N,N'-bis(3,5-dichlorophenyl)pyridine-2,6-dicarboxamide

• 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: N,N'-bis(3,5-dichlorophenyl)pyridine-2,6-dicarboxamide
• 英文别名: 2-N,6-N-bis(3,5-dichlorophenyl)pyridine-2,6-dicarboxamide
• 化学式: C₁₉H₁₁Cl₄N₃O₂
• 分子量: 455.127
• InChiKey: ZHPYFYGWDOHUJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N'-bis(3,5-dichlorophenyl)pyridine-2,6-dicarboxamide 在 hexafluorophosphoric acid 作用下， 以 甲醇 、 水 为溶剂， 反应 0.25h， 生成 2,6-bis(3,5-dichlorophenylcarbamoyl)pyridinium
  参考文献：
  名称：

  Syntheses of amide based anion receptors and investigation of their associations with anions and their molecular structures using proton NMR titration and DFT methods

  摘要：

  The synthesized disubstituted isophthalamide and pyridine-2,6dicarboxamide derivatives of nine compounds were prepared. Their association constants with tetrabutylammonium fluoride (TBA center dot F), tetrabutylammonium chloride (TBA center dot Cl), tetrabutylammonium bromide (TBA center dot Br), tetrabutylammonium dihydrogenphosphate (TBA center dot H2PO4), tetrabutylammonium hydrogensulphate (TBA center dot HSO4) and tetrabutylammonium nitrate (TBA center dot NO3) were obtained by H-1 NMR titration technique. The optimized structures of compounds 1-9 and their association with F-, Cl-, Br-, H2PO4-, HSO4- and NO3- were obtained using the B3LYP/6-31+G(d) method. The most favorable complex of compound 3 with Br- was found. The high association constants of complexes 1-6 with F- are expected. Associations of all receptors with anions are exothermic and spontaneous reactions. Thermodynamic properties of all associations obtained using B3LYP/6-31+G(d) method are reported. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2013.12.060
• 作为产物：
  描述：

  2,6-氯甲酰吡啶 、 3,5-二氯苯胺 在 4-二甲氨基吡啶 、 三正丁胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以55%的产率得到N,N'-bis(3,5-dichlorophenyl)pyridine-2,6-dicarboxamide
  参考文献：
  名称：

  Syntheses of amide based anion receptors and investigation of their associations with anions and their molecular structures using proton NMR titration and DFT methods

  摘要：

  The synthesized disubstituted isophthalamide and pyridine-2,6dicarboxamide derivatives of nine compounds were prepared. Their association constants with tetrabutylammonium fluoride (TBA center dot F), tetrabutylammonium chloride (TBA center dot Cl), tetrabutylammonium bromide (TBA center dot Br), tetrabutylammonium dihydrogenphosphate (TBA center dot H2PO4), tetrabutylammonium hydrogensulphate (TBA center dot HSO4) and tetrabutylammonium nitrate (TBA center dot NO3) were obtained by H-1 NMR titration technique. The optimized structures of compounds 1-9 and their association with F-, Cl-, Br-, H2PO4-, HSO4- and NO3- were obtained using the B3LYP/6-31+G(d) method. The most favorable complex of compound 3 with Br- was found. The high association constants of complexes 1-6 with F- are expected. Associations of all receptors with anions are exothermic and spontaneous reactions. Thermodynamic properties of all associations obtained using B3LYP/6-31+G(d) method are reported. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2013.12.060

文献信息

• Cytotoxic small molecule dimers and their inhibitory activity against human breast cancer cells
  作者：M. Kyle Hadden、Brian S.J. Blagg

  DOI：10.1016/j.bmcl.2007.07.014

  日期：2007.9

  Small molecules based upon natural product dimers that exhibit cytotoxic activity were synthesized and evaluated for their anti-proliferative activity in human breast cancer cell lines. A central isophthalic core structure linking aromatic amines containing 3,5-disubstitutions produced the most active compounds. This series of compounds was found to be more active against the estrogen receptor positive cell line MCF-7 than the estrogen receptor negative cell line, SKBr3. (C)2007 Elsevier Ltd. All rights reserved.
• Syntheses of amide based anion receptors and investigation of their associations with anions and their molecular structures using proton NMR titration and DFT methods
  作者：Korakot Navakhun、Ranu Sawangsri、Vithaya Ruangpornvisuti

  DOI：10.1016/j.molstruc.2013.12.060

  日期：2014.3

  The synthesized disubstituted isophthalamide and pyridine-2,6dicarboxamide derivatives of nine compounds were prepared. Their association constants with tetrabutylammonium fluoride (TBA center dot F), tetrabutylammonium chloride (TBA center dot Cl), tetrabutylammonium bromide (TBA center dot Br), tetrabutylammonium dihydrogenphosphate (TBA center dot H2PO4), tetrabutylammonium hydrogensulphate (TBA center dot HSO4) and tetrabutylammonium nitrate (TBA center dot NO3) were obtained by H-1 NMR titration technique. The optimized structures of compounds 1-9 and their association with F-, Cl-, Br-, H2PO4-, HSO4- and NO3- were obtained using the B3LYP/6-31+G(d) method. The most favorable complex of compound 3 with Br- was found. The high association constants of complexes 1-6 with F- are expected. Associations of all receptors with anions are exothermic and spontaneous reactions. Thermodynamic properties of all associations obtained using B3LYP/6-31+G(d) method are reported. (C) 2013 Elsevier B.V. All rights reserved.