4-chloro-N-(4-fluorophenyl)-2-nitrobenzamide | 333346-31-9

• 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: 4-chloro-N-(4-fluorophenyl)-2-nitrobenzamide
• CAS: 333346-31-9
• 化学式: C₁₃H₈ClFN₂O₃
• mdl: MFCD01215322
• 分子量: 294.67
• InChiKey: FGPVHNBGUQWFAV-UHFFFAOYSA-N

物化性质

• 沸点：
  360.4±42.0 °C(Predicted)
• 密度：
  1.501±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-chloro-N-(4-fluorophenyl)-2-nitrobenzamide 在 palladium on activated charcoal 三氯化铁 、 甲烷 、 一水合肼 作用下， 以 甲醇 为溶剂， 生成 NH₂C₆H₃ClCONHC₆H₄F
  参考文献：
  名称：

  Inhibitors of type III secretion in Yersinia: Design, synthesis and multivariate QSAR of 2-arylsulfonylamino-benzanilides

  摘要：

  Compound 1, 2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-5-chloro-N-(3,4-dichloro-phenyl)-benzamide. was identified as a putative type III secretion inhibitor in Yersinia. and the compound thus has a potential to be used to prevent or treat bacterial infections. A set of seven analogues was svnthesized and evaluated in a type III secretion dependent reporter-gene assay with viable bacterial to give basic SAR. A second set of 19 compounds was obtained by statistical molecular design in the building block and product space and by subsequent synthesis. Evaluation in the reporter-gene assay showed that the compounds ranged from nonactive to compounds more potent than 1. Based on the data multivariate QSAR models were established and the final Hi-PLS model showed good correlation between experimentally determined % inhibition and the calculated % inhibition of the reporter-gene signal. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.07.047
• 作为产物：
  描述：

  4-氯-2-硝基苯甲酸 、 4-氟苯胺 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-chloro-N-(4-fluorophenyl)-2-nitrobenzamide
  参考文献：
  名称：

  Inhibitors of type III secretion in Yersinia: Design, synthesis and multivariate QSAR of 2-arylsulfonylamino-benzanilides

  摘要：

  Compound 1, 2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-5-chloro-N-(3,4-dichloro-phenyl)-benzamide. was identified as a putative type III secretion inhibitor in Yersinia. and the compound thus has a potential to be used to prevent or treat bacterial infections. A set of seven analogues was svnthesized and evaluated in a type III secretion dependent reporter-gene assay with viable bacterial to give basic SAR. A second set of 19 compounds was obtained by statistical molecular design in the building block and product space and by subsequent synthesis. Evaluation in the reporter-gene assay showed that the compounds ranged from nonactive to compounds more potent than 1. Based on the data multivariate QSAR models were established and the final Hi-PLS model showed good correlation between experimentally determined % inhibition and the calculated % inhibition of the reporter-gene signal. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.07.047

文献信息

• An efficient synthesis of quinazoline-2,4-dione derivatives with the aid of a low-valent titanium reagent
  作者：Da-Qing Shi、Guo-Lan Dou、Zheng-Yi Li、Sai-Nan Ni、Xiao-Yue Li、Xiang-Shan Wang、Hui Wu、Shun-Jun Ji

  DOI：10.1016/j.tet.2007.07.011

  日期：2007.9

  A facile synthetic method using low-valent titanium reagent (TiCl4/Zn system) to promote the novel reductive cyclization of 2-nitrobenzamides and triphosgene is described. Sequentially, a series of quinazoline-2,4-diones were synthesized in good yields.

  描述了一种使用低价钛试剂（TiCl 4 / Zn系统）促进2-硝基苯甲酰胺和三光气新型还原环化的简便合成方法。依次，以高收率合成了一系列的喹唑啉-2,4-二酮。
• Efficient and Convenient Synthesis of Pyrrolo[1,2-<i>a</i>]quinazoline Derivatives with the Aid of Tin(II) Chloride
  作者：Manman Wang、Guolan Dou、Daqing Shi

  DOI：10.1021/cc100062e

  日期：2010.7.12

  An efficient, convenient, one-pot synthesis of 2,3,3a,4-tetrahydropyrrolo[1,2-a]quinazolin-5(1H)-one and 2,3,3a,4-tetrahydropyrrolo[1,2-a]quinazoline-1,5-dione was accomplished in good yields via the novel reductive cyclization of 2-nitrobenzamides with haloketones or keto acids mediated by SnCl2·2H2O system. A variety of substrates can participate in the process with good yields, making this methodology

  2,3,3a，4-四氢吡咯并[1,2 - a ]喹唑啉-5（1 H）-one和2,3,3a，4-四氢吡咯并[1,2-通过由SnCl 2 ·2H 2 O系统介导的2-硝基苯甲酰胺与卤代酮或酮酸的新型还原性环化反应，可以成功地制得]]喹唑啉-1,5-二酮。多种底物可以高收率参与该过程，从而使该方法适用于药物发现工作中的文库合成。
• Efficient and convenient synthesis of spiroindolinone-quinazolines induced by stannous chloride
  作者：Yu Hu、Man-Man Wang、Hui Chen、Da-Qing Shi

  DOI：10.1016/j.tet.2011.09.130

  日期：2011.12

  An efficient, convenient, one-pot synthesis of 1′H-spiro[indoline-3,2′-quinazoline]-2,4′(3′H)-dione derivatives was accomplished in good yields via the novel reductive cyclization of 2-nitrobenzamides and isatins mediated by SnCl2·2H2O system. A variety of substrates can participate in the process with good yields, making this methodology have broad applicability. The structure of compound 3c has been

  一种高效，方便，单釜1的合成“ ħ -螺[二氢吲哚-3,2'-喹唑啉] -2,4-'（3' ħ） -二酮衍生物是在良好的产率通过的2新颖还原环化完成SnCl 2 ·2H 2 O系统介导的硝基硝基苯甲酰胺和靛红。多种基材可以高产率参与该工艺，从而使该方法具有广泛的适用性。化合物3c的结构已经通过X射线衍射分析确认。
• Inhibitors of type III secretion in Yersinia: Design, synthesis and multivariate QSAR of 2-arylsulfonylamino-benzanilides
  作者：Anna M. Kauppi、C. David Andersson、Henrik A. Norberg、Charlotta Sundin、Anna Linusson、Mikael Elofsson

  DOI：10.1016/j.bmc.2007.07.047

  日期：2007.11

  Compound 1, 2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-5-chloro-N-(3,4-dichloro-phenyl)-benzamide. was identified as a putative type III secretion inhibitor in Yersinia. and the compound thus has a potential to be used to prevent or treat bacterial infections. A set of seven analogues was svnthesized and evaluated in a type III secretion dependent reporter-gene assay with viable bacterial to give basic SAR. A second set of 19 compounds was obtained by statistical molecular design in the building block and product space and by subsequent synthesis. Evaluation in the reporter-gene assay showed that the compounds ranged from nonactive to compounds more potent than 1. Based on the data multivariate QSAR models were established and the final Hi-PLS model showed good correlation between experimentally determined % inhibition and the calculated % inhibition of the reporter-gene signal. (C) 2007 Elsevier Ltd. All rights reserved.