3-methoxy-4-n-octyloxy-5-pyridin-4-ylethynyl benzaldehyde | 500191-06-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-methoxy-4-n-octyloxy-5-pyridin-4-ylethynyl benzaldehyde
• 英文别名: 3-methoxy-4-octyloxy-5-(4-pyridylethynyl)benzaldehyde；3-Methoxy-4-octoxy-5-(2-pyridin-4-ylethynyl)benzaldehyde
• CAS: 500191-06-0
• 化学式: C₂₃H₂₇NO₃
• 分子量: 365.472
• InChiKey: RIXQHYADPPVVMX-UHFFFAOYSA-N

物化性质

• 沸点：
  543.7±50.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  吡咯 、 3-methoxy-4-n-octyloxy-5-pyridin-4-ylethynyl benzaldehyde 以 丙酸 为溶剂， 反应 3.0h， 以22%的产率得到tetrakis(3-(pyridine-4-ylethynyl)-4-octyloxy-5-methoxy)phenylporphyrin
  参考文献：
  名称：

  A Self-Assembled Porphyrin-Based Dimeric Capsule Constructed by a Pd(II)−Pyridine Interaction Which Shows Efficient Guest Inclusion

  摘要：

  [GRAPHICS]Novel self-assembled molecular capsules were constructed from two moles of pyridine-containing porphyrin derivatives and four moles of Pd(II) complexes utilizing a pyridine-Pd(ll) interaction. The H-1 NMR spectral studies established that these self assembled molecular capsules 5 and 6 have a highly symmetrical D-4h structure as well as a large inside cavity. It was shown that molecular capsule 6 can include a large bipyridine guest by a two point simultaneous pyridine-Zn(II) interaction.

  DOI：

  10.1021/ol006620m
• 作为产物：
  描述：

  5-碘香兰素 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 3-methoxy-4-n-octyloxy-5-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

• 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.
• A Self-Assembled Porphyrin-Based Dimeric Capsule Constructed by a Pd(II)−Pyridine Interaction Which Shows Efficient Guest Inclusion
  作者：Atsushi Ikeda、Masatsugu Ayabe、Seiji Shinkai、Shigeru Sakamoto、Kentaro Yamaguchi

  DOI：10.1021/ol006620m

  日期：2000.11.1

  [GRAPHICS]Novel self-assembled molecular capsules were constructed from two moles of pyridine-containing porphyrin derivatives and four moles of Pd(II) complexes utilizing a pyridine-Pd(ll) interaction. The H-1 NMR spectral studies established that these self assembled molecular capsules 5 and 6 have a highly symmetrical D-4h structure as well as a large inside cavity. It was shown that molecular capsule 6 can include a large bipyridine guest by a two point simultaneous pyridine-Zn(II) interaction.