2-(1H-imidazol-1-yl)-1,3-dimethyl-1H-indole | 1225068-02-9

• 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: 2-(1H-imidazol-1-yl)-1,3-dimethyl-1H-indole
• 英文别名: 2-imidazol-1-yl-1,3-dimethyl-1H-indole；2-Imidazol-1-yl-1,3-dimethylindole；2-imidazol-1-yl-1,3-dimethylindole
• CAS: 1225068-02-9
• 化学式: C₁₃H₁₃N₃
• 分子量: 211.266
• InChiKey: DZGMNMHGUQTYJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：

  咪唑 、 2-chloro-1,3-dimethyl-1H-indole 以 环丁砜 为溶剂， 反应 0.67h， 以71%的产率得到2-(1H-imidazol-1-yl)-1,3-dimethyl-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

• NaClO‐Mediated Cross Installation of Indoles and Azoles Benefits Anticancer Hit Discovery
  作者：Changjun Yu、Ruiyao E.、Xiao‐Wei Zhang、Wen‐Qian Hu、Guangjun Bao、Yiping Li、Yuyang Liu、Zeyuan He、Jingyue Li、Wen Ma、Ling‐Yun Mou、Rui Wang、Wangsheng Sun

  DOI：10.1002/cmdc.202200651

  日期：2023.3

  A rapid, effective NaClO-mediated cross installation of indoles and azoles for the construction of various N-linked 2-(azol-1-yl) indole derivatives and the late-stage functional modification of drugs and peptides has been developed, which can benefit anticancer hit discovery.

  开发了一种快速、有效的NaClO 介导的吲哚和唑的交叉安装，用于构建各种 N-连接的 2-(azol-1-yl) 吲哚衍生物以及药物和多肽的后期功能修饰，这可以受益抗癌发现。