N,N-diethyl-2-(4-methoxylphenyl)benzofuran-3-amine | 1286763-69-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: N,N-diethyl-2-(4-methoxylphenyl)benzofuran-3-amine
• 英文别名: N,N-diethyl-2-(4-methoxyphenyl)-1-benzofuran-3-amine
• CAS: 1286763-69-6
• 化学式: C₁₉H₂₁NO₂
• 分子量: 295.381
• InChiKey: GQGLIIGWVKOZLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  25.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二乙氨基苯甲酸盐 、 2-[(4-methoxyphenyl)ethynyl]phenol 在 copper(II) bis(trifluoromethanesulfonate) 、 lithium tert-butoxide 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 4.0h， 以71%的产率得到N,N-diethyl-2-(4-methoxylphenyl)benzofuran-3-amine
  参考文献：
  名称：

  Copper-Catalyzed Direct Amination of Polyfluoroarenes and Azoles with Hydroxylamines and Its Application to the Synthesis of 3-Aminobenzoheteroles

  摘要：

  开发了一种铜催化的亲电性乌姆堡胺化策略，用于直接实现多氟芳烃和1,3-唑的C-H胺化。基于铜的胺化反应具有鲁棒性，可以轻松地在克规模上扩大规模。还描述了其在邻炔基苯酚和苯胺的累积亲电胺化反应中的应用，用于合成3-氨基苯并呋喃和吲哚。

  DOI：

  10.1055/s-0031-1289715

文献信息

• Copper-Catalyzed Direct Amination of Polyfluoroarenes and Azoles with Hydroxylamines and Its Application to the Synthesis of 3-Aminobenzoheteroles
  作者：Koji Hirano、Masahiro Miura、Naoki Matsuda、Tetsuya Satoh

  DOI：10.1055/s-0031-1289715

  日期：2012.6

  A copper-catalyzed electrophilic, umpolung amination strategy for the direct C-H amination of polyfluoroarenes and 1,3-azoles has been developed. The copper-based amination reaction is robust and can be easily scaled up on a gram scale. Its application to an annulative electrophilic amination of o-alkynylphenols and -anilines for the synthesis of 3-aminobenzofurans and -indoles is also described.

  开发了一种铜催化的亲电性乌姆堡胺化策略，用于直接实现多氟芳烃和1,3-唑的C-H胺化。基于铜的胺化反应具有鲁棒性，可以轻松地在克规模上扩大规模。还描述了其在邻炔基苯酚和苯胺的累积亲电胺化反应中的应用，用于合成3-氨基苯并呋喃和吲哚。
• Copper-Catalyzed Annulative Amination of <i>ortho</i>-Alkynylphenols with Hydroxylamines: Synthesis of 3-Aminobenzofurans by Umpolung Amination Strategy
  作者：Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/ol200651r

  日期：2011.5.6

  A room temperature copper-catalyzed annulative amination of ortho-alkynylphenols with electrophilic amination reagents, O-acylated hydroxylamines, proceeds efficiently to provide the corresponding 3-aminobenzofurans of biological and pharmaceutical interest.
• An Annulative Electrophilic Amination Approach to 3-Aminobenzoheteroles
  作者：Naoki Matsuda、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/jo202207s

  日期：2012.1.6

  A copper-catalyzed annulative amination approach to 3-aminobenzofurans and -indoles from o-alkynylphenols and -anilines has been developed. The Cu-based catalysis is based on an umpolung, electrophilic amination with O-benzoyl hydroxylamines and enables the mild and convergent synthesis of various 3-aminobenzoheteroles of biological and pharmaceutical interest. Some mechanistic investigations and an application of this protocol to construction of more complex tricyclic framework are also described.