2-(4-chloro-2-fluorophenyl)-1H-benzimidazole | 1081112-49-3

• 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-(4-chloro-2-fluorophenyl)-1H-benzimidazole
• CAS: 1081112-49-3
• 化学式: C₁₃H₈ClFN₂
• mdl: MFCD11645341
• 分子量: 246.671
• InChiKey: OSFUSPFNVMEFMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：
  2

反应信息

• 作为反应物：
  描述：

  3-[4-(3-acetylaminophenyl)piperidin-1-yl]propyl methanesulfonate 、 2-(4-chloro-2-fluorophenyl)-1H-benzimidazole 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以93 mg的产率得到2-(4-chloro-2-fluorophenyl)-1-{3-[4-(3-acetylaminophenyl)piperidin-1-yl]propyl}-1H-benzimidazole
  参考文献：
  名称：

  Synthesis and SAR investigations of novel 2-arylbenzimidazole derivatives as melanin-concentrating hormone receptor 1 (MCH-R1) antagonists

  摘要：

  Compounds containing 2-arybenzimidazole ring systems linked to arylpiperidines were synthesized and evaluated as MCH-R1 antagonists. The results of structure-activity relationship studies led to the identification of compound 4c as a potent MCH-R1 antagonist (IC50 = 1 nM). This compound also has good metabolic stability, and favorable pharmacokinetic and brain penetration properties. However 4c was found to be potent inhibitor of the hERG potassium channel. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.099
• 作为产物：
  描述：

  邻苯二胺 、 4-氯-2-氟苯甲酸 在 polyphosphoric acid 作用下， 反应 4.0h， 生成 2-(4-chloro-2-fluorophenyl)-1H-benzimidazole
  参考文献：
  名称：

  Synthesis and SAR investigations of novel 2-arylbenzimidazole derivatives as melanin-concentrating hormone receptor 1 (MCH-R1) antagonists

  摘要：

  Compounds containing 2-arybenzimidazole ring systems linked to arylpiperidines were synthesized and evaluated as MCH-R1 antagonists. The results of structure-activity relationship studies led to the identification of compound 4c as a potent MCH-R1 antagonist (IC50 = 1 nM). This compound also has good metabolic stability, and favorable pharmacokinetic and brain penetration properties. However 4c was found to be potent inhibitor of the hERG potassium channel. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.099

文献信息

• Ru(II)-Catalyzed C–H Functionalization of 2-Arylbenzimidazoles with Iodonium Ylides: A Straightforward Access to Bridgehead Polycyclic N-Heterocycles
  作者：Saiprasad Nunewar、Sanjeev Kumar、Akhilesh Waman Meshram、Vinaykumar Kanchupalli

  DOI：10.1021/acs.joc.2c01429

  日期：2022.11.4

  rylimidazoles with iodonium ylides leading to substituted tetracyclic and pentacyclic bridgehead N-heterocycles, wherein iodonium ylide acts as a carbene precursor. For the first time, iodonium ylide proceeds through a Ru–carbenoid intermediate. Further, the synthetic utility of this protocol was successfully shown for gram-scale synthesis and useful synthetic transformations.

  在此，我们公开了一种有效的钌催化的 2-芳基苯并咪唑/2-芳基咪唑与碘鎓叶立德的 C-H 官能化，产生取代的四环和五环桥头 N-杂环，其中碘鎓叶立德作为卡宾前体。碘鎓叶立德第一次通过 Ru-carbenoid 中间体进行。此外，该协议的合成效用成功地展示了克级合成和有用的合成转换。
• US8198307B2
  申请人：——

  公开号：US8198307B2

  公开（公告）日：2012-06-12
• Synthesis and SAR investigations of novel 2-arylbenzimidazole derivatives as melanin-concentrating hormone receptor 1 (MCH-R1) antagonists
  作者：Chae Jo Lim、Nakjeong Kim、Eun Kyoung Lee、Byung Ho Lee、Kwang-Seok Oh、Sung-eun Yoo、Kyu Yang Yi

  DOI：10.1016/j.bmcl.2011.02.099

  日期：2011.4

  Compounds containing 2-arybenzimidazole ring systems linked to arylpiperidines were synthesized and evaluated as MCH-R1 antagonists. The results of structure-activity relationship studies led to the identification of compound 4c as a potent MCH-R1 antagonist (IC50 = 1 nM). This compound also has good metabolic stability, and favorable pharmacokinetic and brain penetration properties. However 4c was found to be potent inhibitor of the hERG potassium channel. (C) 2011 Elsevier Ltd. All rights reserved.