N-benzyl-2-(4-cyanophenyl)-2-oxo-N-tosylacetamide | 1610846-89-3

• 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: N-benzyl-2-(4-cyanophenyl)-2-oxo-N-tosylacetamide
• 英文别名: N-benzyl-2-(4-cyanophenyl)-N-(4-methylphenyl)sulfonyl-2-oxoacetamide
• CAS: 1610846-89-3
• 化学式: C₂₃H₁₈N₂O₄S
• 分子量: 418.473
• InChiKey: YCFITCQYEBNSAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(2-(N-benzyl-N-tosylamino)ethynyl)benzonitrile 在 N-碘代丁二酰亚胺 、 二甲基亚砜 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以65%的产率得到N-benzyl-2-(4-cyanophenyl)-2-oxo-N-tosylacetamide
  参考文献：
  名称：

  Transition metal-free oxidation of ynamides for synthesis of α-keto-imides

  摘要：

  Transition metal-free double oxidation of triple bonds in ynamides for synthesis of alpha-keto-imides is described. The successful key was combination of NIS and DMSO under atmospheric air in CPME solvent, and the reaction quickly proceeds at 0 degrees C within 1 h. Although the yields and substrate generality are moderate, yet the prototype protocol avoids the use of expensive, moisture-sensitive, toxic, and explosive additives, which make it potentially and significantly greener than current alternatives. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.080

文献信息

• Transition metal-free oxidation of ynamides for synthesis of α-keto-imides
  作者：Takuya Chikugo、Yuta Yauchi、Masataka Ide、Tetsuo Iwasawa

  DOI：10.1016/j.tet.2014.04.080

  日期：2014.7

  Transition metal-free double oxidation of triple bonds in ynamides for synthesis of alpha-keto-imides is described. The successful key was combination of NIS and DMSO under atmospheric air in CPME solvent, and the reaction quickly proceeds at 0 degrees C within 1 h. Although the yields and substrate generality are moderate, yet the prototype protocol avoids the use of expensive, moisture-sensitive, toxic, and explosive additives, which make it potentially and significantly greener than current alternatives. (C) 2014 Elsevier Ltd. All rights reserved.