1-(4-nitrophenyl)-2,2-di(1H-indole-3-yl)ethanone | 1375459-87-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-nitrophenyl)-2,2-di(1H-indole-3-yl)ethanone
• 英文别名: 1-(4-nitrophenyl)-2,2-di(1H-indol-3-yl)ethanone；2,2-di(1H-indol-3-yl)-1-(4-nitrophenyl)ethanone；2,2-bis(1H-indol-3-yl)-1-(4-nitrophenyl)ethanone
• CAS: 1375459-87-2
• 化学式: C₂₄H₁₇N₃O₃
• 分子量: 395.417
• InChiKey: OIMYYPUAMBXXPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  94.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吲哚 、 对硝基苯乙酮 在 碘 作用下， 以 二甲基亚砜 为溶剂， 以75%的产率得到1-(4-nitrophenyl)-2,2-di(1H-indole-3-yl)ethanone
  参考文献：
  名称：

  Metal-Free sp³ C–H Bond Dual-(Het)arylation: I₂-Promoted Domino Process to Construct 2,2-Bisindolyl-1-arylethanones

  摘要：

  A molecular I-2-promoted sp(3) C-H bond dual-(het)arylation protocol was developed for the synthesis of 2,2-bisindolyl-1-arylethanones. Through a logical design, three mechanism-different reactions (iodination, Kornblum oxidation, and Friedel Crafts reaction) were assembled in a single reactor. A variety of 2,2-bisindolyl-1-aryl ethanones were synthesized from simple and readily available aryl methyl ketones and indoles. In the reaction, metal, base, and ligand were all avoidable.

  DOI：

  10.1021/ol301366p

文献信息

• Ag Nanoparticles: An Efficient and Versatile Reagent for Synthesis of Bis(indolyl)methanes
  作者：Bahareh Sadeghi、Fereshteh Amiri Tavasoli、Alireza Hassanabadi

  DOI：10.1080/15533174.2015.1016315

  日期：2015.9.2

  Ag nanoparticles are found to be an efficient catalyst for the electrophilic substitution reaction of indole with aldehydes to afford the corresponding bis(indolyl)methanes in good yields. The remarkable features of this new procedure are high conversions, shorter reaction times, cleaner reaction profiles, and simple experimental and work-up procedures.

  发现Ag纳米颗粒是吲哚与醛的亲电取代反应的有效催化剂，以高收率提供相应的双（吲哚基）甲烷。这种新方法的显着特征是高转化率，较短的反应时间，更清洁的反应曲线以及简单的实验和后处理程序。
• B(HSO₄)₃as an Efficient Catalyst for the Syntheses of Bis(1<i>H</i>-Indol-3-yl)ethanones and Bis(benzotriazol-1-yl)ethanones
  作者：Mohammad Hossein Mosslemin、Abolfazl Eshghi Movahhed

  DOI：10.1155/2012/739603

  日期：——

  Efficient syntheses of bis (1H-indol-3-yl)ethanones and bis (benzotriazolyl)ethanones via reaction of phenylglyoxals with indole or 1,H-benzotriazole in the presence B(HSO₄)₃in solvent-free thermal and in aqueous media conditions are discribed. The syntheses have several advantages such as: generality, short reaction time, simple experiment and work-up procedures, excellent isolated yields.

  使用苯基乙酰乙酸与吲哚或1，H-苯并三氮唑在无溶剂热条件或水介质条件下，在B（HSO4）3的存在下高效合成了双（1H-吲哚-3-基）乙酮和双（苯并三氮唑基）乙酮。这些合成具有多种优点，如通用性、反应时间短、实验和工作程序简单、所得产物收率高。
• Metal-Free sp³ C–H Bond Dual-(Het)arylation: I₂-Promoted Domino Process to Construct 2,2-Bisindolyl-1-arylethanones
  作者：Yan-ping Zhu、Mei-cai Liu、Feng-cheng Jia、Jing-jing Yuan、Qing-he Gao、Mi Lian、An-xin Wu

  DOI：10.1021/ol301366p

  日期：2012.7.6

  A molecular I-2-promoted sp(3) C-H bond dual-(het)arylation protocol was developed for the synthesis of 2,2-bisindolyl-1-arylethanones. Through a logical design, three mechanism-different reactions (iodination, Kornblum oxidation, and Friedel Crafts reaction) were assembled in a single reactor. A variety of 2,2-bisindolyl-1-aryl ethanones were synthesized from simple and readily available aryl methyl ketones and indoles. In the reaction, metal, base, and ligand were all avoidable.