2,6-bis(2-pyridyloxy)naphthalene | 509074-12-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-bis(2-pyridyloxy)naphthalene
• 英文别名: 2-(6-Pyridin-2-yloxynaphthalen-2-yl)oxypyridine；2-(6-pyridin-2-yloxynaphthalen-2-yl)oxypyridine
• CAS: 509074-12-8
• 化学式: C₂₀H₁₄N₂O₂
• 分子量: 314.343
• InChiKey: SPSZKVLEXKWRNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,6-bis(2-pyridyloxy)naphthalene 在 NEt₃ 作用下， 以 丙酮 、 苯 为溶剂， 生成 [((C5H4NO)2C10H4)Pd2(acac)2]*0.5H2O
  参考文献：
  名称：

  Cyclometalated Compounds. XVI.¹ Double Cyclopalladations of Bis(2-pyridyloxy)naphthalenes. Kinetic versus Thermodynamic Control of Regiospecificity

  摘要：

  A systematic study of the cyclopalladation reactions of bis(2-pyridyloxy)naphthalenes is described. On the basis of a kinetic preference for reaction at the 1-position, over thermodynamically favored reaction in the 3-position, a diverse range of doubly cyclopalladated compounds has been prepared, in a predictable manner, simply by moderating the experimental reaction conditions. Seven isomeric ligands have been employed to prepare many doubly metallated derivatives, all of which have been fully characterized by NMR spectroscopy, and two of which have been the subject of X-ray structure determinations. This study significantly expands the library of doubly cyclopalladated compounds, particularly those involving six-membered metallocycles.

  DOI：

  10.1021/om0207461
• 作为产物：
  描述：

  2-溴吡啶 、 2,6-萘二酚 在 potassium carbonate 作用下， 以 环丁砜 、 甲苯 为溶剂， 反应 40.0h， 以75%的产率得到2,6-bis(2-pyridyloxy)naphthalene
  参考文献：
  名称：

  Synthesis and Characterisation of Eight Isomeric Bis(2-pyridyloxy)naphthalenes

  摘要：

  八种异构体双(2-吡啶氧)萘已通过2-溴吡啶与适当的二羟基萘反应制备，并通过1D和2D核磁共振光谱法对产物进行了充分表征。

  DOI：

  10.3390/11090684

文献信息

• Synthesis and Characterisation of Eight Isomeric Bis(2-pyridyloxy)naphthalenes
  作者：Brendan O’Keefe、Peter Steel

  DOI：10.3390/11090684

  日期：——

  Eight isomeric bis(2-pyridyloxy)naphthalenes have been prepared from reactions of 2-bromopyridine with the appropriate dihydroxynaphthalene and the products fully characterised by 1- and 2-D NMR spectroscopy.

  八种异构体双(2-吡啶氧)萘已通过2-溴吡啶与适当的二羟基萘反应制备，并通过1D和2D核磁共振光谱法对产物进行了充分表征。
• Cyclometalated Compounds. XVI.¹ Double Cyclopalladations of Bis(2-pyridyloxy)naphthalenes. Kinetic versus Thermodynamic Control of Regiospecificity
  作者：Brendan J. O'Keef、Peter J. Steel

  DOI：10.1021/om0207461

  日期：2003.3.1

  A systematic study of the cyclopalladation reactions of bis(2-pyridyloxy)naphthalenes is described. On the basis of a kinetic preference for reaction at the 1-position, over thermodynamically favored reaction in the 3-position, a diverse range of doubly cyclopalladated compounds has been prepared, in a predictable manner, simply by moderating the experimental reaction conditions. Seven isomeric ligands have been employed to prepare many doubly metallated derivatives, all of which have been fully characterized by NMR spectroscopy, and two of which have been the subject of X-ray structure determinations. This study significantly expands the library of doubly cyclopalladated compounds, particularly those involving six-membered metallocycles.