2,7-bis(2-pyridyloxy)naphthalene | 209663-43-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,7-bis(2-pyridyloxy)naphthalene
• 英文别名: 2,7-bis(pyridin-2-yloxy)naphthalene；2,2'-[naphthalene-2,7-diylbis(oxy)]dipyridine；2-(7-Pyridin-2-yloxynaphthalen-2-yl)oxypyridine；2-(7-pyridin-2-yloxynaphthalen-2-yl)oxypyridine
• CAS: 209663-43-4
• 化学式: C₂₀H₁₄N₂O₂
• 分子量: 314.343
• InChiKey: PEDLLPZQHFFVMV-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：

  2,7-bis(2-pyridyloxy)naphthalene 、 溴代十二烷 以 乙腈 为溶剂， 以70%的产率得到
  参考文献：
  名称：

  新型含萘-2,7-二基双(氧基)间隔基双吡啶鎓盐的合成及生物学评价

  摘要：

  DOI：

  10.1016/j.mencom.2020.11.004
• 作为产物：
  描述：

  2-溴吡啶 、 2,7-二羟基萘 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以30%的产率得到2,7-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

• Highly Regio- and Chemoselective Oxidative C–H/C–H Cross-Couplings of Anilines and Phenols Enabled by a Co-Oxidant-Free Rh(I)/Zn(NTf₂)₂/Air Catalytic System
  作者：Luoqiang Zhang、Yanbing Wang、Yang Shi、Yimin Wu、Jingbo Lan、Weixin Ma、Jingsong You

  DOI：10.1021/acscatal.9b00925

  日期：2019.6.7

  An urgent yet challenging task is to overcome the limitations in substrate scope and regio- and chemoselectivity in the oxidative couplings between two arenes for the construction of unsymmetrical 2,2′-difunctional biaryls with diverse application requirements. In this work, a co-oxidant-free Rh(I)/Zn(NTf2)2/air catalytic system has been developed for dual chelation-assisted oxidative C–H/C–H cross-couplings

  紧急而富挑战性的任务是克服底物范围以及两个芳烃之间氧化偶联中区域和化学选择性的局限性，以构建具有不同应用需求的不对称2,2'-双官能联芳基。在这项工作中，无助氧化剂的Rh（I）/ Zn（NTf 2）2/空气催化系统已经开发出来，可用于两个苯胺之间，两个苯酚之间以及苯酚和苯胺之间的双重螯合辅助氧化C–H / C–H交叉偶联，从而可以快速组装丰富的2,2'-库联苯胺，2,2'-联苯酚和2'-氨基联苯-2-醇。该方案以空气为唯一氧化剂，具有完全的区域选择性，高的化学选择性，低的底物摩尔比（甚至1：1），方便的操作和按比例放大的合成。既定的催化体系可耐受在芳基环的不同位置同时具有给电子和吸电子取代基的底物。这项工作进一步揭示了交叉偶联对同质偶联的化学选择性主要取决于两个导向基团（即，一对强和弱配位的导向基团，而不是两个底物之间的电子独特特性，这为设计用于双螯合辅助氧化Ar–H / Ar–H交叉偶联
• Chromium-Catalyzed Regioselective Kumada Arylative Cross-Coupling of C(aryl)–O Bonds with a Traceless Activation Strategy
  作者：Fei Fan、Jinghua Tang、Meiming Luo、Xiaoming Zeng

  DOI：10.1021/acs.joc.8b02104

  日期：2018.11.2

  We report here the chromium-catalyzed regioselective Kumada arylative cross-coupling of C(aryl)-O bonds at ambient temperature. By using a simple and low-cost chromium(II) chloride salt as a precatalyst, accompanied by a 2-pyridyl ligation, the catalytic cleavage and arylative coupling of C(aryl)-O bonds were achieved with a traceless activation strategy, overcoming the regioselectivity obstacle when several C-O bonds coexist in the Kumada coupling system.
• 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.