N-(3-(2-chlorophenyl)prop-2-ynyl)-4-nitrobenzenesulfonamide

• 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-(3-(2-chlorophenyl)prop-2-ynyl)-4-nitrobenzenesulfonamide
• 英文别名: N-(3-(2-chlorophenyl)prop-2-yn-1-yl)-4-nitrobenzenesulfonamide；N-[3-(2-chlorophenyl)prop-2-ynyl]-4-nitrobenzenesulfonamide
• 化学式: C₁₅H₁₁ClN₂O₄S
• 分子量: 350.782
• InChiKey: ZZUDYAGOAAQBCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(3-(2-chlorophenyl)prop-2-ynyl)-4-nitrobenzenesulfonamide 、 苯硼酸 在 [Rh(OH)(cod)]2 、 palladium diacetate 、 potassium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 16.0h， 以36%的产率得到1-(4-nitrophenylsulfonyl)-3-phenyl-1,2-dihydroquinoline
  参考文献：
  名称：

  Metal–Ligand Binding Interactions in Rhodium/Palladium-Catalyzed Synthesis of Dihydroquinolines

  摘要：

  A domino Rh- and Pd-catalyzed synthesis of dihydroquinolines is disclosed. Two metals and two ligands are placed in one reaction vessel along with the two reactive reagents to afford selective sequential coupling despite the potential for side reactions. In this report, we describe mechanistic investigations attempting to discern the catalystligand interactions occurring in this domino reaction. Through these studies, the reactivity and relative catalyst ligand loadings were successfully tuned to efficiently access the heterocyclic products.

  DOI：

  10.1021/jo502074s
• 作为产物：
  描述：

  tert-butyl 3-(2-chlorophenyl)prop-2-ynylcarbamate 在 盐酸 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 生成 N-(3-(2-chlorophenyl)prop-2-ynyl)-4-nitrobenzenesulfonamide
  参考文献：
  名称：

  Metal–Ligand Binding Interactions in Rhodium/Palladium-Catalyzed Synthesis of Dihydroquinolines

  摘要：

  A domino Rh- and Pd-catalyzed synthesis of dihydroquinolines is disclosed. Two metals and two ligands are placed in one reaction vessel along with the two reactive reagents to afford selective sequential coupling despite the potential for side reactions. In this report, we describe mechanistic investigations attempting to discern the catalystligand interactions occurring in this domino reaction. Through these studies, the reactivity and relative catalyst ligand loadings were successfully tuned to efficiently access the heterocyclic products.

  DOI：

  10.1021/jo502074s