1-[1-(toluene-4-sulfonyl)-1,4,5,6-tetrahydroindol-7-ylidene]pentan-2-one | 881189-59-9

• 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: 1-[1-(toluene-4-sulfonyl)-1,4,5,6-tetrahydroindol-7-ylidene]pentan-2-one
• 英文别名: (1E)-1-[1-(4-methylphenyl)sulfonyl-5,6-dihydro-4H-indol-7-ylidene]pentan-2-one
• CAS: 881189-59-9
• 化学式: C₂₀H₂₃NO₃S
• 分子量: 357.474
• InChiKey: IBAHGJZXIPMXPH-SAPNQHFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  64.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-9-[1-(Toluene-4-sulfonyl)-1H-pyrrol-3-yl]-non-5-en-4-one 在 氧气 、 palladium diacetate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 二甲基亚砜 为溶剂， 反应 48.0h， 以60%的产率得到1-[1-(toluene-4-sulfonyl)-1,4,5,6-tetrahydroindol-7-ylidene]pentan-2-one
  参考文献：
  名称：

  Mild Aerobic Oxidative Palladium (II) Catalyzed C−H Bond Functionalization:  Regioselective and Switchable C−H Alkenylation and Annulation of Pyrroles

  摘要：

  A palladium catalyzed C-H bond functionalization system that operates under ambient and aerobic conditions can be used to alkenylate pyrroles with control of regioselectivty. A steric and electronic control strategy can be used to influence positional control in the C-H bond functionalization process that results in either the C2 or C3 alkenylated products. Air, molecular oxygen, or tBuOOBz can be used as reoxidant in this mild process, and the reaction works on a range of substrates. Finally a catalytic aerobic annulation strategy is described that can be controlled to produce cyclization at either the C2 or C3 positions, thus forming diverse pyrrole products.

  DOI：

  10.1021/ja058141u

文献信息

• Mild Aerobic Oxidative Palladium (II) Catalyzed C−H Bond Functionalization:  Regioselective and Switchable C−H Alkenylation and Annulation of Pyrroles
  作者：Elizabeth M. Beck、Neil P. Grimster、Richard Hatley、Matthew J. Gaunt

  DOI：10.1021/ja058141u

  日期：2006.3.1

  A palladium catalyzed C-H bond functionalization system that operates under ambient and aerobic conditions can be used to alkenylate pyrroles with control of regioselectivty. A steric and electronic control strategy can be used to influence positional control in the C-H bond functionalization process that results in either the C2 or C3 alkenylated products. Air, molecular oxygen, or tBuOOBz can be used as reoxidant in this mild process, and the reaction works on a range of substrates. Finally a catalytic aerobic annulation strategy is described that can be controlled to produce cyclization at either the C2 or C3 positions, thus forming diverse pyrrole products.