5,10,15,20-(tetra-2,6-difluorophenyl)porphyrin iron chloride | 221335-24-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 5,10,15,20-(tetra-2,6-difluorophenyl)porphyrin iron chloride
• 英文别名: chloro(tetrakis(2,6-difluorophenyl)porphyrinato)iron(III)；(5,10,15,20-tetrakis(2,6-difluorophenyl)porphyrinato)FeCl；tetrakis(2,6-difluororphenyl)porphinatoiron(III) chloride；[meso-5,10,15,20-tetrakis-(2,6-difluorophenyl)porhpyrinato]-iron(III) chloride；5,10,15,20-tetrakis(2,6-difluorophenyl)porphyrin iron(III) chloride；chloro(meso-tetrakis(2,6-difluorophenyl)porphirinato)iron(III)；iron(III) [tetrakis(2,6-difluorophenyl)]porphyrin chloride；iron(III) tetra(2,6-difluorophenyl)porphyrin chloride；[Fe(tetrakis(2,6-difluorophenyl)porphyrinate(2-))Cl]；(meso-tetrakis(2,6-difluorophenyl)porphinato(2-))Fe(III)Cl；(tetrakis(2,6-difluorophenyl)porphyrinate(2-))Fe(III)Cl；[Fe(tetrakis(o-difluorophenyl)porphyrin(2-))Cl]；(2,6-F8TPP)FeCl；F8TPPFe(III)Cl；[FeCl(tetrakis(2,6-difluorophenyl)porphyrinate(2-))]
• CAS: 221335-24-6
• 化学式: C₄₄H₂₀ClF₈FeN₄
• 分子量: 847.957
• InChiKey: KSEKXFHAGYLPEC-TXFZNMFQSA-M

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  5,10,15,20-(tetra-2,6-difluorophenyl)porphyrin iron chloride 在 HClO₄ 、 H₂O 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到[Fe(tetrakis(2,6-difluorophenyl)porphyrinate(2-))]2O
  参考文献：
  名称：

  X-ray Structure and Physical Properties of the Oxo-Bridged Complex [(F8-TPP)Fe-O-Cu(TMPA)]+, F8-TPP = Tetrakis(2,6-difluorophenyl)porphyrinate(2-), TMPA = Tris(2-pyridylmethyl)amine: Modeling the Cytochrome c Oxidase Fe-Cu Heterodinuclear Active Site

