXVLUWDPKSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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

• 作为反应物：
  描述：

  2-(2'-fluorophenyl)-7-methyl-1H-benzo[d]imidazole 在 copper(II) bis(trifluoromethanesulfonate) sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 21.0h， 生成 6-tert-butyl-11-methyl-6,7-dihydro-5-oxa-7a,12-diazadibenzo[a,e]azulene
  参考文献：
  名称：

  苯并咪唑活化的硝基的分子内芳香亲核取代。

  摘要：

  各种2-（2-硝基苯基）-1H-苯并咪唑在温和的条件下（DMF，rt）经历高产率的亚硝酸盐分子内S（N）Ar与N-侧链醇盐的结合。当此操作简单的过程在过量的NaH存在下于高温下进行时，最初形成的S（N）Ar产物会通过碱转化为相应的N-乙烯基取代的2-（2-羟苯基）-1H-苯并咪唑-催化的异构化。[反应：看文字]

  DOI：

  10.1021/ol035761w
• 作为产物：
  描述：

  邻氟苯甲酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 生成 2-(2'-fluorophenyl)-7-methyl-1H-benzo[d]imidazole
  参考文献：
  名称：

  苯并咪唑活化的硝基的分子内芳香亲核取代。

  摘要：

  各种2-（2-硝基苯基）-1H-苯并咪唑在温和的条件下（DMF，rt）经历高产率的亚硝酸盐分子内S（N）Ar与N-侧链醇盐的结合。当此操作简单的过程在过量的NaH存在下于高温下进行时，最初形成的S（N）Ar产物会通过碱转化为相应的N-乙烯基取代的2-（2-羟苯基）-1H-苯并咪唑-催化的异构化。[反应：看文字]

  DOI：

  10.1021/ol035761w

文献信息

• Nickel-Catalyzed C–F/N–H Annulation of 2-(2-Fluoroaryl) N-Heteroaromatic Compounds with Alkynes: Activation of C–F Bonds
  作者：Naoto Chatani、Haruka Kawakami、Itsuki Nohira

  DOI：10.1055/a-1337-5504

  日期：2021.9

  The reaction of 2-(2-fluoroaryl) N-heteroaromatic compounds, such as benzimidazole and indole derivatives, with internal alkynes in the presence of a catalytic amount of a nickel complex results in C–F/N–H annulation with alkynes. The reaction shows a high functional group compatibility. The presence of a strong base, such as KOBu­ t or LiOBu t , is required for the reaction to proceed.

  在存在少量镍配合物的情况下，2-(2-氟芳基)N-杂环化合物（如苯并咪唑和吲哚衍生物）与内部炔烃发生反应，发生C-F/N-H与炔烃的环化。该反应显示出高的官能团兼容性。需要强碱存在，如KOBu­或LiOBu­t，才能使反应进行。

• Intermolecular SNAr of the heterocycle-activated nitro and fluoro groups-application in the synthesis of polyazamacrocyclic ligands
  申请人：Chan K. Michael

  公开号：US20050239767A1

  公开（公告）日：2005-10-27

  A new class of tetracylic benzimidazole compounds and derivatives thereof. Additionally provided is a synthetic route for the generation of these and related compounds via Intramolecular Aromatic Nucleophilic Substitution (S N Ar) of the Benzimidazole-Activated Nitro Groups. Additionally, a facile route for the generation of novel phenol species as thermal decomposition of compounds the S N Ar product, which occurs at high temperature resulting in cleavage of the ether linkage and formation of a vinyl group and phenol is provided. Also provided are methods of using the compounds described herein in the treatment HIV.

  一类新的四环苯并咪唑化合物及其衍生物。此外，还提供了一种合成途径，通过苯并咪唑活化的硝基基团的分子内芳香亲核取代（SNAr）生成这些相关化合物。此外，还提供了一种简便的途径，通过化合物SNAr产物的热分解，在高温下发生醚键的断裂和乙烯基团和酚的形成，生成新型酚类物种。还提供了使用本文所述化合物治疗HIV的方法。
• Synthesis, α-glucosidase inhibitory, cytotoxicity and docking studies of 2-aryl-7-methylbenzimidazoles
  作者：Muhammad Taha、Nor Hadiani Ismail、Syahrul Imran、Muhammad Helmi Mohamad、Abdul Wadood、Fazal Rahim、Syed Muhammad Saad、Ashfaq ur Rehman、Khalid Mohammed Khan

  DOI：10.1016/j.bioorg.2016.02.004

  日期：2016.4

  Benzimidazole analogs 1-27 were synthesized, characterized by EI-MS and H-1 NMR and their alpha-glucosidase inhibitory activities were found out experimentally. Compound 25, 19, 10 and 20 have best inhibitory activities with IC50 values 5.30 +/- 0.10, 16.10 +/- 0.10, 25.36 +/- 0.14 and 29.75 +/- 0.19 respectively against alpha-glucosidase. Compound 6 and 12 has no inhibitory activity against alpha-glucosidase enzyme among the series. Further studies showed that the compounds are not showing any cytotoxicity effect. The docking studies of the compounds as well as the experimental activities of the compounds correlated well. From the molecular docking studies, it was observed that the top ranked conformation of all the compounds fit well in the active site of the homology model of alpha-glucosidase. (C) 2016 Elsevier Inc. All rights reserved.
• BENZIMIDAZOLES USEFUL AS MODULATORS OF ION CHANNELS
  申请人：Wilson Dean M.

  公开号：US20080306129A1

  公开（公告）日：2008-12-11

  The present invention relates to compounds of Formula I: or a pharmaceutically acceptable salt thereof, wherein the R 1 , Z, Y, R A , and W groups of formula I are as defined herein. The invention also provides pharmaceutically acceptable compositions and methods of using the compositions in the treatment of various disorders.
• US7309716B2
  申请人：——

  公开号：US7309716B2

  公开（公告）日：2007-12-18