2,9-bis<4-(6-methylpyridin-2-ylcarbamoyl)phenyl>-1,10-phenanthroline | 167496-52-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2,9-bis<4-(6-methylpyridin-2-ylcarbamoyl)phenyl>-1,10-phenanthroline
• 英文别名: N-(6-methylpyridin-2-yl)-4-[9-[4-[(6-methylpyridin-2-yl)carbamoyl]phenyl]-1,10-phenanthrolin-2-yl]benzamide
• CAS: 167496-52-8
• 化学式: C₃₈H₂₈N₆O₂
• 分子量: 600.679
• InChiKey: AOURPBOWFKRWTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  46
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tetrakis(acetonitrile)copper(I)tetrafluoroborate 、 2,9-bis<4-(6-methylpyridin-2-ylcarbamoyl)phenyl>-1,10-phenanthroline 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 以92%的产率得到
  参考文献：
  名称：

  Self-Assembling, Chromogenic Receptors for the Recognition of Dicarboxylic Acids

  摘要：

  The synthesis of ligands (2,9-disubstituted phenanthrolines) bearing one or two acylaminopyridine binding sites, compounds 1 and 2 respectively, is described. Each ligand can assemble on a Cu(I) template, forming two different receptors for dicarboxylic acids, Cu(1)(2)(BF4-)-B-+ and Cu(2)(2)(BF4-)-B-+. These orange Cu(I) complexes are shown to bind (K-a > 10(4) M(-1)) to a variety of dicarboxylic acids in chloroform, with a slight preference for the C-5-dicarboxylic acids, glutaric and N-CBz-glutamic acids, over shorter and longer substrates. Complexation is analyzed both by NMR chemical shift changes and UV-visible absorption changes. The data indicate formation of 1:1 complexes for Cu(1)(2)(BF4-)-B-+ and 2:1 complexes for Cu(2)(2)(BF4-)-B-+, with the dicarboxylic acid substrate hydrogen bonding simultaneously to an acylaminopyridine binding site on each ligand. For Cu(2)(2)(BF4-)-B-+, the complexation event results in large shifts in the visible absorption bands and a color change from orange to red. The change in the visible absorbance, and therefore the chromogenicity, was found to be substrate dependent. The chromogenic effect is explained by a conformational change in the receptors resulting from hydrogen bond formation with the substrate.

  DOI：

  10.1021/ja00137a021
• 作为产物：
  描述：

  29-双[P-(甲酰)苯基]-110-菲罗啉 在 草酰氯 、 四丁基高锰酸胺盐 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 2,9-bis<4-(6-methylpyridin-2-ylcarbamoyl)phenyl>-1,10-phenanthroline
  参考文献：
  名称：

  Self-Assembling, Chromogenic Receptors for the Recognition of Dicarboxylic Acids

  摘要：

  The synthesis of ligands (2,9-disubstituted phenanthrolines) bearing one or two acylaminopyridine binding sites, compounds 1 and 2 respectively, is described. Each ligand can assemble on a Cu(I) template, forming two different receptors for dicarboxylic acids, Cu(1)(2)(BF4-)-B-+ and Cu(2)(2)(BF4-)-B-+. These orange Cu(I) complexes are shown to bind (K-a > 10(4) M(-1)) to a variety of dicarboxylic acids in chloroform, with a slight preference for the C-5-dicarboxylic acids, glutaric and N-CBz-glutamic acids, over shorter and longer substrates. Complexation is analyzed both by NMR chemical shift changes and UV-visible absorption changes. The data indicate formation of 1:1 complexes for Cu(1)(2)(BF4-)-B-+ and 2:1 complexes for Cu(2)(2)(BF4-)-B-+, with the dicarboxylic acid substrate hydrogen bonding simultaneously to an acylaminopyridine binding site on each ligand. For Cu(2)(2)(BF4-)-B-+, the complexation event results in large shifts in the visible absorption bands and a color change from orange to red. The change in the visible absorbance, and therefore the chromogenicity, was found to be substrate dependent. The chromogenic effect is explained by a conformational change in the receptors resulting from hydrogen bond formation with the substrate.

  DOI：

  10.1021/ja00137a021

文献信息

• Self-Assembling, Chromogenic Receptors for the Recognition of Dicarboxylic Acids
  作者：M. Scott Goodman、Andrew D. Hamilton、Jean Weiss

  DOI：10.1021/ja00137a021

  日期：1995.8

  The synthesis of ligands (2,9-disubstituted phenanthrolines) bearing one or two acylaminopyridine binding sites, compounds 1 and 2 respectively, is described. Each ligand can assemble on a Cu(I) template, forming two different receptors for dicarboxylic acids, Cu(1)(2)(BF4-)-B-+ and Cu(2)(2)(BF4-)-B-+. These orange Cu(I) complexes are shown to bind (K-a > 10(4) M(-1)) to a variety of dicarboxylic acids in chloroform, with a slight preference for the C-5-dicarboxylic acids, glutaric and N-CBz-glutamic acids, over shorter and longer substrates. Complexation is analyzed both by NMR chemical shift changes and UV-visible absorption changes. The data indicate formation of 1:1 complexes for Cu(1)(2)(BF4-)-B-+ and 2:1 complexes for Cu(2)(2)(BF4-)-B-+, with the dicarboxylic acid substrate hydrogen bonding simultaneously to an acylaminopyridine binding site on each ligand. For Cu(2)(2)(BF4-)-B-+, the complexation event results in large shifts in the visible absorption bands and a color change from orange to red. The change in the visible absorbance, and therefore the chromogenicity, was found to be substrate dependent. The chromogenic effect is explained by a conformational change in the receptors resulting from hydrogen bond formation with the substrate.