3,6-di[6-(1,8-naphthyrid-2-yl)pyridin-2-yl]pyridazine | 874379-30-3

• 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-di[6-(1,8-naphthyrid-2-yl)pyridin-2-yl]pyridazine
• 英文别名: 3,6-di(6-acetylpyrid-2-yl)pyridazine；1-[6-[6-(6-Acetylpyridin-2-yl)pyridazin-3-yl]pyridin-2-yl]ethanone
• CAS: 874379-30-3
• 化学式: C₁₈H₁₄N₄O₂
• 分子量: 318.335
• InChiKey: VIJVIPLMAHUPQK-UHFFFAOYSA-N

物化性质

• 熔点：
  269-270 °C
• 沸点：
  616.5±55.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  85.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,6-di[6-(1,8-naphthyrid-2-yl)pyridin-2-yl]pyridazine 、 8-胺基-7-醛基喹啉 在 四氢吡咯 作用下， 以 乙醇 为溶剂， 反应 30.0h， 以77%的产率得到3,6-bis(1',10'-phenanthrolin-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
• 作为产物：
  描述：

  2,6-二溴吡啶 在 四(三苯基膦)钯 正丁基锂 作用下， 以 乙二醇二甲醚 、 乙醚 、 正己烷 为溶剂， 反应 162.0h， 生成 3,6-di[6-(1,8-naphthyrid-2-yl)pyridin-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

• Direct Access to 4-Carboxy-1,8-naphthyridines and Related Compounds through Pfitzinger-Type Chemistry
  作者：Ruifa Zong、Hui Zhou、Randolph P. Thummel

  DOI：10.1021/jo800456r

  日期：2008.6.1

  The 4-carboxy-1,8-naphthyrid-2-yl moiety is a useful ligand component in that it promotes lower energy electronic absorption in its metal complexes and also provides a useful tether for anchoring the ligand to a semiconductor surface. The synthon [2-(pivaloylamino)pyrid-3-yl]oxoacetic acid ethyl ester can be easily obtained in two steps from 2-aminopyridine. The Pfitzinger-type condensation of this molecule with a 2-acetylazaaromatic species in ethanolic KOH, after acidification, directly provides bi- and tridentate ligands containing the 4-carboxy-1,8-naphthyrid-2-yl moiety.
• 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.