2-(4-chlorophenyl)-4-phenyl-imidazole | 100558-20-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-chlorophenyl)-4-phenyl-imidazole
• 英文别名: 2-(4-chlorophenyl)-4(5)-phenylimidazole；2-(4-chlorophenyl)-4-phenyl-1H-imidazole；2-(4-chlorophenyl)-5-phenyl-1H-imidazole
• CAS: 100558-20-1
• 化学式: C₁₅H₁₁ClN₂
• 分子量: 254.719
• InChiKey: RYAFXUYSBDAZBC-UHFFFAOYSA-N

物化性质

• 熔点：
  263-265 °C (decomp)(Solv: ethanol (64-17-5); ethyl ether (60-29-7))
• 沸点：
  481.8±28.0 °C(Predicted)
• 密度：
  1.251±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  2
• 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-(4-chlorophenyl)-4-phenyl-imidazole 在 盐酸 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 C₁₅H₁₁ClN₂*(x)ClH
  参考文献：
  名称：

  Anticonvulsant activity of 2,4(1H)-diarylimidazoles in mice and rats acute seizure models

  摘要：

  2,4(1H)-Diarylimidazoles have been previously shown to inhibit hNaV1.2 sodium (Na) channel currents. Since many of the clinically used anticonvulsants are known to inhibit Na channels as an important mechanism of their action, these compounds were tested in two acute rodent seizure models for anticonvulsant activity (MES and scMet) and for sedative and ataxic side effects. Compounds exhibiting antiepileptic activity were further tested to establish a dose response curve (ED(50)). The experimental data identified four compounds with anticonvulsant activity in the MES acute seizure rodent model (compound 10, ED(50) = 61.7 mg/kg; compound 13, ED(50) = 46.8 mg/kg, compound 17, ED(50) = 129.5 mg/kg and compound 20, ED(50) = 136.7 mg/kg). Protective indexes (PI = TD(50)/ED(50)) ranged from 2.1 (compound 10) to greater than 3.6 (compounds 13, 17 and 20). All four compounds were shown to inhibit hNaV1.2 in a dose dependant manner. Even if a correlation between sodium channel inhibition and anticonvulsant activity was unclear, these studies identify four Na channel antagonists with anticonvulsant activity, providing evidence that these derivatives could be potential drug candidates for development as safe, new and effective antiepileptic drugs (AEDs). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.029
• 作为产物：
  描述：

  4-chloro-N-(2-oxo-2-phenylethyl)benzamide 在 ammonium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以75%的产率得到2-(4-chlorophenyl)-4-phenyl-imidazole
  参考文献：
  名称：

  Syntheses of 2-aryl-4-(3-thienyl)imidazole derivatives with antiinflammatory properties.

  摘要：

  研究人员合成了一系列 2-取代的 4-(3-噻吩基)咪唑（6、11 和 14），并对其抗炎活性进行了评估。其中，6g、14a 和 14g 具有很强的活性，与布洛芬的活性相当。与标准酸性消炎药相比，它们的急性毒性和致溃疡性较低。本文讨论了结构-活性关系。

  DOI：

  10.1248/cpb.34.3111

文献信息

• Modular Synthesis of Di- and Trisubstituted Imidazoles from Ketones and Aldehydes: A Route to Kinase Inhibitors
  作者：Ian de Toledo、Thiago A. Grigolo、James M. Bennett、Jonathan M. Elkins、Ronaldo A. Pilli

  DOI：10.1021/acs.joc.9b01844

  日期：2019.11.1

  A one-pot and modular approach to the synthesis of 2,4(5)-disubstituted imidazoles was developed based on ketone oxidation, employing catalytic HBr and DMSO, followed by imidazole condensation with aldehydes. This methodology afforded twenty-nine disubstituted NH-imidazoles (23%-85% yield). A three-step synthesis of 20 kinase inhibitors was achieved by employing this oxidation-condensation protocol

  基于酮氧化，采用催化HBr和DMSO，然后通过咪唑与醛的缩合反应，开发了一种单罐模块化方法，用于合成2,4（5）-二取代的咪唑。该方法提供了二十九个二取代的NH-咪唑（23％-85％的产率）。通过采用这种氧化-缩合方案，然后在咪唑环中进行溴化和Suzuki偶联，得到三取代的NH-咪唑（23％-69％，三步法），实现了三步合成20种激酶抑制剂的过程。该方法还用于合成已知抑制剂GSK3037619A。
• Nickel‐Catalyzed Construction of 2,4‐Disubstituted Imidazoles <i>via</i> C–C Coupling and C−N Condensation Cascade Reactions
  作者：Shengyang Fang、Haihua Yu、Xicheng Yang、Jianqi Li、Liming Shao

  DOI：10.1002/adsc.201900096

  日期：2019.7.11

  A convenient Ni(II)‐catalyzed C−C and C−N cascade coupling reaction was developed to directly access various 2,4‐disubstituted imidazoles. The reaction scope covers a variety of aryl and aliphatic substitutions, which demonstrate moderate‐to‐excellent yields. The tolerance of halogen and N‐containing heterocyclic groups demonstrates the versatility of this method for further synthetic explorations

  开发了一种方便的Ni（II）催化的C-C和C-N级联偶联反应，可直接使用各种2,4-二取代的咪唑。反应范围涵盖了各种芳基和脂肪族取代基，显示出中等至优异的收率。卤素和公差Ñ含杂环基团的演示此方法作进一步的合成探索的多功能性。
• Novel imidazole compound and use thereof
  申请人：Murai Takayuki

  公开号：US20070113930A1

  公开（公告）日：2007-05-24

  A water-based composition for treating copper or copper alloy surface for lead-free soldering, the composition comprising a compound represented by general formula (1): wherein R 1 is hydrogen or methyl, and either R 2 and R 3 represent chlorine and R 4 and R 5 represent hydrogen, or R 2 and R 3 represent hydrogen and R 4 and R 5 represent chlorine.

  一种用于无铅焊接处理铜或铜合金表面的水基组合物，该组合物包括由通式（1）表示的化合物： 其中R1为氢或甲基，且R2和R3表示氯，R4和R5表示氢，或者R2和R3表示氢，R4和R5表示氯。
• NOVEL IMIDAZOLE COMPOUND AND USAGE THEREOF
  申请人：SHIKOKU CHEMICALS CORPORATION

  公开号：EP1605078A1

  公开（公告）日：2005-12-14

  A water-based composition for treating copper or copper alloy surface for lead-free soldering, the composition comprising a compound represented by general formula (1): wherein R1 is hydrogen or methyl, and either R2 and R3 represent chlorine and R4 and R5 represent hydrogen, or R2 and R3 represent hydrogen and R4 and R5 represent chlorine.

  一种用于处理无铅焊接用铜或铜合金表面的水基组合物，该组合物包含通式 (1) 所代表的化合物： 其中 R1 是氢或甲基，R2 和 R3 代表氯，R4 和 R5 代表氢，或 R2 和 R3 代表氢，R4 和 R5 代表氯。
• SOLDERING PROCESS USING IMIDAZOLE COMPOUND
  申请人：SHIKOKU CHEMICALS CORPORATION

  公开号：EP1605078B1

  公开（公告）日：2010-07-21