3,6-bis-[6'-(1'',8''-naphthyrid-2''-yl)-pyrid-2'-yl]pyridazine | 866403-81-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3,6-bis-[6'-(1'',8''-naphthyrid-2''-yl)-pyrid-2'-yl]pyridazine
• 英文别名: 3,6-bis[6'-(1'',8''-naphthyrid-2''-yl)pyrid-2'-yl]pyridazine；3,6-di[6-acetylpyridin-2-yl]pyridazine；2-[6-[6-[6-(1,8-Naphthyridin-2-yl)pyridin-2-yl]pyridazin-3-yl]pyridin-2-yl]-1,8-naphthyridine
• CAS: 866403-81-8
• 化学式: C₃₀H₁₈N₈
• 分子量: 490.527
• InChiKey: KKKDKUFETPMZOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  38
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,6-bis-[6'-(1'',8''-naphthyrid-2''-yl)-pyrid-2'-yl]pyridazine 、 ammonium hexafluorophosphate 、 4-三氟甲基吡啶 、 dichlorotetrakis(dimethylsulfoxide)ruthenium(II) 在 三乙胺 作用下， 以 乙醇 为溶剂， 以44%的产率得到
  参考文献：
  名称：

  A New Family of Ru Complexes for Water Oxidation

  摘要：

  Reaction of the bridging ligand 3,6-bis-[6'-(1' ',8' '-naphthyrid-2' '-yl)-pyrid-2'-yl]pyridazine (1) with [Ru(DMSO)4Cl2] in aqueous ethanol followed by excess 4-substituted pyridine (4-R-py) in the presence of triethylamine provides a series of three well-organized dinuclear complexes characterized by 1H NMR, MS, and X-ray. Mononuclear analogues are prepared from 4-tert-butyl-2,6-di(1',8'-naphthyrid-2'-yl)pyridine (5) and characterized in a similar fashion. All six complexes show electronic absorption and redox properties consistent with the electron donor/acceptor ability of the axial 4-R-py ligand. When an acetonitrile solution of the catalyst is added to an aqueous Ce(IV)-CF3SO3H solution (pH = 1.0) at 24 degrees C, oxygen evolution is observed for both mono and dinuclear systems. Turnover numbers range from 50 to 3200 with the best results being found when the axial ligand is 4-methylpyridine (mononuclear TN = 580 and dinuclear TN = 3200).

  DOI：

  10.1021/ja054791m
• 作为产物：
  描述：

  2,6-二溴吡啶 在 四(三苯基膦)钯 氢氧化钾 、 正丁基锂 作用下， 以 乙二醇二甲醚 、 乙醚 、 乙醇 、 正己烷 为溶剂， 反应 186.0h， 生成 3,6-bis-[6'-(1'',8''-naphthyrid-2''-yl)-pyrid-2'-yl]pyridazine
  参考文献：
  名称：

  Synthetic Approaches to Polypyridyl Bridging Ligands with Proximal Multidentate Binding Sites

  摘要：

  A series of 12 bridging ligands was prepared. These ligands include a central linker appended to two 1,8-naphthyrid-2-yl or two 1,10-phenanthrolin-2-yl units. The linkers include pyridazin-3.6-diyl, 1,8-naphthyrid-2,7-diyl, 2,2'-bipyrid-6,6'-diyl, 1, 10-phenanthrolin-2,9-diyl, 1,2-di(2'-pyrid-6'-yl)ethyne, and 3,6-di(2'-pyrid-6'-yl)pyridazine. The ligands were synthesized from the diacetyl derivative of the central linker by a Friedlander condensation with either 2-aminonicotinaldehyde or 8-amino-7-quinolinecarbaldehyde. The precursor diacetyl derivatives were, in turn, prepared by pathways involving Stille and Sonogashira couplings. Examination of the electronic absorption spectra of the bridging ligands shows the strongest correlation to be between pairs of ligands having the same central linker. Complexation studies will follow.