  摘要：

  The iron/copper heterodinuclear center in cytochrome c oxidases has attracted the interest of inorganic chemists since this is the site of dioxygen (O-2) four-electron four-proton reduction to water by the reduced enzyme, while the oxidized (''resting'') isolated protein dinuclear center exhibits unusual physical, spectroscopic, and ligand-binding properties. We describe here a model compound, [(F-8-TPP)Fe-III-O-Cu-II(TMPA)](+) (3), generated directly from O-2-reduction by 1:1 mixtures of the reduced copper(I) and iron(II) complexes [(TMPA)Cu-I(CH3CN)](+) (1) (TMPA = tris(2-pyridylmethyl)amine) and (F-8-TPP)Fe-II(pip)(2) (2) (F-8-TPP = tetrakis(2,6-difluorophenyl)porpyrinate-(2-), pip = piperidine) in O-2-saturated CH2Cl2 at -80 degrees C; warming to 0 degrees C, followed by precipitation with diethyl ether, affords 3 in similar to 70% yield, An X-ray diffraction study on [(F-8-TPP)Fe-O-Cu(TMPA)](ClO4).3C(7)H(8).2CH(3)CN (3-ClO4) as well as the mu-oxo iron dimer [(F-8-TPP)Fe]O-2.3C(7)H(8) allows for direct structural cc,mparisons, as well as with other relevant compounds. Compound 3 also possesses a linear mu-oxo-bridging ligand, where angle Fe-O-Cu = 178.2-(4)degrees; unusually short metal-oxygen distances of Fe-O = 1.740(5) Angstrom and Cu-O = 1.856(5) Angstrom are observed, and Fe...Cu = 3.596(2) Angstrom. The coordination geometry around Cu is distorted from the usual (i.e., for TMPA-Cu(II) complexes) trigonal-bipyramidal configuration toward a square-based pyramidal arrangement, and the three pyridine rings are situated between the four F-8-TPP phenyl rings, thus leaving one ''slot'' free. H-1-NMR spectra of 3-ClO4 in CD2Cl2 exhibit a pyrrole signal at 65 ppm (corroborated by H-2-NMR) which is upfield shifted relative to ol her axially symmetric high-spin (tetraphenylporphyrinate)iron(III) complexes; this is consistent with electronic/maegnetic coupling of the Fe(III) and Cu(II) centers. Additional upfield-shifted signals are tentatively assigned to the TMPA ligand on copper, thus implicating a bridged structural arrangement which is maintained in solution. A detailed magnetic Mossbauer spectroscopic study (4.2 K at 0, 0.5, and 8 T) has been carried out.The data unambiguously indicate that 3 possesses a high-spin ferric (S-Fe = 5/2) ion and exhibits characteristic parameters: D = 6.0 +/- 0.5 cm(-1) E/D = 0.03 +/- 0.01, Delta E(Q) = -1.26 +/- 0.02 mm/s, eta = 0, delta = 0.46 +/- 0.01 mm/s, and A/g(n) beta(n) = -23.7 +/- 0.3 T. Furthermore, the magnetic properties observed, i.e., in the presence or absence of an applied field, demonstrate that the ferric ion is spin-coupled to the cupric ion to form an overall integer spin system in [(F-8-TPP)(FeO)-O-III-Cu-II(TMPA)](ClO4) (3-ClO4). The Mossbauer isomer shift and quadrupole splitting parameters compare favorably with those previously obtained for data on enzyme resting-state preparations, although they differ in certain details. The conclusion that 3-ClO4 is an S = 2 system is determined by multifield saturation magnetization measurements, carried out both in solution (2-200 K) and the solid state (30-300 K). An exact magnetic coupling constant J (for exchange coupling according to (-2JS(1).S-2)) could not be determined from the solution data, due to the inherent ''noise'' found in these measurements, even for similar to 1 mM solutions. These findings carl into question previous evaluations for the lower limit of \J\ greater than or equal to 200 cm(-1) for the dinuclear Fe(III)-X-Cu(II) site in as-isolated ''resting'' oxidized cytochrome c oxidase enzyme; a lower limit of \J\ greater than 50 cm(-1) is suggested as a better estimate. Solid-state measurements on 3-ClO4 give a value of -J = 87 cm(-1), i.e., moderately strong antiferromagnetic coupling between high-spin iron(III) and copper(II) ions, consistent with the NMR and Mossbauer spectroscopic data. The possible biological relevance of the oxo-bridged complex [(F-8-TPP)Fe-III-O-Cu-II(TMPA)]ClO4) (3-ClO4) and its observed magnetic/electronic properties are discussed.

  DOI：

  10.1021/ja00090a023
• 作为产物：
  描述：

  5,10,15,20-tetrakis(2,6-difluorophenyl)porphyrin 在 iron(III) chloride hexahydrate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5,10,15,20-(tetra-2,6-difluorophenyl)porphyrin iron chloride
  参考文献：
  名称：

  Preparation of catalysts based on iron(III) porphyrins heterogenized on silica obtained by the Sol-Gel process for hydroxylation and epoxidation reactions

  摘要：

  Solid catalysts have been prepared by chemical interaction of iron(III) porphyrins with the surface of the pores of a silica matrix obtained by the sol-gel method. The presence of the complexes in the silica matrix and the morphology of the obtained particles were studied by UV-Vis spectroscopy, powder X-ray diffractometry, infrared spectroscopy, transmission electron microscopy, electron paramagnetic resonance and thermogravimetric analysis. The catalytic activity of the immobilized iron( III) porphyrins in the oxidation of (Z)-cyclooctene, cyclohexene and cyclohexane was evaluated in dichloromethane/ acetonitrile 1: 1 solvent mixture (v/v) using iodosylbenzene as oxidant. Results were compared with those achieved with the homogeneous counterparts.

  DOI：

  10.1590/s0103-50532010000700020
• 作为试剂：
  描述：

  异丁司特 在 sodium hypochlorite 、 5,10,15,20-(tetra-2,6-difluorophenyl)porphyrin iron chloride 、 十二烷基二甲基苄基氯化铵 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以65.4%的产率得到2-methyl-1-(10-propan-2-yl-3,6-dioxa-1,11-diazatetracyclo[6.3.0.02,4.05,7]undeca-8,10-dien-9-yl)propan-1-one
  参考文献：
  名称：