5-Methyl-1-(4'-methoxyphenyl)imidazol | 21497-98-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-Methyl-1-(4'-methoxyphenyl)imidazol
• 英文别名: 1-(4-methoxyphenyl)-5-methylimidazole；1-(4-methoxy-phenyl)-5-methyl-1H-imidazole
• CAS: 21497-98-3
• 化学式: C₁₁H₁₂N₂O
• 分子量: 188.229
• InChiKey: XBLYQEJHPFWZNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-甲基咪唑 、 4-甲氧基苯硼酸 在 4,4'-bis[1H,1H,2H,2H,3H,3H-perfluorononyl]-2,2'-bipyridine 、 氧气 、 copper diacetate 作用下， 以 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 生成 5-Methyl-1-(4'-methoxyphenyl)imidazol 、 1-(4-甲氧基苯基)-4-甲基-1H-咪唑
  参考文献：
  名称：

  Efficient use of a surfactant for copper-catalyzed coupling reaction of arylboronic acids with imidazoles in water

  摘要：

  Copper-catalyzed oxidative coupling of arylboronic acids with imidazoles in water was realized by using an amphiphilic surfactant. By choosing an appropriate surfactant, reactions of a variety of arylboronic acids proceeded smoothly under mild and base-free conditions, providing an efficient, practical, and greener method for the synthesis of N-arylimidazoles. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.07.042

文献信息

• N-(1-Oxy-2-picolyl)oxalamic acids as a new type of O,O-ligands for the Cu-catalyzed N-arylation of azoles with aryl halides in water or organic solvent
  作者：Yongbin Wang、Yu Zhang、Beibei Yang、Ao Zhang、Qizheng Yao

  DOI：10.1039/c5ob00045a

  日期：——

  identified as novel efficient ligands for copper-catalyzed C–N cross-coupling of azoles and aryl halides in water. The N-arylation of imidazoles, indoles and pyrazoles proceeded with moderate to excellent yields and complete selectivity over aromatic amines and phenols. Moreover, L5, which is also efficient in organic solvent with low catalyst loading, can be used to promote the N-arylation reactions with

  N-（1-氧-吡啶-2-基甲基）草酰胺酸（L3-L5）被确定为铜催化水中C-N偶氮与芳基卤化物交叉偶联的新型有效配体。咪唑，吲哚和吡唑的N-芳基化反应具有中等至极好的收率，并且相对于芳族胺和酚具有完全的选择性。此外，在低催化剂负载量的有机溶剂中也有效的L5可用于促进与水敏材料的N-芳基化反应。根据一些验证实验的结果提出了催化机理，结果表明，作为新型螯合剂的配体可以与N的两个氧原子配位到Cu（I）-氧化物和酰胺在偶联过程中。
• Highly Functional Group Tolerance in Copper-Catalyzed <i>N</i>-Arylation of Nitrogen-Containing Heterocycles under Mild Conditions
  作者：Liangbo Zhu、Gaocan Li、Liang Luo、Peng Guo、Jingbo Lan、Jingsong You

  DOI：10.1021/jo802669b

  日期：2009.3.6

  A copper-catalyzed process has been developed for the N-arylation reaction under very mild conditions in the absence of additional ligand. This protocol could not only tolerate an array of thermally sensitive functional groups, but also achieve high chemoselectivity.
• Efficient use of a surfactant for copper-catalyzed coupling reaction of arylboronic acids with imidazoles in water
  作者：Kiyofumi Inamoto、Kanako Nozawa、Jun Kadokawa、Yoshinori Kondo

  DOI：10.1016/j.tet.2012.07.042

  日期：2012.9

  Copper-catalyzed oxidative coupling of arylboronic acids with imidazoles in water was realized by using an amphiphilic surfactant. By choosing an appropriate surfactant, reactions of a variety of arylboronic acids proceeded smoothly under mild and base-free conditions, providing an efficient, practical, and greener method for the synthesis of N-arylimidazoles. (C) 2012 Elsevier Ltd. All rights reserved.