2-(3,4-二甲基苯基氨基)-3-氯-1,4-萘醌 | 64505-78-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-(3,4-二甲基苯基氨基)-3-氯-1,4-萘醌
• 英文名称: 2-(3,4-dimethylphenylamino)-3-chloro-1,4-naphthoquinone
• 英文别名: 2-Chloro-3-(3,4-dimethylanilino)naphthoquinone；2-chloro-3-(3,4-dimethylanilino)naphthalene-1,4-dione
• CAS: 64505-78-8
• 化学式: C₁₈H₁₄ClNO₂
• 分子量: 311.768
• InChiKey: JVEZZWGCCORJLP-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：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3,4-二甲基苯基氨基)-3-氯-1,4-萘醌 在 sodium azide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以39%的产率得到1,2-Dimethyl-benzo[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 、 3,4-二甲基苯胺 以 乙醇 为溶剂， 反应 5.0h， 以85%的产率得到2-(3,4-二甲基苯基氨基)-3-氯-1,4-萘醌
  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

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 and cytotoxicity of 6,11-Dihydro-pyrido- and 6,11-Dihydro-benzo[2,3-b]phenazine-6,11-dione derivatives
  作者：Young-Shin Kim、Se-Young Park、Hyun-Jung Lee、Myung-Eun Suh、Dieter Schollmeyer、Chong-Ock Lee

  DOI：10.1016/s0968-0896(03)00028-2

  日期：2003.4

  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.