  DOI：

  10.1021/jo051937r

文献信息

• Preparation and Study of a Family of Dinuclear Ru(II) Complexes That Catalyze the Decomposition of Water
  作者：Zeping Deng、Huan-Wei Tseng、Ruifa Zong、Dong Wang、Randolph Thummel

  DOI：10.1021/ic7010875

  日期：2008.3.1

  self-assemble with two Ru(II) centers bridged by a Cl ion in the equatorial plane and four axial monodentate substituted pyridines or N-methylimidazoles to form the well-organized catalyst complexes. These complexes are characterized by their distinctive (1)H NMR spectra as well as an X-ray structure of one representative species. The photophysical and electrochemical features of these complexes are consistent

  开发了一种用于水的四电子氧化以提供涉及两个Ru（II）中心并置的双氧的方法，以使与金属结合的水分子可能与一种或两种金属相互作用。这种方法的关键要素是适当的桥联配体，它将在整个氧化还原循环中保持金属组件完整无缺。最终制备了四个紧密相关的双三齿聚吡啶型系统，其中配体的桥联和末端部分均发生变化，描述了针对此类配体的各种合成方法。所有这些配体通过在赤道平面上被Cl离子桥接的两个Ru（II）中心和四个轴向单齿取代的吡啶或N-甲基咪唑自组装，形成结构良好的催化剂配合物。这些配合物的特征在于其独特的（1）H NMR光谱以及一种代表性物种的X射线结构。这些配合物的光物理和电化学特征与在赤道和轴向配体中的电负性和离域作用一致。在研究的14种络合物中，除2种以外的所有络合物均包含四个轴向N-甲基咪唑配体，它们在pH = 1的过量Ce（IV）作为牺牲氧化剂的存在下催化水的分解。测量催化剂的周转数（TNs）。对于
• A New Family of Ru Complexes for Water Oxidation
  作者：Ruifa Zong、Randolph P. Thummel

  DOI：10.1021/ja054791m

  日期：2005.9.1

  Reaction of the bridging ligand 3,6-bis-[6'-(1' ',8' '-naphthyrid-2' '-yl)-pyrid-2'-yl]pyridazine (1) with [Ru(DMSO)4Cl2] in aqueous ethanol followed by excess 4-substituted pyridine (4-R-py) in the presence of triethylamine provides a series of three well-organized dinuclear complexes characterized by 1H NMR, MS, and X-ray. Mononuclear analogues are prepared from 4-tert-butyl-2,6-di(1',8'-naphthyrid-2'-yl)pyridine (5) and characterized in a similar fashion. All six complexes show electronic absorption and redox properties consistent with the electron donor/acceptor ability of the axial 4-R-py ligand. When an acetonitrile solution of the catalyst is added to an aqueous Ce(IV)-CF3SO3H solution (pH = 1.0) at 24 degrees C, oxygen evolution is observed for both mono and dinuclear systems. Turnover numbers range from 50 to 3200 with the best results being found when the axial ligand is 4-methylpyridine (mononuclear TN = 580 and dinuclear TN = 3200).
• Synthetic Approaches to Polypyridyl Bridging Ligands with Proximal Multidentate Binding Sites
  作者：Ruifa Zong、Dong Wang、Richard Hammitt、Randolph P. Thummel

  DOI：10.1021/jo051937r

  日期：2006.1.1

  A series of 12 bridging ligands was prepared. These ligands include a central linker appended to two 1,8-naphthyrid-2-yl or two 1,10-phenanthrolin-2-yl units. The linkers include pyridazin-3.6-diyl, 1,8-naphthyrid-2,7-diyl, 2,2'-bipyrid-6,6'-diyl, 1, 10-phenanthrolin-2,9-diyl, 1,2-di(2'-pyrid-6'-yl)ethyne, and 3,6-di(2'-pyrid-6'-yl)pyridazine. The ligands were synthesized from the diacetyl derivative of the central linker by a Friedlander condensation with either 2-aminonicotinaldehyde or 8-amino-7-quinolinecarbaldehyde. The precursor diacetyl derivatives were, in turn, prepared by pathways involving Stille and Sonogashira couplings. Examination of the electronic absorption spectra of the bridging ligands shows the strongest correlation to be between pairs of ligands having the same central linker. Complexation studies will follow.