1,3-dimethyl-2-(2-methyl-imidazol-1-yl)-1H-indole | 1240039-17-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1,3-dimethyl-2-(2-methyl-imidazol-1-yl)-1H-indole
• 英文别名: 1,3-Dimethyl-2-(2-methylimidazol-1-yl)indole；1,3-dimethyl-2-(2-methylimidazol-1-yl)indole
• CAS: 1240039-17-1
• 化学式: C₁₄H₁₅N₃
• 分子量: 225.293
• InChiKey: XZRPGXQXZKXICJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  22.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-甲基咪唑 、 2-chloro-1,3-dimethyl-1H-indole 以 环丁砜 为溶剂， 反应 3.75h， 以68%的产率得到1,3-dimethyl-2-(2-methyl-imidazol-1-yl)-1H-indole
  参考文献：
  名称：

  Metal-Free Coupling of Azoles with 2- and 3-Haloindoles Providing Access to Novel 2- or 3-(Azol-1-yl)indole Derivatives

  摘要：

  Thermal or microwave-mediated heating of 2- or 3-haloindoles with azoles (pK(a) < 8) provides a straightforward, metal-free, and environmentally friendly access to novel 2-(azol-1-yl)indoles. Furthermore, previously unknown 2,3-bis(azolyl-1-yl)indoles can be prepared from 2,3-dihaloindoles by sequential reaction with two distinct azoles. This operationally simple acid-catalyzed process delivers novel indole derivatives in fair to excellent yields and expands the chemical diversity of substitutions that can be introduced on this medicinally important scaffold.

  DOI：

  10.1021/ol100685p

文献信息

• Metal-Free Coupling of Azoles with 2- and 3-Haloindoles Providing Access to Novel 2- or 3-(Azol-1-yl)indole Derivatives
  作者：Martin Poirier、Sébastien Goudreau、Jason Poulin、Jolaine Savoie、Pierre L. Beaulieu

  DOI：10.1021/ol100685p

  日期：2010.5.21

  Thermal or microwave-mediated heating of 2- or 3-haloindoles with azoles (pK(a) < 8) provides a straightforward, metal-free, and environmentally friendly access to novel 2-(azol-1-yl)indoles. Furthermore, previously unknown 2,3-bis(azolyl-1-yl)indoles can be prepared from 2,3-dihaloindoles by sequential reaction with two distinct azoles. This operationally simple acid-catalyzed process delivers novel indole derivatives in fair to excellent yields and expands the chemical diversity of substitutions that can be introduced on this medicinally important scaffold.