(E)-2-(2-(thiophen-2-yl)vinyl)imidazo[2,1-a]isoquinoline | 1505454-54-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (E)-2-(2-(thiophen-2-yl)vinyl)imidazo[2,1-a]isoquinoline
• 英文别名: 2-[(E)-2-thiophen-2-ylethenyl]imidazo[2,1-a]isoquinoline
• CAS: 1505454-54-5
• 化学式: C₁₇H₁₂N₂S
• 分子量: 276.362
• InChiKey: ZEZDOPZPZACQTA-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-氨基异喹啉 、 (E)-4-(2-thienyl)but-3-en-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73%的产率得到(E)-2-(2-(thiophen-2-yl)vinyl)imidazo[2,1-a]isoquinoline
  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.