N¹-(4-fluorophenyl)-N⁴,N⁴-dimethylbenzene-1,4-diamine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N¹-(4-fluorophenyl)-N⁴,N⁴-dimethylbenzene-1,4-diamine
• 英文别名: 1-N-(4-fluorophenyl)-4-N,4-N-dimethylbenzene-1,4-diamine
• 化学式: C₁₄H₁₅FN₂
• 分子量: 230.285
• InChiKey: HKNQRHQTTQOHNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N,N-二甲基-对苯二胺 、 对溴氟苯 在 copper(I) oxide 、 N¹-benzyl-N²-(2-methylnaphthalen-1-yl)oxalamide 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以59%的产率得到N¹-(4-fluorophenyl)-N⁴,N⁴-dimethylbenzene-1,4-diamine
  参考文献：
  名称：

  Discovery of N-(Naphthalen-1-yl)-N′-alkyl Oxalamide Ligands Enables Cu-Catalyzed Aryl Amination with High Turnovers

  摘要：

  A Class of N-(naphthalen-1-yl)-N'-alkyl oxalamides have been proven to be powerful ligands, making a coupling reaction of (hetero)aryl iodides with primary amines proceed at 50 degrees C with only 0.01 mol % of Cu2O and ligand as well as a coupling reaction of (hetero)aryl bromides with primary amines and ammonia at 80 degrees C with only 0.1 mol % of Cu2O and ligand. A wide range of coupling partners work well under these conditions thereby providing an easy to operate method for preparing (hetero)atyl amines.

  DOI：

  10.1021/acs.orglett.7b00901

文献信息

• Preparation of diarylamines by the addition of 4-(N,N-dimethylamino)phenyllithium to nitroarenes
  作者：Tianle Yang、Bongsup P. Cho

  DOI：10.1016/j.tetlet.2003.07.002

  日期：2003.9

  The addition of 4-(N,N-dimethylamino)phenyllithium to nitroarenes in THF (−78°C) affords the corresponding diarylamines in one-pot and the reaction appears to be general in scope. A ‘nitroso’-based mechanism is proposed for this novel nitroreductive N-arylation reaction.

  在THF（-78°C）中向硝基芳烃中添加4-（N，N-二甲基氨基）苯基锂可在一锅中获得相应的二芳基胺，该反应似乎是一般性的。提出了一种基于“亚硝基”的机理用于这种新型的硝基还原N-芳基化反应。
• Discovery of <i>N</i>-(Naphthalen-1-yl)-<i>N</i>′-alkyl Oxalamide Ligands Enables Cu-Catalyzed Aryl Amination with High Turnovers
  作者：Jie Gao、Subhajit Bhunia、Kailiang Wang、Lu Gan、Shanghua Xia、Dawei Ma

  DOI：10.1021/acs.orglett.7b00901

  日期：2017.6.2

  A Class of N-(naphthalen-1-yl)-N'-alkyl oxalamides have been proven to be powerful ligands, making a coupling reaction of (hetero)aryl iodides with primary amines proceed at 50 degrees C with only 0.01 mol % of Cu2O and ligand as well as a coupling reaction of (hetero)aryl bromides with primary amines and ammonia at 80 degrees C with only 0.1 mol % of Cu2O and ligand. A wide range of coupling partners work well under these conditions thereby providing an easy to operate method for preparing (hetero)atyl amines.