N-cyclohexene-1-carbonyl-3-methylindole | 1400666-14-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-cyclohexene-1-carbonyl-3-methylindole
• 英文别名: Cyclohexen-1-yl-(3-methylindol-1-yl)methanone；cyclohexen-1-yl-(3-methylindol-1-yl)methanone
• CAS: 1400666-14-9
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: WLCFZQOVJIQPNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-cyclohexene-1-carbonyl-3-methylindole 在 烟酸甲酯 、 氧气 、 palladium diacetate 、 三甲基乙酸 作用下， 以 均三甲苯 为溶剂， 反应 22.0h， 以71%的产率得到1-benzoyl-3-methylindole
  参考文献：
  名称：

  Aerobic Palladium(II)-Catalyzed Dehydrogenation of Cyclohexene-1-carbonyl Indole Amides: An Indole-Directed Aromatization

  摘要：

  A palladium(II)-catalyzed oxidative dehydrogenation of cyclohexene-1-carbonyl indole amides yielding the corresponding benzoylindoles is reported. The new aromatization is also applied to functionalized indoles such as tryptamine and tryptophan. The tethered indole is likely acting as a directing group for allylic C-H bond activation, and there is evidence for a mechanism proceeding through 1,3-diene formation followed by aromatization.

  DOI：

  10.1021/jo301088f

文献信息

• Aerobic Palladium(II)-Catalyzed Dehydrogenation of Cyclohexene-1-carbonyl Indole Amides: An Indole-Directed Aromatization
  作者：Sandeep R. Kandukuri、Martin Oestreich

  DOI：10.1021/jo301088f

  日期：2012.10.5

  A palladium(II)-catalyzed oxidative dehydrogenation of cyclohexene-1-carbonyl indole amides yielding the corresponding benzoylindoles is reported. The new aromatization is also applied to functionalized indoles such as tryptamine and tryptophan. The tethered indole is likely acting as a directing group for allylic C-H bond activation, and there is evidence for a mechanism proceeding through 1,3-diene formation followed by aromatization.