tetrakis>-strati-bis(5,10,15,20-tetraphenylporphyrin) | 133672-00-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: tetrakis>-strati-bis(5,10,15,20-tetraphenylporphyrin)
• 英文别名: tetrakis-strati-bis(5,10,15,20-tetraphenylporphyrin)；tetrakis[m,m-[(methylenecyanoimino)methylene]]-strati-bis(5,10,15,20-tetraphenylporphyrin)
• CAS: 133672-00-1
• 化学式: C₁₀₀H₆₈N₁₆
• 分子量: 1493.75
• InChiKey: MZDRHEGHVGJSDU-VDRGWZLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.83
• 重原子数：
  116.0
• 可旋转键数：
  0.0
• 环数：
  22.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  222.84
• 氢给体数：
  4.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  乙醇 、 tetrakis>-strati-bis(5,10,15,20-tetraphenylporphyrin) 在 三氟乙酸 作用下， 反应 72.0h， 生成 C₁₀₈H₉₂N₁₆O₄
  参考文献：
  名称：

  Symmetrical and unsymmetrical quadruply aza-bridged, closely interspaced, cofacial bis(5,10,15,20-tetraphenylporphyrin)s. 2. Synthesis, characterization, and conformational effects of solvents

  摘要：

  Several water- and non-water-soluble symmetrical and unsymmetrical quadruply aza bridged closely interspaced cofacial bis(5,10,15,20-tetraphenylporphyrin)s have been synthesized and fully characterized by 2D H-1-H-1 NMR (COSY), 2D C-13-H-1 NMR, FABMS, UV/vis, IR, and fluorescence spectral techniques. It was established, on the basis of H-1 NMR, UV/vis, and emission spectrophotometries, that tetrakis[m,m-(methylene(m-pyridinesulfonyl)imino)methylene]-strati-bis-(5,10,15,20-tetraphenylporphyrin) (5), tetrakis[m,m-(methylene(m-pyridiniumsulfonyl)imino)methylene]-strati-bis-(5,10,15,20-tetraphenylporphyrin) chloride (7), and tetrakis[m,m-(methylene(p-toluenesulfonyl)imino)methylene]-strati-bis(5,10,15,20-tetraphenylporphyrin) (11) exist in more than one conformation in DMSO and in only one symmetrical conformation in CHCl3. The biszinc and tetraprotonated 5, 7, and 11 exist in one conformation regardless of the solvent. These observations have been attributed to an interaction between DMSO and the pyrrolic N-H protons of the porphyrin cores which is inhibited by metalation (Zn2+) or protonation of the porphyrin moiety. Molecular dynamics calculations reveal that the intracavity interactions of 5 with DMSO are more important than the intercavity interactions which result in discrete, unsymmetrical conformations of the dimer. In contrast, tris[m,m-(methylene(m-pyridinesulfonyl)imino)methylene]-mono((((methylene-oxy)carbonyl)oxy)methylene-strati-bis(5,10,15,20-tetraphenylporphyrin) (6), tetrakis[m,m-(methylenecyanoimino)-methylene]-strati-bis(5,10,15,20-tetraphenylporphyrin) (8), tris[m,m-(methylenecyanoimino)methylene]-mono((((methyleneoxy)carbonyl)oxy)methylene)-strati-bis(5,10,15,20-tetraphenylporphyrin) (9), and tetrakis[m,m-(methylene(formamido)imino)methylene]-strati-bis(5,10,15,20-tetraphenylporphyrin) (10) do not show any conformational changes upon switching from chloroform to DMSO. This is attributed to the long interplanar distances calculated for the porphyrin dimers which prevent any intracavity coordination of DMSO with both porphyrin moieties. H-1 NMR variable-temperature experiments of porphyrin dimer 5 in DMSO show that the conformation of the dimer is greatly affected by temperature. While at room temperature 5 exists in more than one conformation, at higher temperatures (150-degrees-C) only one conformation is populated. It is proposed that at room temperature, the existence of a hydrogen-bonding network between DMSO and the dimer results in more than one conformation, while at higher temperatures the network is destroyed to furnish an average conformation.

  DOI：

  10.1021/ja00038a065
• 作为产物：
  描述：

  氰胺 、 5,10,15,20-tetrakis(3-(bromomethyl)phenyl)porphyrin 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以8%的产率得到tetrakis>-strati-bis(5,10,15,20-tetraphenylporphyrin)
  参考文献：
  名称：

  四重二原子和三原子、氮杂桥连、共面双（5,10,15,20-四苯基卟啉）的合成

  摘要：

  研究了四重氮杂桥接的共面双（5,10,15,20-四苯基卟啉）的几种合成方法。5,10,15,20-四 (α-溴-间-甲苯基) 卟啉 (2) 与对甲苯磺酰胺或氰胺和 Cs 2 CO 3 在二甲基甲酰胺中的高稀释度反应产生甲苯磺酰基和氰基二聚体 3a 和 3b 8% 的收益率。选择的方法是卟啉 2 与甲苯磺酰氨基卟啉 5a 在相同条件下反应，以 38% 的产率得到二聚体 3a。联苯自由基阴离子诱导的 3a 脱磺酰化提供了氨基二聚体 3c (41%)。卟啉 2 与甲苯磺酰氨基卟啉 13 的反应以 1% 的产率提供了二聚体 14（桥长度减少）。还讨论了合成 3a 和 3c 的其他方法。UV/vis 和 1 H NMR 光谱结果表明这些二聚体的“螺旋式”优选构象黯然失色，

  DOI：

  10.1021/ja00011a024

文献信息

• BOOKSER, BRETT C.;BRUICE, THOMAS C., J. AMER. CHEM. SOC., 113,(1991) N1, C. 4208-4218
  作者：BOOKSER, BRETT C.、BRUICE, THOMAS C.

  DOI：——

  日期：——