2-amino-3-(4-chloroanilino)-naphthalene-1,4-dione | 442653-08-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-amino-3-(4-chloroanilino)-naphthalene-1,4-dione
• 英文别名: 2-amino-3-(4-chlorophenylamino)-1,4-naphthoquinone；2-Amino-3-[(4-chlorophenyl)amino]-1,4-dihydronaphthalene-1,4-dione；2-amino-3-(4-chloroanilino)naphthalene-1,4-dione
• CAS: 442653-08-9
• 化学式: C₁₆H₁₁ClN₂O₂
• mdl: MFCD05031028
• 分子量: 298.729
• InChiKey: WWZZPOCMSKAKRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氯-3-(4-氯苯胺基)萘-1,4-二酮 在 sodium azide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以75%的产率得到2-amino-3-(4-chloroanilino)-naphthalene-1,4-dione
  参考文献：
  名称：

  Thermolysis of 2-azido-3-(R-anilino)-1,4-naphthoquinones. Nitrene insertion versus hydrogen abstraction

  摘要：

  2-chloro-3-(R-anilino)-1,4-naphthoquinones react with sodium azide upon refluxing in DMF. The thermochemistry of 2-azido-3-(R-anilino)-1,4-naphthoquinone is strongly modified by the substituent on aniline. Having an strong electron-donor like O-R results in the generation of a phenazine while having an electron-withdrawing substituent results in the formation of 2-amino-3-(R-anilino)-1,4-naphthoquinone. The products obtained are explained in terms of singlet and/or triplet nitrene chemistry. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2020.151731

文献信息

• Thermolysis of 2-azido-3-(R-anilino)-1,4-naphthoquinones. Nitrene insertion versus hydrogen abstraction
  作者：Silvia E. Loredo-Carrillo、Elisa Leyva、Matthew S. Platz、Agobardo Cárdenas-Chaparro、Antonio Martínez-Richa

  DOI：10.1016/j.tetlet.2020.151731

  日期：2020.4

  2-chloro-3-(R-anilino)-1,4-naphthoquinones react with sodium azide upon refluxing in DMF. The thermochemistry of 2-azido-3-(R-anilino)-1,4-naphthoquinone is strongly modified by the substituent on aniline. Having an strong electron-donor like O-R results in the generation of a phenazine while having an electron-withdrawing substituent results in the formation of 2-amino-3-(R-anilino)-1,4-naphthoquinone. The products obtained are explained in terms of singlet and/or triplet nitrene chemistry. (C) 2020 Elsevier Ltd. All rights reserved.