2-(3-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole | 400073-80-5

• 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-(3-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole
• 英文别名: 2-(3-(trifluoromethyl)phenyl)-1H-benzimidazole；2-[3-(Trifluoromethyl)phenyl]-1H-benzimidazole
• CAS: 400073-80-5
• 化学式: C₁₄H₉F₃N₂
• mdl: MFCD02656543
• 分子量: 262.234
• InChiKey: SPOLNBHTSVLAJW-UHFFFAOYSA-N

物化性质

• 沸点：
  395.8±52.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole 、 3-[4-(3-acetylaminophenyl)piperidin-1-yl]propyl methanesulfonate 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以290 mg的产率得到2-(3-trifluoromethylphenyl)-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 、 间三氟甲基苯乙酮 在 碘 、 二甲基亚砜 、 sodium sulfate 作用下， 反应 12.0h， 以62%的产率得到2-(3-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  碘催化氧化C（CO）-C（烷基）键裂解芳烷基酮和2-氨基苯胺中的苯并咪唑

  摘要：

  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。

  DOI：

  10.1021/acs.joc.7b00165

文献信息

• Aerobic Oxidation of Primary Amines to Imines in Water using a Cobalt Complex as Recyclable Catalyst under Mild Conditions
  作者：Susanta Hazra、Priti Pilania、Mayukh Deb、Ajay Kishor Kushawaha、Anil J. Elias

  DOI：10.1002/chem.201803251

  日期：2018.10.22

  Oxidative coupling of primary amines to imines has been achieved by using a water soluble cobalt complex as catalyst and air as the oxidant at near ambient conditions. Aromatic, heteroaromatic and aliphatic amines were successfully converted to the corresponding imines with yields of up to 96 %. A 20 gram scale reaction for the synthesis of imine from benzylamine in good yield is also demonstrated

  伯胺与亚胺的氧化偶联已通过在近乎环境条件下使用水溶性钴配合物作为催化剂并使用空气作为氧化剂来实现。芳香族，杂芳香族和脂肪族胺已成功转化为相应的亚胺，产率高达96％。用该方法还证明了20克规模的反应，用于从苄胺以高收率合成亚胺。已经发现该催化剂可重复使用多达五个循环。它高效，周转率（TON）高达128，并显示化学选择性，唯一的副产物是水和氨。对照实验和机理研究表明，Co II / Co III催化循环负责这些氧化转化。该反应的一些反应性中间体也已经被分离和结构表征。
• Azaruthena(II)‐bicyclo[3.2.0]heptadiene: Key Intermediate for Ruthenaelectro(II/III/I)‐catalyzed Alkyne Annulations
  作者：Long Yang、Ralf Steinbock、Alexej Scheremetjew、Rositha Kuniyil、Lars H. Finger、Antonis M. Messinis、Lutz Ackermann

  DOI：10.1002/anie.202000762

  日期：2020.6.26

  enabling the preparation of various bridgehead N‐fused [5,6]‐bicyclic heteroarenes through regioselective electrochemical C−H/N−H annulation without chemical metal oxidants. Novel azaruthenabicyclo[3.2.0]heptadienes were fully characterized and identified as key intermediates. Mechanistic studies are suggestive of an oxidatively induced reductive elimination pathway within a ruthenium(II/III) regime

  建立了咪唑与炔烃的钌催化电化学脱氢环化反应，无需化学金属氧化剂，即可通过区域选择性电化学CHH / NH环合制备各种桥头N-稠合[5,6]-双环杂芳烃。新型azaruthenabicyclocyclo [3.2.0]庚二烯已被充分表征并确定为关键中间体。机理研究表明钌（II / III）方案内的氧化诱导的还原消除途径。
• Catalyst-free one-pot synthesis of benzimidazoles from 1,2-diaminoarenes and alcohols
  作者：Mahender Reddy Marri、Swamy Peraka、Arun Kumar Macharla、Naresh Mameda、Srujana Kodumuri、Narender Nama

  DOI：10.1016/j.tetlet.2014.09.081

  日期：2014.11

  A new and efficient protocol is described for the one-pot synthesis of benzimidazoles from a variety of aryl alcohols and 1,2-diaminoarenes. The yields were ranging from moderate to excellent. Moreover, the present method is utilizing alcohols instead of aldehydes and the reactions are carried out under solvent- and catalyst-free conditions, offering an environmentally benign process.

  描述了一种新的有效方案，用于从多种芳基醇和1,2-二氨基芳烃一锅合成苯并咪唑。产量从中等到极好。而且，本方法利用醇代替醛，并且反应在无溶剂和无催化剂的条件下进行，提供了对环境无害的方法。
• Asymmetric hydroarylation of vinyl ethers catalyzed by a hydroxoiridium complex: azoles as effective directing groups
  作者：Daisuke Yamauchi、Takahiro Nishimura、Hideki Yorimitsu

  DOI：10.1039/c7cc00238f

  日期：——

  Asymmetric hydroarylation of vinyl ethers using azoles as directing groups was realized by use of a hydroxoiridium/chiral phosphine catalyst.

  通过使用羟基铱/手性膦催化剂，以唑类作为指导基团实现了乙烯基醚的不对称加氢反应。
• A one-step synthesis of substituted benzo- and pyridine-fused 1H-imidazoles
  作者：Sonu Kumar、Manash P. Sarmah、Yella Reddy、Ashish Bhatt、Ravi Kant

  DOI：10.1080/00397911.2021.2001658

  日期：2022.1.2

  Abstract Substituted benzimidazoles and pyrimidazoles are an important group of heterocyclic aromatic organic compounds in the field of medicinal chemistry. A one-step microwave accelerated synthesis of substituted benzo- and pyridine-fused 1H-imidazoles has been described. Mechanistically, the reaction proceeds by reacting substituted 2-fluoronitrobenzene and substituted arylamine through the formation

  摘要 取代的苯并咪唑类和嘧唑类化合物是药物化学领域中一类重要的杂环芳香族有机化合物。已经描述了取代苯并和吡啶稠合的 1H-咪唑的一步微波加速合成。从机理上讲，该反应通过取代的 2-氟硝基苯和取代的芳基胺通过形成 N-羟基中间体进行反应，该中间体在较高温度下裂解得到所需的产物。与先前描述的合成方法相比，这种方法实现了反应时间的减少、更高的产率、更清洁的反应。