2-bromo-3-phenylimidazo[1,2-a]pyrimidine | 1391625-08-3

• 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-bromo-3-phenylimidazo[1,2-a]pyrimidine
• CAS: 1391625-08-3
• 化学式: C₁₂H₈BrN₃
• 分子量: 274.12
• InChiKey: LNCNTTOHBMRZIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.19
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  苯乙炔 在 N-溴代丁二酰亚胺(NBS) 、 氧气 、 copper(II) bis(trifluoromethanesulfonate) 、 silver nitrate 作用下， 以 丙酮 、 乙腈 为溶剂， 20.0~60.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 生成 2-bromo-3-phenylimidazo[1,2-a]pyrimidine
  参考文献：
  名称：

  铜催化卤代炔烃的分子间氧化环化：2-卤代取代的咪唑并[1,2- a ]吡啶，咪唑并[1,2- a ]吡嗪和咪唑并[1,2- a ]嘧啶的合成

  摘要：

  AbstractAn efficient copper‐catalyzed method for the synthesis of 2‐haloimidazopyridines with aminopyridines and haloalkynes using molecular oxygen as oxidant in a one‐pot manner has been developed. In this process, the reaction appears to be very general and suitable for the construction of a variety of 2‐halo‐substituted imidazopyridines, imidazopyrazines and imidazopyrimidines. The intermolecular oxidative diamination of haloalkynes was achieved for the first time. Importantly, the mild reaction conditions and the efficient conversion of the alkyl‐substituted haloalkynes are great improvements over the existing methods. Moreover, the resultant 2‐haloimidazo[1,2‐a]pyridines could be efficiently converted to other functionalized imidazopyridine products via substitution, coupling reactions and other transformations, which further indicates potential applications of this method in synthetic and pharmaceutical chemistry.magnified image

  DOI：

  10.1002/adsc.201300157