2-氯-3-(4-乙氧基苯胺基)萘-1,4-二酮 | 6305-25-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-氯-3-(4-乙氧基苯胺基)萘-1,4-二酮
• 英文名称: 2-(4-ethoxyphenylamino)-3-chloro-1,4-naphthoquinone
• 英文别名: 2-chloro-3-(4-ethoxyphenylamino)-1,4-naphthoquinone；3--2-chlor-1,4-naphthochinon；2-Chlor-3-(4-aethoxy-anilino)-α-naphthochinon；2-Chloro-3-(4-ethoxyanilino)-1,4-dihydronaphthalene-1,4-dione；2-chloro-3-(4-ethoxyanilino)naphthalene-1,4-dione
• CAS: 6305-25-5
• 化学式: C₁₈H₁₄ClNO₃
• mdl: MFCD00029214
• 分子量: 327.767
• InChiKey: VEDXZWCOPQITOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氯-3-(4-乙氧基苯胺基)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 20.0h， 以40%的产率得到2-ethoxybenzo[b]phenazine-6,11-dione
  参考文献：
  名称：

  Synthesis and cytotoxicity of 6,11-Dihydro-pyrido- and 6,11-Dihydro-benzo[2,3-b]phenazine-6,11-dione derivatives

  摘要：

  6,11-Dihydro-pyrido[2,3-b]phenazine-6,11-diones and 6,11 -dihydro-benzo[2,3-b]phenazine-6,11-diones were synthesized from 6,7-dichloro-5,8-quinolinedione and 2,3-dichloro-1,4-naphthoquinone. The study on the cytotoxicity on these products revealed that the pyridophenazinediones, tetracyclic heteroquinone analogues with three nitrogen atoms exhibited a high cytotoxicity on several human tumor cell lines. Compound 9c and 9e showed in vitro antitumor activity comparable or superior to doxorubicin against the human ovarian tumor cells (SK-OV-3) and the human CNS cells (XF 498). The IC50 value for compound 9e,was 0.06 muM against the human CNS cells (XF 498), which was 2.6 times higher than that (0.16 muM) of doxorubicin. In addition, the X-ray crystallographic analysis of two phenazinedione derivatives (9b,c) showed clearly the exact position of the nucleophilic substitution of 6,7-dichloro-5,8-quinolinedione. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00028-2
• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 、 对乙氧基苯胺 以 乙醇 为溶剂， 反应 2.0h， 以87%的产率得到2-氯-3-(4-乙氧基苯胺基)萘-1,4-二酮
  参考文献：
  名称：

  角杂环。芳基氨基萘醌在苯并吩噻嗪合成中的应用

  摘要：

  通过2-氯-3-乙氧基苯胺基-1,4-萘醌与2-氨基硫酚的巯基锌在吡啶中的环缩合反应合成了取代的6-乙氧基苯胺基-5 H-苯并[a]吩噻嗪-5-酮（3a-f） 。介绍并讨论了nmr，ir和质谱数据。

  DOI：

  10.1002/jhet.5570200663

文献信息

• [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium/1,1′-Bis(diphenylphosphino)ferrocene Catalyzed Synthesis of 2,3-Diamino-1,4-naphthoquinones
  作者：John Reiner、Jun Chang、Xiao Wang、Xiu Zheng、Lei Wang、Wei Xie

  DOI：10.1055/s-2007-965983

  日期：2007.4

  coupling of 2-amino-3-chloro-1,4-naphthoquinones with amines is described. The scope and limitations of the coupling process using [1,1 '-bis(diphenylphosphino)ferrocene] dichloropalladium [PdCl 2 (dppf)], combined with 1,1'-bis(diphenylphosphino)ferrocene (dppf) as a ligand and sodium tert-butoxide as base were investigated, and found to catalyze efficiently the coupling of 2-(arylamino)-3-chloro- 1,4-naphthoquinones

  描述了一种通过 2-氨基-3-氯-1,4-萘醌与胺的钯催化偶联合成 2,3-二氨基-1,4-萘醌衍生物的一般方法。使用[1,1'-双(二苯基膦基)二茂铁]二氯钯[PdCl 2 (dppf)]与1,1'-双(二苯基膦基)二茂铁(dppf)作为配体和钠的偶联过程的范围和限制对作为碱的叔丁醇进行了研究，发现它可以有效地催化 2-(芳基氨基)-3-氯-1,4-萘醌与伯芳基胺和烷基胺的偶联。应用该程序获得了一系列以前无法获得的新型2,3-二氨基-1,4-萘醌衍生物。
• Synthesis of novel substituted naphthoquino[b]-benzo[e][1,4]diazepines via Pictet–Spengler cyclization
  作者：Xiao Lei Wang、Xiu Fang Zheng、Ren He Liu、John Reiner、Jun Biao Chang

  DOI：10.1016/j.tet.2007.02.002

  日期：2007.4

  Synthesis of novel 4,5-dihydro-1H-1,4-naphthoquino[b]-benzo[e][1,4]diazepine derivatives via Pictet–Spengler cyclization is reported. Reaction of 2,3-diamino-naphthoquinones with aldehydes in the presence of BF3·Et2O gives benzodiazepine-naphthoquinones in good yields.

  据报道，通过Pictet-Spengler环化反应合成了新的4,5-二氢-1 H -1,4-萘喹[ b ]-苯并[ e ] [1,4]二氮杂卓衍生物。在BF 3 ·Et 2 O的存在下2,3-二氨基萘醌与醛的反应可得到高产率的苯并二氮杂萘醌。
• 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.
• OERIU, Pharmazie, 1961, vol. 16, p. 266 - 272
  作者：OERIU

  DOI：——

  日期：——
• AGARWAL, N. L.;ATAL, C. K., J. HETEROCYCL. CHEM., 1983, 20, N 6, 1741-1744
  作者：AGARWAL, N. L.、ATAL, C. K.

  DOI：——

  日期：——