4-n-octyloxy-3,5-bis(pyridin-4-ylethynyl)benzaldehyde | 389069-11-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-n-octyloxy-3,5-bis(pyridin-4-ylethynyl)benzaldehyde
• 英文别名: 3,5-bis(4-pyridylethynyl)-4-octyloxybenzaldehyde；4-Octoxy-3,5-bis(2-pyridin-4-ylethynyl)benzaldehyde
• CAS: 389069-11-8
• 化学式: C₂₉H₂₈N₂O₂
• 分子量: 436.554
• InChiKey: ZGKDXKNCBGBOGB-UHFFFAOYSA-N

物化性质

• 沸点：
  652.6±55.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  吡咯 、 4-n-octyloxy-3,5-bis(pyridin-4-ylethynyl)benzaldehyde 在 丙酸 作用下， 反应 3.0h， 以9.9%的产率得到5,10,15,20-tetrakis[[3,5-bis(4-pyridyl)ethynyl-4-octyloxy]phenyl]porphyrin
  参考文献：
  名称：

  Construction of Monomeric and Polymeric Porphyrin Compartments by a Pd(II)−Pyridine Interaction and Their Chiral Twisting by a BINAP Ligand

  摘要：

  The construction of chirally twisted porphyrin-based molecular capsule 6 and polymeric capsule 8 was investigated by means of scanning electron microscopy (SEM) and H-1 NMR, LTV-visible, and CD spectroscopic observations. Molecular capsule 6 and polymeric capsule 8 were constructed by the reaction of chiral cis-Pd(II) complex 4 bearing a (R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) ligand with porphyrin 1 bearing four pyridyl groups and porphyrin 2 bearing eight pyridyl groups, respectively. The peak-splitting pattern of the beta-pyrrole protons in the 1H NMR spectrum and the specific CD spectral pattern bearing an exciton coupling band indicate that both molecular capsule 6 and polymeric capsule 8 are chirally twisted. Moreover, it was found that the CD intensity of the polymeric capsule plotted against [4]/([4] + [3]) shows a sigmoidal curvature, reflecting a unique cooperativity among the ligand groups; that is, the ligand existing in excess over the other dominates the twisting direction. These results consistently demonstrate that "chirality" in these molecular assembly systems is conveniently controlled by the use of chiral ligands.

  DOI：

  10.1021/jo020575+
• 作为产物：
  描述：

  1-碘辛烷 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 二异丙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 4-n-octyloxy-3,5-bis(pyridin-4-ylethynyl)benzaldehyde
  参考文献：
  名称：

  Construction of Monomeric and Polymeric Porphyrin Compartments by a Pd(II)−Pyridine Interaction and Their Chiral Twisting by a BINAP Ligand

  摘要：

  The construction of chirally twisted porphyrin-based molecular capsule 6 and polymeric capsule 8 was investigated by means of scanning electron microscopy (SEM) and H-1 NMR, LTV-visible, and CD spectroscopic observations. Molecular capsule 6 and polymeric capsule 8 were constructed by the reaction of chiral cis-Pd(II) complex 4 bearing a (R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) ligand with porphyrin 1 bearing four pyridyl groups and porphyrin 2 bearing eight pyridyl groups, respectively. The peak-splitting pattern of the beta-pyrrole protons in the 1H NMR spectrum and the specific CD spectral pattern bearing an exciton coupling band indicate that both molecular capsule 6 and polymeric capsule 8 are chirally twisted. Moreover, it was found that the CD intensity of the polymeric capsule plotted against [4]/([4] + [3]) shows a sigmoidal curvature, reflecting a unique cooperativity among the ligand groups; that is, the ligand existing in excess over the other dominates the twisting direction. These results consistently demonstrate that "chirality" in these molecular assembly systems is conveniently controlled by the use of chiral ligands.

  DOI：

  10.1021/jo020575+

文献信息

• A Novel Self-Assembled Porphyrin Polymer Constructed by a Pd(II)–Pyridine Interaction
  作者：Atsushi Ikeda、Masatsugu Ayabe、Seiji Shinkai

  DOI：10.1246/cl.2001.1138

  日期：2001.11

  A novel self-assembled polymer, which has a fibrous structure with enough long and many large inside cavities, was constructed by a pyridine–Pd(II) interaction from one mole of pyridine-containing porphyrin derivative and four moles of Pd(II) complex.

  一种新型自组装聚合物是由一摩尔含吡啶的卟啉衍生物和四摩尔钯（II）配合物通过吡啶-钯（II）相互作用构建而成的，这种聚合物具有足够长的纤维状结构和许多大的内腔。
• Construction of Monomeric and Polymeric Porphyrin Compartments by a Pd(II)−Pyridine Interaction and Their Chiral Twisting by a BINAP Ligand
  作者：Masatsugu Ayabe、Kousei Yamashita、Kazuki Sada、Seiji Shinkai、Atsushi Ikeda、Shigeru Sakamoto、Kentaro Yamaguchi

  DOI：10.1021/jo020575+

  日期：2003.2.1

  The construction of chirally twisted porphyrin-based molecular capsule 6 and polymeric capsule 8 was investigated by means of scanning electron microscopy (SEM) and H-1 NMR, LTV-visible, and CD spectroscopic observations. Molecular capsule 6 and polymeric capsule 8 were constructed by the reaction of chiral cis-Pd(II) complex 4 bearing a (R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) ligand with porphyrin 1 bearing four pyridyl groups and porphyrin 2 bearing eight pyridyl groups, respectively. The peak-splitting pattern of the beta-pyrrole protons in the 1H NMR spectrum and the specific CD spectral pattern bearing an exciton coupling band indicate that both molecular capsule 6 and polymeric capsule 8 are chirally twisted. Moreover, it was found that the CD intensity of the polymeric capsule plotted against [4]/([4] + [3]) shows a sigmoidal curvature, reflecting a unique cooperativity among the ligand groups; that is, the ligand existing in excess over the other dominates the twisting direction. These results consistently demonstrate that "chirality" in these molecular assembly systems is conveniently controlled by the use of chiral ligands.