2-chloro-3-(2,4-dinitrophenylamino)-1,4-naphthoquinone | 488128-98-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-chloro-3-(2,4-dinitrophenylamino)-1,4-naphthoquinone
• 英文别名: 2-chloro-3-(2,4-dinitroanilino)-1,4-naphthoquinone；2-Chloro-3-(2,4-dinitroanilino)naphthoquinone；2-chloro-3-(2,4-dinitroanilino)naphthalene-1,4-dione
• CAS: 488128-98-9
• 化学式: C₁₆H₈ClN₃O₆
• mdl: MFCD03289648
• 分子量: 373.709
• InChiKey: LRXIEXKHUQKMSZ-UHFFFAOYSA-N

物化性质

• 沸点：
  526.9±50.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 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：
  138
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-chloro-3-(2,4-dinitrophenylamino)-1,4-naphthoquinone 在 sodium azide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以76%的产率得到2-amino-3-(2,4-dinitrophenylamino)-1,4-naphthoquinone
  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
• 作为产物：
  描述：

  2-氯-3-(苯基氨基)萘-1,4-二酮 在 硫酸 、 硝酸 作用下， 反应 2.0h， 以80%的产率得到2-chloro-3-(2,4-dinitrophenylamino)-1,4-naphthoquinone
  参考文献：
  名称：

  3-Arylamino-2-chloro-1,4-naphthoquinones 的直接硝化

  摘要：

  报道了标题化合物的单硝基和二硝基衍生物的方便两步合成。芳香胺与2,3-二氯-1,4-萘醌的迈克尔型加成，然后进行混合酸硝化，得到以前难以获得或无法获得的硝基芳香醌。

  DOI：

  10.1055/s-2005-865327

文献信息

• Synthesis and studies of the antifungal activity of 2-anilino-/2,3-dianilino-/2-phenoxy- and 2,3-diphenoxy-1,4-naphthoquinones
  作者：Elisa Leyva、Lluvia I. López、Ramón F. García de la Cruz、Claudia G. Espinosa-González

  DOI：10.1007/s11164-016-2732-3

  日期：2017.3

  Several synthetic and natural naphthoquinone derivatives have been associated with antifungal activity. Candida albicans is a fungus that is known to exist in the normal human flora, but under certain conditions it can cause mild to fatal infections. Its pathogenicity has been associated with fungus conversion from cellular yeast to filamentous form Y – M . Inhibition of this process by several anilino-

  几种合成的和天然的萘醌衍生物与抗真菌活性有关。 白色念珠菌 是一种已知存在于正常人类菌群中的真菌，但在某些条件下会引起轻度至致命的感染。其致病性与真菌从细胞酵母转化为丝状 Y – M有关 。为了发现结构，氧化还原性质和生物活性之间的相关性，研究了几种苯胺基，二苯胺基，苯氧基和二苯氧基-1,4-萘醌对这一过程的抑制作用。
• Palladium-Catalyzed Amination of 2,3-Dichloro-1,4-naphthoquinone with Nitroarylamines
  作者：John Reiner、Xiao-Lei Wang、Xiu-Fang Zheng

  DOI：10.1055/s-2006-939047

  日期：——

  A convenient one-step synthesis of 2-[(nitroaryl)amino]-3-chloro-1,4-naphthoquinones is reported. The direct amination of 2,3-dichloro-1,4-naphthoquinone with nitro-substituted aryl amines is catalyzed by PdCl 2 (dppf)/dppf 1 in the presence of t-BuONa as base to yield 2-[(nitroaryl)amino]-3-chloro-1,4-naphthoquinones, several of which were previously unavailable. Traces of the 2,3-di[(nitroaryl)amino]-1

  报告了 2-[(硝基芳基) 氨基]-3-氯-1,4-萘醌的方便一步合成。PdCl 2 (dppf)/dppf 1 在 t-BuONa 碱存在下催化 2,3-二氯-1,4-萘醌与硝基取代的芳胺直接胺化，生成 2-[(硝基芳基)氨基]-3-chloro-1,4-naphthoquinones，其中一些以前无法获得。检测到痕量 2,3-二[(硝基芳基)氨基]-1,4-萘醌作为副产物。
• Synthesis of novel 2-(fluoroanilino)-3-(2,4-dinitroanilino) derivatives of 1,4-naphthoquinone
  作者：Elisa Leyva、Kim M. Baines、Claudia G. Espinosa-González、Lluvia I. López、Diego A. Magaldi-Lara、Socorro Leyva

  DOI：10.1016/j.tetlet.2015.07.046

  日期：2015.9

  Several novel 2-(fluoroanilino)-3-(2,4-dinitroanilino) derivatives of 1,4-naphthoquinone have been synthesized in good to excellent yields. First, 2-chloro-3-(2,4-dinitroanilino)-1,4-naphthoquinone was prepared in two steps beginning with the reaction of 2,3-dichloro-1,4-naphthoquinone with aniline in the presence of a Lewis acid (CeCl3 center dot 7H(2)O). The resulting 2-(anilino)-1,4-naphthoquinone was then nitrated. The strong electron withdrawing effect of the 2,4-dinitroanilino substituent on the naphthoquinone framework facilitated the displacement of the second chlorine atom by a variety of weakly nucleophilic fluoro-substituted anilines under reflux conditions. (C) 2015 Published by Elsevier Ltd.
• Novel 2-amino-3-(2,4-dinitrophenylamino) derivatives of 1,4-naphthoquinone
  作者：Thida Win、Shmuel Bittner

  DOI：10.1016/j.tetlet.2005.03.041

  日期：2005.5

  The strong electron withdrawing nature of a 2,4-dinitrophenylamino group when attached to a chloro-naphthoquinone enhances the displacement of the chlorine atom by various aliphatic, cyclic and aromatic amines. A new series of 2-amino-3-(2,4-dinitrophenylamino) derivatives of 1,4-naphthoquinone were prepared. Three absorption maxima in the UV-vis spectra were typical, including one at 430-550 nm assigned to a CT transition. (c) 2005 Elsevier Ltd. All rights reserved.
• 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.