(E)-2-(4-chlorostyryl)-6-methylimidazo[1,2-a]pyridine | 1505454-44-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: (E)-2-(4-chlorostyryl)-6-methylimidazo[1,2-a]pyridine
• 英文别名: 2-[(E)-2-(4-chlorophenyl)ethenyl]-6-methylimidazo[1,2-a]pyridine
• CAS: 1505454-44-3
• 化学式: C₁₆H₁₃ClN₂
• 分子量: 268.746
• InChiKey: VRERBXMMSUWAHH-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 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：
  17.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-氨基-5-甲基吡啶 、 (3E)-4-(4-chlorophenyl)-3-buten-2-one 在 indium(III) triflate 、 copper(l) iodide 、 氧气 作用下， 以 N-甲基吡咯烷酮 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 30.0h， 以77%的产率得到(E)-2-(4-chlorostyryl)-6-methylimidazo[1,2-a]pyridine
  参考文献：
  名称：

  CuI-Catalyzed Aerobic Oxidative α-Aminaton Cyclization of Ketones to Access Aryl or Alkenyl-Substituted Imidazoheterocycles

  摘要：

  CuI-catalyzed aerobic oxidative synthesis of imidazoheterocycles has been achieved. Four hydrogen atoms were removed in one step. This protocol was compatible with a broad range of functional groups, and it has been also successfully extended to unsaturated ketones, bringing about the formation of alkenyl-substituted imidazoheterocycles, which were difficult to prepare by previous means. Preliminary mechanistic studies indicated that this reaction was most likely to proceed through a catalytic Ortoleva-King reaction. By using this method, the marketed drug Zolimidine could be prepared with 90% yield on a gram scale from commercially available materials.

  DOI：

  10.1021/jo402134x

文献信息

• CuI-Catalyzed Aerobic Oxidative α-Aminaton Cyclization of Ketones to Access Aryl or Alkenyl-Substituted Imidazoheterocycles
  作者：Yuanfei Zhang、Zhengkai Chen、Wenliang Wu、Yuhong Zhang、Weiping Su

  DOI：10.1021/jo402134x

  日期：2013.12.20

  CuI-catalyzed aerobic oxidative synthesis of imidazoheterocycles has been achieved. Four hydrogen atoms were removed in one step. This protocol was compatible with a broad range of functional groups, and it has been also successfully extended to unsaturated ketones, bringing about the formation of alkenyl-substituted imidazoheterocycles, which were difficult to prepare by previous means. Preliminary mechanistic studies indicated that this reaction was most likely to proceed through a catalytic Ortoleva-King reaction. By using this method, the marketed drug Zolimidine could be prepared with 90% yield on a gram scale from commercially available materials.