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 | 1350553-54-6

• 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: 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
• 英文别名: Methyl 5-[2-[5-tert-butyl-2-[4-[4-tert-butyl-2-[2-(6-methoxycarbonylpyridin-3-yl)ethynyl]phenyl]buta-1,3-diynyl]phenyl]ethynyl]pyridine-2-carboxylate；methyl 5-[2-[5-tert-butyl-2-[4-[4-tert-butyl-2-[2-(6-methoxycarbonylpyridin-3-yl)ethynyl]phenyl]buta-1,3-diynyl]phenyl]ethynyl]pyridine-2-carboxylate
• CAS: 1350553-54-6
• 化学式: C₄₂H₃₆N₂O₄
• 分子量: 632.759
• InChiKey: WAGDBBVKDJDFOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  48
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  78.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  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 在 甲醇 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以70%的产率得到5,5'-(6,6'-(buta-1,3-diyne-1,4-diyl)bis(3-tert-butyl-6,1-phenylene)bis(ethyne-2,1-diyl))dipicolinic acid
  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：

  5-溴吡啶-2-羧酸甲酯 在 吡啶 、 potassium fluoride 、 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 、 trans-bis(triphenylphosphine)palladium dichloride 、 四丁基氟化铵 、 碘 、 copper diacetate 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 91.0h， 生成 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

文献信息

• Fluorogenic N,O-chelates built on a C2-symmetric aryleneethynylene platform: Spectroscopic and structural consequences of conformational preorganization and ligand denticity
  作者：Byung Gyu Park、Maren Pink、Dongwhan Lee

  DOI：10.1016/j.jorganchem.2011.07.007

  日期：2011.12

  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.