3-oxo-N,2-diphenyl-2,3-dihydrobenzo[d][1,2]selenazole-7-carboxamide | 1256846-47-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-oxo-N,2-diphenyl-2,3-dihydrobenzo[d][1,2]selenazole-7-carboxamide
• 英文别名: 3-oxo-N,2-diphenyl-1,2-benzoselenazole-7-carboxamide
• CAS: 1256846-47-5
• 化学式: C₂₀H₁₄N₂O₂Se
• 分子量: 393.303
• InChiKey: XEOGQUYFDABZMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-bromo-N1,N3-diphenylisophthalamide 在 selenium 、 copper(l) iodide 、 1,10-菲罗啉 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以96%的产率得到3-oxo-N,2-diphenyl-2,3-dihydrobenzo[d][1,2]selenazole-7-carboxamide
  参考文献：
  名称：

  Cu-Catalyzed Efficient Synthetic Methodology for Ebselen and Related Se−N Heterocycles

  摘要：

  An efficient copper-catalyzed method for the synthesis of biologically important ebselen and related analogues containing a Se-N bond has been developed. This is the first report of a catalytic process of selenation and Se-N bond formation reaction. Copper-catalyzed reaction tolerates functional groups such as amides, hydroxyls, ethers, nitro, fluorides, and chlorides. The best results are obtained by using a combination of potassium carbonate as a base, Iodo- or bromo-arylamide substrates, selenium powder, and copper iodide catalyst.

  DOI：

  10.1021/ol102027j

文献信息

• Cu-Catalyzed Efficient Synthetic Methodology for Ebselen and Related Se−N Heterocycles
  作者：Shah Jaimin Balkrishna、Bhagat Singh Bhakuni、Deepak Chopra、Sangit Kumar

  DOI：10.1021/ol102027j

  日期：2010.12.3

  An efficient copper-catalyzed method for the synthesis of biologically important ebselen and related analogues containing a Se-N bond has been developed. This is the first report of a catalytic process of selenation and Se-N bond formation reaction. Copper-catalyzed reaction tolerates functional groups such as amides, hydroxyls, ethers, nitro, fluorides, and chlorides. The best results are obtained by using a combination of potassium carbonate as a base, Iodo- or bromo-arylamide substrates, selenium powder, and copper iodide catalyst.