N-(4-(1H-imidazol-1-yl)phenyl)acetamide | 83348-11-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(4-(1H-imidazol-1-yl)phenyl)acetamide
• 英文别名: 1-(4-acetamidophenyl)-1H-imidazole；N-[4-(1H-imidazol-1-yl)phenyl]acetamide；N-(4-imidazol-1-ylphenyl)acetamide
• CAS: 83348-11-2
• 化学式: C₁₁H₁₁N₃O
• mdl: MFCD08142660
• 分子量: 201.228
• InChiKey: SLCNHWPKGYFGIJ-UHFFFAOYSA-N

物化性质

• 熔点：
  164-166 °C
• 沸点：
  449.9±28.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  46.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  咪唑 、 N-(4-碘苯基)乙酰胺 在 copper(l) iodide 、 (2-guanidinyl)ethyl-cyclen 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以90%的产率得到N-(4-(1H-imidazol-1-yl)phenyl)acetamide
  参考文献：
  名称：

  周期数衍生物促进的杂环的N-芳基化

  摘要：

  已经研究了在中等温度下使用环素衍生物作为有效的有机碱和配体，有效地进行了铜催化的咪唑，吲哚和三唑与芳基或杂芳基卤化物的N芳基化反应。交叉耦合过程顺利进行，良品率极佳。

  DOI：

  10.1002/jhet.2188

文献信息

• CuI/L (L=pyridine-functionalized 1,3-diketones) catalyzed C–N coupling reactions of aryl halides with NH-containing heterocycles
  作者：Zhenxing Xi、Fenghui Liu、Yongbo Zhou、Wanzhi Chen

  DOI：10.1016/j.tet.2008.02.082

  日期：2008.5

  An efficient copper-catalyzed N-arylation and N-heteroarylation reactions of imidazole, pyrrole, indole, pyrazole, and perimidine with aryl or heteroaryl halides using pyridine-functionalized 1,3-diketone as ligands have been investigated. The ligands bearing pyridyl and 1,3-diketone moieties. which may form chelated Cu(I) species, are inexpensive and readily available. The combination of CuI and 1,3-di(pyridin-2-yl)propane- 1-3-dione is very efficient for C-N coupling reactions to afford various N-arylated products in good to excellent yields. (c) 2008 Elsevier Ltd. All rights reserved.
• 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.
• N-Arylation of Heterocycles Promoted by Cyclen Derivatives
  作者：Bao-Hua Zhang、Lan-xiang Shi、Si-Jie Liu、Rui-Xia Guo

  DOI：10.1002/jhet.2188

  日期：2015.7

  An efficient copper‐catalyzed N‐arylation reactions of imidazole, indole, and triazole with aryl or heteroaryl halides using cyclen derivatives as efficient organic base and ligand at moderate temperature have been investigated. The cross‐couplings proceed smoothly with good to excellent yields.

  已经研究了在中等温度下使用环素衍生物作为有效的有机碱和配体，有效地进行了铜催化的咪唑，吲哚和三唑与芳基或杂芳基卤化物的N芳基化反应。交叉耦合过程顺利进行，良品率极佳。