5-ethynyl-5'-phenyl-2,2'-bipyridine | 1133486-44-8

• 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-ethynyl-5'-phenyl-2,2'-bipyridine
• 英文别名: 2-(5-Ethynylpyridin-2-yl)-5-phenylpyridine；2-(5-ethynylpyridin-2-yl)-5-phenylpyridine
• CAS: 1133486-44-8
• 化学式: C₁₈H₁₂N₂
• 分子量: 256.307
• InChiKey: QEGINFKWCRPURI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-3,3-二碘-2,2-双(甲氧基甲氧基)-1,1-联萘 、 5-ethynyl-5'-phenyl-2,2'-bipyridine 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 copper(l) iodide 、 1,1'-bis(diphenylphosphino)ferrocene 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 70.0h， 以91%的产率得到(M)-2,2'-di(methoxymethoxy)-3,3'-di(5-ethynediyl-5'-phenyl-2,2'-bipyridyl)-1,10-binaphthyl
  参考文献：
  名称：

  Surprising Substituent Effects on the Self-Assembly of Helicates from Bis(bipyridyl) BINOL Ligands

  摘要：

  A number of different bis(bipyridyl) BINOL ligands were prepared using a convergent building block approach, These were studied with regard to their ability to undergo self-assembly to dinuclear helicatcs upon coordination to suitable late-transition-metal ions. Surprisingly, the substituents at the periphery of the ligand structure were found to have a marked influence on the outcome of the self-assembly processes with regard to the helicates composition, the stereoselectivity of the helicate formation, their redox reactivity, and their electronical properties as scrutinized by NMR- and CD-spectroscopic methods as well as ESI-mass spectrometric methods.

  DOI：

  10.1021/jo900254r
• 作为产物：
  描述：

  5-phenyl-5'-[(trimethylsilyl)ethynyl]-2,2'-bipyridine 在 甲醇 、 potassium fluoride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以75%的产率得到5-ethynyl-5'-phenyl-2,2'-bipyridine
  参考文献：
  名称：

  Surprising Substituent Effects on the Self-Assembly of Helicates from Bis(bipyridyl) BINOL Ligands

  摘要：

  A number of different bis(bipyridyl) BINOL ligands were prepared using a convergent building block approach, These were studied with regard to their ability to undergo self-assembly to dinuclear helicatcs upon coordination to suitable late-transition-metal ions. Surprisingly, the substituents at the periphery of the ligand structure were found to have a marked influence on the outcome of the self-assembly processes with regard to the helicates composition, the stereoselectivity of the helicate formation, their redox reactivity, and their electronical properties as scrutinized by NMR- and CD-spectroscopic methods as well as ESI-mass spectrometric methods.

  DOI：

  10.1021/jo900254r

文献信息

• Bunzen, Jens; Bruhn, Torsten; Bringmann, Gerhard, Journal of the American Chemical Society, 2009, vol. 131, p. 3621 - 3630
  作者：Bunzen, Jens、Bruhn, Torsten、Bringmann, Gerhard、Luetzen, Arne

  DOI：——

  日期：——
• Surprising Substituent Effects on the Self-Assembly of Helicates from Bis(bipyridyl) BINOL Ligands
  作者：Jens Bunzen、Rainer Hovorka、Arne Lützen

  DOI：10.1021/jo900254r

  日期：2009.8.7

  A number of different bis(bipyridyl) BINOL ligands were prepared using a convergent building block approach, These were studied with regard to their ability to undergo self-assembly to dinuclear helicatcs upon coordination to suitable late-transition-metal ions. Surprisingly, the substituents at the periphery of the ligand structure were found to have a marked influence on the outcome of the self-assembly processes with regard to the helicates composition, the stereoselectivity of the helicate formation, their redox reactivity, and their electronical properties as scrutinized by NMR- and CD-spectroscopic methods as well as ESI-mass spectrometric methods.