5,5'-bis(2,2':6',2''-terpyridin-4'-ylethynyl)-2,2'-bipyridine | 162318-27-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5,5'-bis(2,2':6',2''-terpyridin-4'-ylethynyl)-2,2'-bipyridine
• 英文别名: 4-[2-[6-[5-[2-(2,6-Dipyridin-2-ylpyridin-4-yl)ethynyl]pyridin-2-yl]pyridin-3-yl]ethynyl]-2,6-dipyridin-2-ylpyridine；4-[2-[6-[5-[2-(2,6-dipyridin-2-ylpyridin-4-yl)ethynyl]pyridin-2-yl]pyridin-3-yl]ethynyl]-2,6-dipyridin-2-ylpyridine
• CAS: 162318-27-6
• 化学式: C₄₄H₂₆N₈
• 分子量: 666.744
• InChiKey: PECKISPQEKLHFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  52
• 可旋转键数：
  9
• 环数：
  8.0
• 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：

  铁粉 、 5,5'-bis(2,2':6',2''-terpyridin-4'-ylethynyl)-2,2'-bipyridine 以 not given 为溶剂， 生成
  参考文献：
  名称：

  Romero, Francisco M.; Ziessel, Raymond; Dupont-Gervais, Annick, Journal of the Chemical Society. Chemical communications

  摘要：

  DOI：
• 作为产物：
  描述：

  4'-[(trimethylsilyl)ethynyl]-2,2':6',2''-terpyridine 在 potassium fluoride 、 四(三苯基膦)钯 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 生成 5,5'-bis(2,2':6',2''-terpyridin-4'-ylethynyl)-2,2'-bipyridine
  参考文献：
  名称：

  Construction of Preorganized Polytopic Ligands via Palladium-Promoted Cross-Coupling Reactions

  摘要：

  Rigid preorganized multitopic ligands have been designed and synthesized. The Pd(O)-catalyzed cross-coupling reactions between ethynylated derivatives of bipyridine or terpyridine and the corresponding bipyridine or terpyridine halides or triflates provide access to various homo-ditopic, hetero-ditopic, homo-tritopic, and hetero-tritopic ligands bearing acetylene or diphenylacetylene central units in fair to excellent yields. Optimal conditions mere found with [Pd(PPh(3))(2)Cl-2], CuI in THF and diisopropylamine at rt, or with [Pd(PPh(3))(4)] in benzene and diisopropylamine at 80 degrees C. When a phenylethynyl group is present in the molecule, the relevant conditions involve [Pd(PPh(3))(4)] in n-propylamine at 60 degrees C. Oxidative dimerization of the ethynylated derivatives in the presence of cupric salts and oxygen gives the corresponding homo-ditopic ligands bearing diacetylene or diphenyldiacetylene as a spacer in good yields. These methods provide a practical approach to the rational design of multichelating ligands for coordination of redox and photoactive transition metals.

  DOI：

  10.1021/jo962068w

文献信息

• Preparation of novel mixed tritopic oligopyridine ligands built with chelating spacers and using palladium(0) catalysed coupling reactions
  作者：Francisco M. Romero、Raymond Ziessel

  DOI：10.1016/0040-4039(94)88466-8

  日期：1994.12

  The synthesis and characterization of tritopic ligands, obtained by connecting two terpyridines or two bipyridines with a bis-substituted-ethynyl-bipyridine or bis-substituted-ethynyl-phenanthroline spacer are described. Palladium(0) catalyses the coupling of the bis-ethynyl substituted central spacer with a bromo or a triflate functionalized bipyridine or terpyridine subunit. A novel trinuclear ruthenium

  描述了通过将两个三联吡啶或两个联吡啶与双取代的乙炔基联吡啶或双取代的乙炔基菲咯啉间隔基连接而获得的三位配体的合成和表征。钯（0）催化双乙炔基取代的中心间隔基与溴或三氟甲磺酸酯官能化联吡啶或三联吡啶亚基的偶联。还描述了新型三核钌（II）配合物。
• Construction of Preorganized Polytopic Ligands via Palladium-Promoted Cross-Coupling Reactions
  作者：Vincent Grosshenny、Francisco M. Romero、Raymond Ziessel

  DOI：10.1021/jo962068w

  日期：1997.3.1

  Rigid preorganized multitopic ligands have been designed and synthesized. The Pd(O)-catalyzed cross-coupling reactions between ethynylated derivatives of bipyridine or terpyridine and the corresponding bipyridine or terpyridine halides or triflates provide access to various homo-ditopic, hetero-ditopic, homo-tritopic, and hetero-tritopic ligands bearing acetylene or diphenylacetylene central units in fair to excellent yields. Optimal conditions mere found with [Pd(PPh(3))(2)Cl-2], CuI in THF and diisopropylamine at rt, or with [Pd(PPh(3))(4)] in benzene and diisopropylamine at 80 degrees C. When a phenylethynyl group is present in the molecule, the relevant conditions involve [Pd(PPh(3))(4)] in n-propylamine at 60 degrees C. Oxidative dimerization of the ethynylated derivatives in the presence of cupric salts and oxygen gives the corresponding homo-ditopic ligands bearing diacetylene or diphenyldiacetylene as a spacer in good yields. These methods provide a practical approach to the rational design of multichelating ligands for coordination of redox and photoactive transition metals.
• Romero, Francisco M.; Ziessel, Raymond; Dupont-Gervais, Annick, Journal of the Chemical Society. Chemical communications
  作者：Romero, Francisco M.、Ziessel, Raymond、Dupont-Gervais, Annick、Van Dorsselaer, Alain

  DOI：——

  日期：——