4-(5-methyl-2-phenyl-1H-indol-3-yl)butan-2-one

• 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: 4-(5-methyl-2-phenyl-1H-indol-3-yl)butan-2-one
• 化学式: C₁₉H₁₉NO
• 分子量: 277.366
• InChiKey: PBBUAMFLDJRPPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-溴-4-甲基苯胺 在 bis-triphenylphosphine-palladium(II) chloride 哌啶 、 copper(l) iodide 、 sodium tetrachloroaurate(III) 作用下， 以 乙醇 为溶剂， 反应 52.5h， 生成 4-(5-methyl-2-phenyl-1H-indol-3-yl)butan-2-one
  参考文献：
  名称：

  Gold-Catalyzed Reactions of 2-Alkynyl-phenylamines with α,β-Enones

  摘要：

  The gold-catalyzed reaction of 2-alkynyl-phenylamines with alpha,beta-enones represents a new general one-pot entry into C-3-alkyl-indoles by sequential reactions. Gold-catalyzed sequential cyclization/alkylation, N-alkylation/cyclization, or N-alkylation/cyclization/alkylation reactions leading to different indoles can be directed by changing the 2-alkynyl-phenylamine 1/alpha,beta-enone 3 ratio and the reaction temperature. Unusual gold-catalyzed rearrangement reaction of indoles are observed at 140 degrees C. New gold-catalyzed formation of propargyl-alkyl ether under mild conditions and the hydration reaction of N-acetyl-2-ethynyl-phenylamine are reported.

  DOI：

  10.1021/jo047793i

文献信息

• Nucleopalladation Triggering the Oxidative Heck Reaction: A General Strategy to Diverse β-Indole Ketones
  作者：Qian Wang、Liangbin Huang、Xia Wu、Huanfeng Jiang

  DOI：10.1021/ol4027683

  日期：2013.12.6

  A simple and efficient palladium-catalyzed oxidative coupling between 2-alkynyl anilines and allylic alcohols is described by using cheap and green dioxygen as the oxidant. These cross-couplings have a large functional group tolerance and are of higher reactivity toward electron nonbaised allylic alcohols. The resultant β-indole ketones are readily converted to pharmaceutically significant β-indole

  通过使用廉价的绿色双氧作为氧化剂，描述了2-炔基苯胺和烯丙基醇之间简单而有效的钯催化的氧化偶合。这些交叉偶联具有大的官能团耐受性，并且对电子非卤代烯丙基醇具有更高的反应性。所得的β-吲哚酮易于转化为具有药学意义的β-吲哚醇/胺和吡咯并[2,1- a ]异喹啉。
• Gold-Catalyzed Reactions of 2-Alkynyl-phenylamines with α,β-Enones
  作者：Maria Alfonsi、Antonio Arcadi、Massimiliano Aschi、Gabriele Bianchi、Fabio Marinelli

  DOI：10.1021/jo047793i

  日期：2005.3.1

  The gold-catalyzed reaction of 2-alkynyl-phenylamines with alpha,beta-enones represents a new general one-pot entry into C-3-alkyl-indoles by sequential reactions. Gold-catalyzed sequential cyclization/alkylation, N-alkylation/cyclization, or N-alkylation/cyclization/alkylation reactions leading to different indoles can be directed by changing the 2-alkynyl-phenylamine 1/alpha,beta-enone 3 ratio and the reaction temperature. Unusual gold-catalyzed rearrangement reaction of indoles are observed at 140 degrees C. New gold-catalyzed formation of propargyl-alkyl ether under mild conditions and the hydration reaction of N-acetyl-2-ethynyl-phenylamine are reported.