N-benzyl-2-(phenethylamino)benzenesulfonamide | 1202206-80-1

• 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-(phenethylamino)benzenesulfonamide
• 英文别名: N-benzyl-2-(2-phenylethylamino)benzenesulfonamide
• CAS: 1202206-80-1
• 化学式: C₂₁H₂₂N₂O₂S
• 分子量: 366.484
• InChiKey: PRBFCVXKACQMGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  66.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyl-2-(phenethylamino)benzenesulfonamide 、 N,N'-羰基二咪唑 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以94%的产率得到2-Benzyl-1,1-dioxo-4-(2-phenylethyl)-1lambda6,2,4-benzothiadiazin-3-one
  参考文献：
  名称：

  Microwave-assisted sequential one-pot protocol to benzothiadiazin-3-one-1,1-dioxides via a copper-catalyzed N-arylation strategy

  摘要：

  A microwave-assisted, sequential, one-pot protocol has been developed for the synthesis of a variety of benzothiadiazin-3-one-1,1-dioxides. This protocol utilizes a copper-catalyzed N-arylation of alpha-bromo-benzenesulfonamides with a number of amines to generate the corresponding 2-aminobenzenesulfonamides, which undergo cyclization to the desired sultams using carbonyl diimidazole (M). A range of conditions was evaluated for the key C-N bond formation step with tolerance toward functionalized amines. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.090
• 作为产物：
  描述：

  2-苯乙胺 、 N-苄基-2-溴苯磺酰胺 在 copper(l) iodide 、 1,10-菲罗啉 、 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.18h， 以91%的产率得到N-benzyl-2-(phenethylamino)benzenesulfonamide
  参考文献：
  名称：

  Microwave-assisted sequential one-pot protocol to benzothiadiazin-3-one-1,1-dioxides via a copper-catalyzed N-arylation strategy

  摘要：

  A microwave-assisted, sequential, one-pot protocol has been developed for the synthesis of a variety of benzothiadiazin-3-one-1,1-dioxides. This protocol utilizes a copper-catalyzed N-arylation of alpha-bromo-benzenesulfonamides with a number of amines to generate the corresponding 2-aminobenzenesulfonamides, which undergo cyclization to the desired sultams using carbonyl diimidazole (M). A range of conditions was evaluated for the key C-N bond formation step with tolerance toward functionalized amines. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.090

文献信息

• Microwave-assisted sequential one-pot protocol to benzothiadiazin-3-one-1,1-dioxides via a copper-catalyzed N-arylation strategy
  作者：Alan Rolfe、Paul R. Hanson

  DOI：10.1016/j.tetlet.2009.09.090

  日期：2009.12

  A microwave-assisted, sequential, one-pot protocol has been developed for the synthesis of a variety of benzothiadiazin-3-one-1,1-dioxides. This protocol utilizes a copper-catalyzed N-arylation of alpha-bromo-benzenesulfonamides with a number of amines to generate the corresponding 2-aminobenzenesulfonamides, which undergo cyclization to the desired sultams using carbonyl diimidazole (M). A range of conditions was evaluated for the key C-N bond formation step with tolerance toward functionalized amines. (C) 2009 Elsevier Ltd. All rights reserved.