4,4'-(4,5-bis(dodecycloxy)-1,2-phenylene)-bis(2-methylbut-3-yn-2-ol) | 1066855-92-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4,4'-(4,5-bis(dodecycloxy)-1,2-phenylene)-bis(2-methylbut-3-yn-2-ol)
• 英文别名: 4-[4,5-Didodecoxy-2-(3-hydroxy-3-methylbut-1-ynyl)phenyl]-2-methylbut-3-yn-2-ol
• CAS: 1066855-92-2
• 化学式: C₄₀H₆₆O₄
• 分子量: 610.962
• InChiKey: UYQKRJPCJYTVKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.2
• 重原子数：
  44
• 可旋转键数：
  28
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,4'-(4,5-bis(dodecycloxy)-1,2-phenylene)-bis(2-methylbut-3-yn-2-ol) 在 氢氧化钾 、 盐酸 、 水 作用下， 以 甲苯 、 Petroleum ether 为溶剂， 反应 2.0h， 以95%的产率得到1,2-bis(dodecyloxy)-4,5-bis(ethynyl)benzene
  参考文献：
  名称：

  Folding a Conjugated Chain: Oligo(o-phenyleneethynylene-alt-p-phenyleneethynylene)

  摘要：

  An oligo(o-phenyleneethynylene-alt-p-phenyleneethynylene) was synthesized to create a conjugated molecule capable of adopting a helical secondary structure. A special feature of such a folded molecule is that the effective directions of energy/charge transport via covalent conjugation and through pi-pi stacking are converged to be along the helix axis. The transition from random conformations to the helix, driven by solvophobic and aromatic stacking interactions, was controlled by solvent properties. UV-vis and fluorescence spectroscopies gave supportive evidence for the folding process.

  DOI：

  10.1021/ol801677s
• 作为产物：
  描述：

  1,2-二(十二烷氧基)-4,5-二碘苯 、 2-甲基-3-丁炔-2-醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二异丙胺 作用下， 反应 3.0h， 以93%的产率得到4,4'-(4,5-bis(dodecycloxy)-1,2-phenylene)-bis(2-methylbut-3-yn-2-ol)
  参考文献：
  名称：

  Folding a Conjugated Chain: Oligo(o-phenyleneethynylene-alt-p-phenyleneethynylene)

  摘要：

  An oligo(o-phenyleneethynylene-alt-p-phenyleneethynylene) was synthesized to create a conjugated molecule capable of adopting a helical secondary structure. A special feature of such a folded molecule is that the effective directions of energy/charge transport via covalent conjugation and through pi-pi stacking are converged to be along the helix axis. The transition from random conformations to the helix, driven by solvophobic and aromatic stacking interactions, was controlled by solvent properties. UV-vis and fluorescence spectroscopies gave supportive evidence for the folding process.

  DOI：

  10.1021/ol801677s

文献信息

• Arylene Ethynylene Macrocycles with Intramolecular π−π Stacking
  作者：Shusen Chen、Qifan Yan、Tian Li、Dahui Zhao

  DOI：10.1021/ol101914f

  日期：2010.11.5

  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.