4,4'-((naphthalene-1,4-diylbis(ethyne-2,1-diyl))bis(4,5-bis(dodecyloxy)-2,1-phenylene))bis(2-methylbut-3-yn-2-ol) | 1253228-23-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4,4'-((naphthalene-1,4-diylbis(ethyne-2,1-diyl))bis(4,5-bis(dodecyloxy)-2,1-phenylene))bis(2-methylbut-3-yn-2-ol)
• CAS: 1253228-23-7
• 化学式: C₈₄H₁₂₄O₆
• 分子量: 1229.9
• InChiKey: AXWXSMSYYDCKBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  23.08
• 重原子数：
  90.0
• 可旋转键数：
  48.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4,4'-((naphthalene-1,4-diylbis(ethyne-2,1-diyl))bis(4,5-bis(dodecyloxy)-2,1-phenylene))bis(2-methylbut-3-yn-2-ol) 在 potassium carbonate 、 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以89%的产率得到
  参考文献：
  名称：

  Arylene Ethynylene Macrocycles with Intramolecular π−π Stacking

  摘要：

  Arylene ethynylene macrocycles containing 9,10-anthrylene or 1,4-naphthylene units were synthesized. In chloroform, significant resonance upfield shifting was observed with beta-protons of anthrylene and naphthylene in NMR spectra. This was considered to result from partial stacking of these aromatic units intramolecularly, driven by attractive pi-pi interactions. DFT calculations supported the proposed intramolecular stacking motif. Moreover, a liquid-crystal phase was exhibited by the anthrylene-containing macrocycle, by virtue of the unique discotic shape.

  DOI：

  10.1021/ol101914f
• 作为产物：
  描述：

  1,4-二溴代萘 、 4-(4,5-bis(dodecycloxy)-2-ethynylphenyl)-2-methylbut-3-yn-2-ol 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以65%的产率得到4,4'-((naphthalene-1,4-diylbis(ethyne-2,1-diyl))bis(4,5-bis(dodecyloxy)-2,1-phenylene))bis(2-methylbut-3-yn-2-ol)
  参考文献：
  名称：

  Arylene Ethynylene Macrocycles with Intramolecular π−π Stacking

  摘要：

  Arylene ethynylene macrocycles containing 9,10-anthrylene or 1,4-naphthylene units were synthesized. In chloroform, significant resonance upfield shifting was observed with beta-protons of anthrylene and naphthylene in NMR spectra. This was considered to result from partial stacking of these aromatic units intramolecularly, driven by attractive pi-pi interactions. DFT calculations supported the proposed intramolecular stacking motif. Moreover, a liquid-crystal phase was exhibited by the anthrylene-containing macrocycle, by virtue of the unique discotic shape.

  DOI：

  10.1021/ol101914f