4'-(2,2'-bipyridin-4-ylethynyl)-2,2':6',2''-terpyridine | 146548-34-7

• 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: 4'-(2,2'-bipyridin-4-ylethynyl)-2,2':6',2''-terpyridine
• 英文别名: 2,6-Dipyridin-2-yl-4-[2-(2-pyridin-2-ylpyridin-4-yl)ethynyl]pyridine
• CAS: 146548-34-7
• 化学式: C₂₇H₁₇N₅
• 分子量: 411.465
• InChiKey: BCXHHKRTDYBIAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 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， 反应 22.0h， 生成 4'-(2,2'-bipyridin-4-ylethynyl)-2,2':6',2''-terpyridine
  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

• Synthesis and properties of novel ditopic polypyridine ligands bridged by one and two acetylenic bonds
  作者：Vincent Grosshenny、Raymond Ziessel

  DOI：10.1016/s0040-4039(00)74721-6

  日期：1992.12

  bipyridine or terpyridine subunits, in the presence of catalytic amounts of Pdo(PPh3)4 to yield, the new homo- and heteroditopic ethynyl bridge ligands 2a, 4a, 7a and 8. Self coupling of the ethynyl substituted bipyridine species in the presence of CuCl/TMEDA/O2, yield the symmetric diethynyl bridge ligands 2b, 4b and 7b.

  乙炔基取代的联吡啶螯合物与溴或三氟甲磺酸酯官能化联吡啶或三联吡啶亚基在催化量的Pd o（PPh 3）4存在下反应，生成新的均位和异位乙炔基桥配体2a，4a，7a和8。在CuCl / TMEDA / O 2存在下乙炔基取代联吡啶的自偶联产生对称的二乙炔基桥配体2b，4b和7b。