N-(tert-butyl)-6-(3,5-dimethoxyphenyl)-2-phenylimidazo[1,2-a]pyrazin-3-amine | 1395408-10-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(tert-butyl)-6-(3,5-dimethoxyphenyl)-2-phenylimidazo[1,2-a]pyrazin-3-amine
• 英文别名: N-tert-butyl-6-(3,5-dimethoxyphenyl)-2-phenylimidazo[1,2-a]pyrazin-3-amine
• CAS: 1395408-10-2
• 化学式: C₂₄H₂₆N₄O₂
• 分子量: 402.496
• InChiKey: LDKREJLRLDETER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  60.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-溴-3,5-二甲氧基苯 、 N-(tert-butyl)-2-phenylimidazo[1,2-a]pyrazin-3-amine 在 palladium diacetate 、 potassium carbonate 、 三苯基膦 、 三甲基乙酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以46%的产率得到N-(tert-butyl)-6-(3,5-dimethoxyphenyl)-2-phenylimidazo[1,2-a]pyrazin-3-amine
  参考文献：
  名称：

  C–H Bond Functionalization Under Metalation–Deprotonation Process: Regioselective Direct Arylation of 3-Aminoimidazo[1,2-a]pyrazine

  摘要：

  Concerted metalation deprotonation (CMD) approach with appropriate proton shuttle precursor, base, and solvent (PivOH-K2CO3-toluene) has rendered a regioselective Pd-catalyzed C6-arylation of 3-aminoimidazo[1,2-a]pyrazine, a therapeutically relevant scaffold accessible by multicomponent reaction. The arylation of this heteroarene suffers from competing C5 and C2'-arylation reactions, while the developed process has virtually eliminated these competing arylations. Density functional calculations for CMD C-H activation at C6, C5, C8, and C2' sites imply that the energy barrier with distortion energy penalty as major contributing component influences the regioselectivity.

  DOI：

  10.1021/jo301065s

文献信息

• C–H Bond Functionalization Under Metalation–Deprotonation Process: Regioselective Direct Arylation of 3-Aminoimidazo[1,2-<i>a</i>]pyrazine
  作者：Sankar K. Guchhait、Somnath Kandekar、Maneesh Kashyap、Nikhil Taxak、Prasad V. Bharatam

  DOI：10.1021/jo301065s

  日期：2012.9.21

  Concerted metalation deprotonation (CMD) approach with appropriate proton shuttle precursor, base, and solvent (PivOH-K2CO3-toluene) has rendered a regioselective Pd-catalyzed C6-arylation of 3-aminoimidazo[1,2-a]pyrazine, a therapeutically relevant scaffold accessible by multicomponent reaction. The arylation of this heteroarene suffers from competing C5 and C2'-arylation reactions, while the developed process has virtually eliminated these competing arylations. Density functional calculations for CMD C-H activation at C6, C5, C8, and C2' sites imply that the energy barrier with distortion energy penalty as major contributing component influences the regioselectivity.