1,2-bis(isoquinoline-1-carboxamido)-4,5-dimethoxybenzene | 1258939-95-5

• 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: 1,2-bis(isoquinoline-1-carboxamido)-4,5-dimethoxybenzene
• 英文别名: N-[2-(isoquinoline-1-carbonylamino)-4,5-dimethoxyphenyl]isoquinoline-1-carboxamide
• CAS: 1258939-95-5
• 化学式: C₂₈H₂₂N₄O₄
• 分子量: 478.507
• InChiKey: OIOVJCHCEYBBGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  水合三氯化钌 、 1,2-bis(isoquinoline-1-carboxamido)-4,5-dimethoxybenzene 、 氧化亚氮 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到[(1,2-bis(isoquinoline-1-carboxamido)-4,5-dimethoxybenzene(2-))Ru(NO)(Cl)]
  参考文献：
  名称：

  Dye-Tethered Ruthenium Nitrosyls Containing Planar Dicarboxamide Tetradentate N4 Ligands: Effects of In-Plane Ligand Twist on NO Photolability

  摘要：

  To examine the steric effects of the in-plane ligands in dye-sensitized {RuNO}(6) nitrosyls on their NO photolability, two new ligands, namely, 1,2-Bis(pyridine-2-carboxamido)-4,5-dimethogbenzene (H-2(OMe)(2)bpb) and 1,2-Bis(lsoquinoline-1-carboxarnido)-4,5-dimethoxybenzene (H-2(OMe)(2)IQ1, H's are dissociable carboxamide protons) have been designed and synthesized. The syntheses and spectroscopic properties of {RuNO}(6) nitrosyls derived from these two ligands, namely, [((OMe)(2)bpb)Ru(NO)(Cl)] (4-Cl), [((OMe)(2)IQ1)Ru(NO)(Cl)] (5-Cl), [((OMe)(2)bpb)Ru(NO)(Resf)] (4-Resf), and [((OMe)(2)IQ1)Ru(NO)(Resf)] (5-Resf), are reported. The structures of 5-Cl, 4-Rest, and 5-Resf have been determined by X-ray crystallography. Removal of the in-plane ligand twist in the quinoline-based R(2)bQb(2-) ligand frame (because of steric interactions between the extended quinoline ring systems) in both R(2)bpb(2-) and R(2)IQ1(2-) (pyridine and 1-isoquinoline rings, respectively, instead of quinoline rings in the equatorial plane) results in enhanced solution stability, as well as higher quantum yield values for NO photorelease upon exposure to 500 nm light. Both dye-tethered {RuNO}(6) nitrosyls 4-Rest and 5-Rest exhibit greater sensitivity to visible light compared to the chloro-bound species 44:1 and 5-Cl. In addition, the dye-tethered nitrosyls are fluorescent and hence can be used as trackable NO donors in cellular studies.

  DOI：

  10.1021/ic1019873
• 作为产物：
  描述：

  异喹啉羧酸 、 1,2-二氨基-4,5-二甲氧基苯 在 吡啶 、 亚磷酸三苯酯 作用下， 反应 4.0h， 以60%的产率得到1,2-bis(isoquinoline-1-carboxamido)-4,5-dimethoxybenzene
  参考文献：
  名称：

  Dye-Tethered Ruthenium Nitrosyls Containing Planar Dicarboxamide Tetradentate N4 Ligands: Effects of In-Plane Ligand Twist on NO Photolability

  摘要：

  To examine the steric effects of the in-plane ligands in dye-sensitized {RuNO}(6) nitrosyls on their NO photolability, two new ligands, namely, 1,2-Bis(pyridine-2-carboxamido)-4,5-dimethogbenzene (H-2(OMe)(2)bpb) and 1,2-Bis(lsoquinoline-1-carboxarnido)-4,5-dimethoxybenzene (H-2(OMe)(2)IQ1, H's are dissociable carboxamide protons) have been designed and synthesized. The syntheses and spectroscopic properties of {RuNO}(6) nitrosyls derived from these two ligands, namely, [((OMe)(2)bpb)Ru(NO)(Cl)] (4-Cl), [((OMe)(2)IQ1)Ru(NO)(Cl)] (5-Cl), [((OMe)(2)bpb)Ru(NO)(Resf)] (4-Resf), and [((OMe)(2)IQ1)Ru(NO)(Resf)] (5-Resf), are reported. The structures of 5-Cl, 4-Rest, and 5-Resf have been determined by X-ray crystallography. Removal of the in-plane ligand twist in the quinoline-based R(2)bQb(2-) ligand frame (because of steric interactions between the extended quinoline ring systems) in both R(2)bpb(2-) and R(2)IQ1(2-) (pyridine and 1-isoquinoline rings, respectively, instead of quinoline rings in the equatorial plane) results in enhanced solution stability, as well as higher quantum yield values for NO photorelease upon exposure to 500 nm light. Both dye-tethered {RuNO}(6) nitrosyls 4-Rest and 5-Rest exhibit greater sensitivity to visible light compared to the chloro-bound species 44:1 and 5-Cl. In addition, the dye-tethered nitrosyls are fluorescent and hence can be used as trackable NO donors in cellular studies.

  DOI：

  10.1021/ic1019873