ethyl 3-(3,6-bis(dodecyloxy)-2,7-dimethoxyphenanthren-9-yl)-4-(4-(dodecyloxy)-3-methoxyphenyl)-1H-pyrrole-2-carboxylate | 1359741-27-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl 3-(3,6-bis(dodecyloxy)-2,7-dimethoxyphenanthren-9-yl)-4-(4-(dodecyloxy)-3-methoxyphenyl)-1H-pyrrole-2-carboxylate
• CAS: 1359741-27-7
• 化学式: C₆₆H₉₉NO₈
• 分子量: 1034.51
• InChiKey: LJWZLSYLIAJQEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.76
• 重原子数：
  75.0
• 可旋转键数：
  43.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  97.47
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-(3,6-bis(dodecyloxy)-2,7-dimethoxyphenanthren-9-yl)-4-(4-(dodecyloxy)-3-methoxyphenyl)-1H-pyrrole-2-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以98%的产率得到(3-(3,6-bis(dodecyloxy)-2,7-dimethoxyphenanthren-9-yl)-4-(4-(dodecyloxy)-3-methoxyphenyl)-1H-pyrrol-2-yl)methanol
  参考文献：
  名称：

  Peripherally Fused Porphyrins via the Scholl Reaction: Synthesis, Self-Assembly, and Mesomorphism

  摘要：

  Oxidative coupling of activated aryl groups attached to beta-positions of the porphyrin ring provides convenient access to derivatives containing peripherally fused phenanthrene and benzo[g]chrysene units. Tetra(benzochryseno)porphyrin, reported here for the first time, contains a nonplanar, sterically locked pi system and shows very intense electronic absorptions in the Q range of the electronic spectrum. Tetraphenanthroporphyrins show a tendency to aggregate in solution. In one case, a discrete dimer is formed, whose structure was investigated spectroscopically and theoretically. Derivatives bearing long alkyl chains are mesomorphic and exhibit columnar phases (tetraphenanthroporphyrins) and a monoclinic 3D phase (tetrabenzochrysenoporphyrin). The symmetry of column packing in the columnar phases is dependent on the number of alkyl chains per molecule. X-ray diffraction measurements show that, in spite of their nonplanarity, the aromatic cores in the mesophases are tightly stacked within the column. The corresponding stacking patterns were derived from the structure of the dimer, on the basis of geometrical analysis and molecular modeling.

  DOI：

  10.1021/ja210991f
• 作为产物：
  描述：

  癸基溴 在 sodium tetrahydroborate 、 氯化亚砜 、 potassium tert-butylate 、 sodium ethanolate 、 potassium carbonate 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 270.5h， 生成 ethyl 3-(3,6-bis(dodecyloxy)-2,7-dimethoxyphenanthren-9-yl)-4-(4-(dodecyloxy)-3-methoxyphenyl)-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Peripherally Fused Porphyrins via the Scholl Reaction: Synthesis, Self-Assembly, and Mesomorphism

  摘要：

  Oxidative coupling of activated aryl groups attached to beta-positions of the porphyrin ring provides convenient access to derivatives containing peripherally fused phenanthrene and benzo[g]chrysene units. Tetra(benzochryseno)porphyrin, reported here for the first time, contains a nonplanar, sterically locked pi system and shows very intense electronic absorptions in the Q range of the electronic spectrum. Tetraphenanthroporphyrins show a tendency to aggregate in solution. In one case, a discrete dimer is formed, whose structure was investigated spectroscopically and theoretically. Derivatives bearing long alkyl chains are mesomorphic and exhibit columnar phases (tetraphenanthroporphyrins) and a monoclinic 3D phase (tetrabenzochrysenoporphyrin). The symmetry of column packing in the columnar phases is dependent on the number of alkyl chains per molecule. X-ray diffraction measurements show that, in spite of their nonplanarity, the aromatic cores in the mesophases are tightly stacked within the column. The corresponding stacking patterns were derived from the structure of the dimer, on the basis of geometrical analysis and molecular modeling.

  DOI：

  10.1021/ja210991f