1,3-dimethyl-2-pyrazol-1-yl-1H-indole | 1225068-00-7

• 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-pyrazol-1-yl-1H-indole
• 英文别名: 1,3-Dimethyl-2-pyrazol-1-ylindole；1,3-dimethyl-2-pyrazol-1-ylindole
• CAS: 1225068-00-7
• 化学式: C₁₃H₁₃N₃
• 分子量: 211.266
• InChiKey: LXEOMSNCLVITPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  吡唑 、 1,3-二甲基吲哚 在 碘 、 甲酸铵 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以93%的产率得到1,3-dimethyl-2-pyrazol-1-yl-1H-indole
  参考文献：
  名称：

  Highly Regioselective C–N Bond Formation through C–H Azolation of Indoles Promoted by Iodine in Aqueous Media

  摘要：

  An efficient and metal-free method for the direct C-N coupling of indoles with azoles to produce 2-(azol-1-yl)indoles in aqueous solution has been developed. This reaction proceeded highly regioselectively to provide a variety of indole derivatives with good to excellent yields.

  DOI：

  10.1021/ol302609m

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.