3-(4-(trifluoromethyl)phenyl)-2-phenylimidazo[1,2-a]pyrimidine | 909104-05-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-(trifluoromethyl)phenyl)-2-phenylimidazo[1,2-a]pyrimidine
• CAS: 909104-05-8
• 化学式: C₁₉H₁₂F₃N₃
• 分子量: 339.32
• InChiKey: AYIKJHGUKAMHBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.08
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  30.19
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(4-(trifluoromethyl)phenyl)-2-phenylimidazo[1,2-a]pyrimidine 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以88%的产率得到4-phenyl-5-(4-(trifluoromethyl)phenyl)-1H-imidazol-2-amine
  参考文献：
  名称：

  Microwave-assisted synthesis of substituted 2-amino-1H-imidazoles from imidazo[1,2-a]pyrimidines

  摘要：

  An efficient method for the synthesis of mono- and disubstituted 2-amino-1H-imidazoles via microwave-assisted hydrazinolysis of substituted imidazo[1,2-a]pyrimidines is reported. This protocol avoids strong acidic conditions and is superior to the classical cyclocondensation of alpha-haloketones with N-acetylguanidine. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.128
• 作为产物：
  描述：

  1,3,5-三嗪-2,4,6-三胺,N,N'''-1,2-乙二基二[N-[3-[[4,6-二[丁基(2,2,6,6-四甲基-4-哌啶基)氨基]-1,3,5-三嗪-2-基]氨基]丙基]-N,N''-二丁基-N,N''-二(2,2,6,6-四甲基-4-哌啶基)- 、 2-Bromo-1-phenyl-2-[4-(trifluoromethyl)phenyl]ethanone 以 乙腈 为溶剂， 生成 3-(4-(trifluoromethyl)phenyl)-2-phenylimidazo[1,2-a]pyrimidine
  参考文献：
  名称：

  Structure−Activity Relationship of 4(5)-Aryl-2-amino-1H-imidazoles, N1-Substituted 2-Aminoimidazoles and Imidazo[1,2-a]pyrimidinium Salts as Inhibitors of Biofilm Formation by Salmonella Typhimurium and Pseudomonas aeruginosa

  摘要：

  A library of 112 4(5)-aryl-2-amino-1H-imidazoles, 4,5-diphenyl-2-amino-1H-imidazoles, and N1-substituted 4(5)-phenyl-2-aminoimidazoles was synthesized and tested for the antagonistic effect against biofilm formation by Salmonella Typhimurium and Pseudomonas aeruginosa. The substitution pattern of the 4(5)phenyl group and the nature of the N1-substituent were found to have a major effect on the biofilm inhibitory activity. The most active compounds of this series were shown to inhibit the biofilm formation at low micromolar concentrations. Furthermore, the influence of 6 imidazo[1,2-a]pyrimidines and 18 imidazo[1,2-a]pyrimidinium salts on the biofilm formation was tested. These compounds are the chemical precursors of the 2-aminoimidazoles in our synthesis pathway. A good correlation was found between the activity of the imidazo[1,2-a]pyrimidinium salts and their corresponding 2-aminoimidazoles, supporting the hypothesis that the imidazo[1,2-a]pyrimidinium salts are possibly cleaved by cellular nucleophiles to form the active 2-aminoimidazoles. However, the imidazo[1,2-a]pyrimidines did not show any biofilm inhibitory activity, indicating that these molecules are not susceptible to in situ degradation to 2-aminoimidazoles. Finally, we demonstrated the lack of biofilm inhibitory activity of an array of 37 2N-substituted 2-aminopyrimidines, which are the chemical precursors of the imidazo[1,2-a]pyrimidinium salts in our synthesis pathway.

  DOI：

  10.1021/jm1011148

文献信息

• Predictable and Site-Selective Functionalization of Poly(hetero)arene Compounds by Palladium Catalysis
  作者：David Lapointe、Thomas Markiewicz、Christopher J. Whipp、Amy Toderian、Keith Fagnou

  DOI：10.1021/jo102081a

  日期：2011.2.4

  addressed by two different approaches. Site-selectivity can be obtained by applying various reaction conditions that are (hetero)arene specific to substrates that contain indoles, pyridine N-oxide, and polyfluorinated benzenes. An experimental classification of electron-rich heteroarenes based on their reactivity toward palladium-catalyzed C−H functionalization was established, the result of which correlated

  通过两种不同的方法解决了在复杂的聚（杂）芳族底物的CH键处实现选择性和可预测的官能化的挑战。可以通过对包含吲哚，吡啶N的底物应用各种（杂）芳烃特异的反应条件来获得位点选择性氧化物和多氟苯。建立了基于富电子杂芳基对钯催化的CH官能化的反应性的实验分类，其结果与DFT计算的协同金属化-去质子化（CMD）途径预测的反应性顺序密切相关。然后，在常规反应条件下，将包含两个反应性杂芳基的模型底物进行反应，以证明该反应性图可用于预测钯催化的直接芳基化和苄基化反应的区域选择性。