2-(2-methyl-4-phenylthiazol-5-yl)benzonitrile | 1516952-46-7

• 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-(2-methyl-4-phenylthiazol-5-yl)benzonitrile
• 英文别名: 2-(2-Methyl-4-phenyl-1,3-thiazol-5-yl)benzonitrile；2-(2-methyl-4-phenyl-1,3-thiazol-5-yl)benzonitrile
• CAS: 1516952-46-7
• 化学式: C₁₇H₁₂N₂S
• 分子量: 276.362
• InChiKey: JCOLPXKPCZTFRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  64.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-溴甲基苯 、 2-(2-methyl-4-phenylthiazol-5-yl)benzonitrile 在 N-甲基吡咯烷酮 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 potassium acetate 作用下， 反应 16.0h， 以73%的产率得到2‐(2‐methyl‐4‐(3′‐methyl‐[1,1′‐biphenyl]‐2‐yl)thiazol‐5‐yl)benzonitrile
  参考文献：
  名称：

  4-苯基噻唑在钌催化的直接芳基化反应中的反应性

  摘要：

  研究了4-苯基噻唑的苯基取代基在Ru催化的直接芳基化反应中的反应性。发现4-苯基噻唑没有反应性。然而，在4-苯基噻唑的C5位引入芳基单元可增强其反应性，从而可以使用5 mol％的[Ru（p- cymene）以中等至高收率选择性地将4-苯基噻唑的苯基单元单芳基化）Cl 2 ] 2与KOPiv关联的催化剂前体。这些结果表明，4-苯基噻唑的构象和电子性质对于在催化循环过程中形成合适的中间体至关重要。该反应可同时耐受富电子和贫电子的芳基溴化物，从而可以直接调节芳基化的2-甲基-4-4-苯基-5-芳基噻唑的电子性质。

  DOI：

  10.1002/aoc.4794
• 作为产物：
  描述：

  2-溴苯乙酮 在 palladium diacetate 、 potassium carbonate 作用下， 以 N-甲基吡咯烷酮 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 生成 2-(2-methyl-4-phenylthiazol-5-yl)benzonitrile
  参考文献：
  名称：

  Synthesis of trisubstituted thiazoles by ligand-free palladium-catalyzed direct 5-arylation of 2,4-disubstituted thiazoles under conventional and microwave-assisted heating

  摘要：

  Trisubstituted thiazoles were synthesized with excellent yields using ligand-free, palladium-catalyzed, direct 5-arylation of 2,4-disubstituted thiazole and conventional or microwave-assisted heating. The palladium-catalyzed reaction yields were significantly influenced by LiCI additive, solvent, and heating method. The reaction times were reduced dramatically by employing microwave radiation instead of conventional heating. The synthetic methods can be applied to diverse 2,4,5-trisubstituted thiazoles by varying the aryl bromide and disubstituted thiazole reactants. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.10.053

文献信息

• Synthesis of trisubstituted thiazoles by ligand-free palladium-catalyzed direct 5-arylation of 2,4-disubstituted thiazoles under conventional and microwave-assisted heating
  作者：Su Kang Kim、Ji-Hyun Kim、Young Chul Park、Jae Won Kim、Eul Kgun Yum

  DOI：10.1016/j.tet.2013.10.053

  日期：2013.12

  Trisubstituted thiazoles were synthesized with excellent yields using ligand-free, palladium-catalyzed, direct 5-arylation of 2,4-disubstituted thiazole and conventional or microwave-assisted heating. The palladium-catalyzed reaction yields were significantly influenced by LiCI additive, solvent, and heating method. The reaction times were reduced dramatically by employing microwave radiation instead of conventional heating. The synthetic methods can be applied to diverse 2,4,5-trisubstituted thiazoles by varying the aryl bromide and disubstituted thiazole reactants. (C) 2013 Elsevier Ltd. All rights reserved.
• Reactivity of 4-phenylthiazoles in ruthenium catalyzed direct arylations
  作者：Ahmad Daher、Denis Jacquemin、Véronique Guerchais、Jean-François Soulé、Henri Doucet

  DOI：10.1002/aoc.4794

  日期：2019.4

  The reactivity of the phenyl substituent of 4‐phenylthiazoles in Ru‐catalyzed direct arylation was studied. 4‐Phenylthiazole was found to be unreactive; whereas, the introduction of an aryl unit at C5‐position of 4‐phenylthiazole enhances its reactivity, allowing the selective mono‐arylation of the phenyl unit of 4‐phenylthiazoles in moderate to high yields using 5 mol% of [Ru(p‐cymene)Cl2]2 catalyst

  研究了4-苯基噻唑的苯基取代基在Ru催化的直接芳基化反应中的反应性。发现4-苯基噻唑没有反应性。然而，在4-苯基噻唑的C5位引入芳基单元可增强其反应性，从而可以使用5 mol％的[Ru（p- cymene）以中等至高收率选择性地将4-苯基噻唑的苯基单元单芳基化）Cl 2 ] 2与KOPiv关联的催化剂前体。这些结果表明，4-苯基噻唑的构象和电子性质对于在催化循环过程中形成合适的中间体至关重要。该反应可同时耐受富电子和贫电子的芳基溴化物，从而可以直接调节芳基化的2-甲基-4-4-苯基-5-芳基噻唑的电子性质。