5-(2,3-dihydroxyphenyl)-10,15,20-tris(4-methylphenyl)porphyrin | 95998-85-9

• 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: 5-(2,3-dihydroxyphenyl)-10,15,20-tris(4-methylphenyl)porphyrin
• 英文别名: 5-(2,3-dihydroxyphenyl)-10,15,20-tri-p-tolylporphyrin
• CAS: 95998-85-9
• 化学式: C₄₇H₃₆N₄O₂
• 分子量: 688.828
• InChiKey: KDDSCEAJYMYGRI-KQWSROBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.66
• 重原子数：
  53.0
• 可旋转键数：
  4.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  97.82
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  7'-Apo-7'-(4-iodomethylphenyl)-β-carotene 、 5-(2,3-dihydroxyphenyl)-10,15,20-tris(4-methylphenyl)porphyrin 在 sodium methylate 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 0.5h， 以60%的产率得到carotenoporphyrin 9
  参考文献：
  名称：

  Stereodynamics of intramolecular triplet energy transfer in carotenoporphyrins

  摘要：

  DOI：

  10.1021/ja00298a038
• 作为产物：
  描述：

  5-(2,3-dimethoxyphenyl)-10,15,20-tris(4-methylphenyl)porphyrin 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 生成 5-(2,3-dihydroxyphenyl)-10,15,20-tris(4-methylphenyl)porphyrin
  参考文献：
  名称：

  Stereodynamics of intramolecular triplet energy transfer in carotenoporphyrins

  摘要：

  DOI：

  10.1021/ja00298a038

文献信息

• Covalently linked oxomolybdenum(V) and iron(III) porphyrin centers: Synthetic models for the molybdenum-iron interaction in sulfite oxidase
  作者：Partha Basu、Arnold M. Raitsimring、Michael J. LaBarre、Ish K. Dhawan、Jeff L. Weibrecht、John H. Enemark

  DOI：10.1021/ja00095a020

  日期：1994.8

  The modified tetraarylporphyrins 5-(3,4-dihydroxyphenyl)-10,15,20-tri-p-tolylporphyrin (3,4-OH-TTP, 3) and 5-(2,3-dihydroxyphenyl)-10,15,20-tri-p-tolylporphyrin (2,3-OH-TTP, 4) that possess a single pendant catechol group at one of the meso positions have been synthesized and used to investigate the coupling between oxo-Mo(V) and Fe(III) centers as preliminary models for the inter-prosthetic group interaction in sulfite oxidase. Reaction of these novel ligands with LMoO(2+) (L = hydrotris(3,5-dimethyl-1-pyrazolyl)borate) followed by insertion of Fe(III) into the porphyrin generates the bimetallic complexes FeCl(3,4-Mo-TTP) (11) and FeCl(2,3-Mo-TTP) (12) with controlled Mo...Fe distances of 9.4 and 7.3 Angstrom, respectively, as determined from computer modeling. Addition of excess N-methylimidazole (N-MeIm) produces the six-coordinate complexes Fe(N-MeIm)(2)(3,4-Mo-TTP)Cl (13) and Fe-(N-MeIm)(2)(2,3-Mo-TTP)Cl (14) with low-spin Fe(III) centers and two axial imidazole ligands. The formation constants for these bimetallic bis(N-methylimidazole) complexes are larger than those for related six-coordinated monometallic Fe(III) complexes of asymmetric porphyrin ligands. The interaction between the two S = 1/2 metal centers of Fe-(N-MeIm)(2)(3,4-Mo-TTP)Cl and Fe(N-MeIm)(2)(2,3-Mo-TTP)Cl has been probed by cyclic voltammetry and EPR spectroscopy. Simulation of the EPR spectra of these bimetallic Mo...Fe complexes shows that weak anisotropic dipolar coupling dominates the interaction between the two metals in Fe(N-MeIm)(2)(3,4-Mo-TTP)Cl (Mo...Fe similar to 9.4 Angstrom), whereas weak exchange interactions ((3-70) X 10(-3) cm(-1), 100-2000 MHz) predominate for Fe(N-MeIm)(2)(2,3-TTP)Cl (Mo...Fe similar to 7.9 Angstrom). The EPR simulations for both Fe(N-MeIm)(2)(3,4-Mo-TTP)Cl and Fe(N-MeIm)(2)(2,3-Mo-TTP)Cl require a distribution of coupling interaction energies, consistent with the presence of several rotamers of the N-methylimidazole ligand in solution that produce different orientations of the in-plane magnetic axes of the porphyrin. Cyclic voltammetry shows that two metal centers of Fe(N-MeIm)(2)(3,4-Mo-TTP)Cl and Fe(N-MeIm)(2)(2,3-Mo-TTP)Cl behave essentially as independent one-electron couples, but the potential of the Mo(V/IV) couple is sensitive to the electronic state and charge on the metalloporphyrin core.