2-(1H-Imidazol-1-yl)-4-methylbenzenamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(1H-Imidazol-1-yl)-4-methylbenzenamine
• 英文别名: 2-Imidazol-1-yl-4-methylaniline
• 化学式: C₁₀H₁₁N₃
• 分子量: 173.217
• InChiKey: OEXYMFAEBMYCIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1H-Imidazol-1-yl)-4-methylbenzenamine 在 potassium phosphate 、 copper(l) iodide 、 1,10-菲罗啉 、 氧气 、 copper diacetate 、 sodium acetate 作用下， 以 四氢呋喃 、 间二甲苯 为溶剂， 110.0~155.0 ℃ 、101.33 kPa 条件下， 反应 79.0h， 生成 9-(4-methylphenyl)-6-methylimidazo[1,2-a]benzimidazole
  参考文献：
  名称：

  Copper-Catalyzed Aerobic Oxidative Intramolecular C–H Amination Leading to Imidazobenzimidazole Derivatives

  摘要：

  A highly efficient copper-catalyzed aerobic oxidative intramolecular C-H amination has been developed using substituted 2-(1H-imidazol-1-yl)-N-alkylbenzenamines as the starting materials, and the corresponding imidazobenzimidazole derivatives were obtained in excellent yields. This is an economical and practical method for the construction of N-heterocycles.

  DOI：

  10.1021/ol202884z
• 作为产物：
  描述：

  3-氟-4-硝基甲苯 在 copper(l) iodide 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~110.0 ℃ 、303.99 kPa 条件下， 反应 28.0h， 生成 2-(1H-Imidazol-1-yl)-4-methylbenzenamine
  参考文献：
  名称：

  Copper-Catalyzed Aerobic Oxidative Intramolecular C–H Amination Leading to Imidazobenzimidazole Derivatives

  摘要：

  A highly efficient copper-catalyzed aerobic oxidative intramolecular C-H amination has been developed using substituted 2-(1H-imidazol-1-yl)-N-alkylbenzenamines as the starting materials, and the corresponding imidazobenzimidazole derivatives were obtained in excellent yields. This is an economical and practical method for the construction of N-heterocycles.

  DOI：

  10.1021/ol202884z

文献信息

• Scaffold Diversity through a Branching Double-Annulation Cascade Strategy: Iminium-Induced One-Pot Synthesis of Diverse Fused Tetrahydroisoquinoline Scaffolds
  作者：Duddu S. Sharada、Anand H. Shinde、Srilaxmi M. Patel、Shinde Vidyacharan

  DOI：10.1021/acs.joc.6b01096

  日期：2016.8.5

  double-annulation cascade (BDAC) strategy for diverse and complex fused THIQ scaffolds via a highly reactive iminium-induced one-pot double-cyclization sequence involving Pictect–Spengler-type cyclization has been developed for the first time. The salient features of this protocol are that it allows direct and rapid access to unprecedented diverse fused THIQ skeletons, is metal/catalyst free, has a

  首次开发了通过涉及Pictect-Spengler型环化反应的高反应性亚胺诱导的一锅双环化序列，对多样复杂的THIQ支架进行支化的双环级联（BDAC）策略。该协议的显着特点是，它可以直接，快速地访问前所未有的各种熔融THIQ骨架，不含金属/催化剂，反应曲线更干净，提供了良好的产率，是一种方便的方法。这种无催化剂的多米诺骨牌工艺通过在统一的反应条件下一步形成两个C–N和一个C–X（X = C，N，O）键，从而促进了多种脚手架构建剂的双重成环。此外，我们揭示了一个异常的双BDAC序列，导致N-N连接的异喹啉二聚体。
• US6235740B1
  申请人：——

  公开号：US6235740B1

  公开（公告）日：2001-05-22
• [EN] IMIDAZOQUINOXALINE PROTEIN TYROSINE KINASE INHIBITORS<br/>[FR] INHIBITEURS A BASE D'IMIDAZOQUINOXALINES DE LA PROTEINE TYROSINE KINASE
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：WO1999009845A1

  公开（公告）日：1999-03-04

  (EN) Novel imidazoquinoxalines and salts thereof, pharmaceutical compositions containing such compounds, and methods of using such compounds in the treatment of protein tyrosine kinase-associated disorders such as immunologic disorders.(FR) La présente invention concerne de nouvelles imidazoquinoxalines et des sels de celles-ci, des compositions pharmaceutiques contenant ces composés et des procédés d'utilisation de ces composés dans le traitement de troubles associés à la protéine tyrosine kinase, tels que des troubles immunologiques.
• Copper-Catalyzed Aerobic Oxidative Intramolecular C–H Amination Leading to Imidazobenzimidazole Derivatives
  作者：Xiaoqiang Wang、Yunhe Jin、Yufen Zhao、Lin Zhu、Hua Fu

  DOI：10.1021/ol202884z

  日期：2012.1.20

  A highly efficient copper-catalyzed aerobic oxidative intramolecular C-H amination has been developed using substituted 2-(1H-imidazol-1-yl)-N-alkylbenzenamines as the starting materials, and the corresponding imidazobenzimidazole derivatives were obtained in excellent yields. This is an economical and practical method for the construction of N-heterocycles.