methyl 5-((5-tert-butyl-2-ethynylphenyl)ethynyl)picolinate | 1350553-51-3

• 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: methyl 5-((5-tert-butyl-2-ethynylphenyl)ethynyl)picolinate
• CAS: 1350553-51-3
• 化学式: C₂₁H₁₉NO₂
• 分子量: 317.387
• InChiKey: PBFSDZMFPKCKBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  39.19
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 5-((5-tert-butyl-2-ethynylphenyl)ethynyl)picolinate 在 吡啶 、 trans-bis(triphenylphosphine)palladium dichloride 、 碘 、 copper diacetate 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以64%的产率得到dimethyl 5,5'-(6,6'-(buta-1,3-diyne-1,4-diyl)bis(3-tert-butyl-6,1-phenylene)bis(ethyne-2,1-diyl))dipicolinate
  参考文献：
  名称：

  Fluorogenic N,O-chelates built on a C2-symmetric aryleneethynylene platform: Spectroscopic and structural consequences of conformational preorganization and ligand denticity

  摘要：

  Using p-extended aryleneethynylene as a rigid structural skeleton, a C-2-symmetric bis(picolinate) ligand was prepared. Binding of zinc(II) or cadmium(II) ion to this formally tetradentate N2O2-chelate resulted in significant red-shifts and enhancement in emission. The metal-ligand interaction responsible for such structural change was investigated by isolation and characterization of a tetrazinc(II) complex, in which the picolinate group functions not only as terminal bidentate but also as bridging with its mu-1,3 carboxylate unit. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2011.07.007
• 作为产物：
  描述：

  methyl 5-((5-tert-butyl-2-(trifluoromethylsulfonyloxy)phenyl)ethynyl)picolinate 在 copper(l) iodide 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 四丁基氟化铵 、 二异丙胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 methyl 5-((5-tert-butyl-2-ethynylphenyl)ethynyl)picolinate
  参考文献：
  名称：

  Fluorogenic N,O-chelates built on a C2-symmetric aryleneethynylene platform: Spectroscopic and structural consequences of conformational preorganization and ligand denticity

  摘要：

  Using p-extended aryleneethynylene as a rigid structural skeleton, a C-2-symmetric bis(picolinate) ligand was prepared. Binding of zinc(II) or cadmium(II) ion to this formally tetradentate N2O2-chelate resulted in significant red-shifts and enhancement in emission. The metal-ligand interaction responsible for such structural change was investigated by isolation and characterization of a tetrazinc(II) complex, in which the picolinate group functions not only as terminal bidentate but also as bridging with its mu-1,3 carboxylate unit. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2011.07.007