5,10,15,20-tetrakis(2,6-difluorophenyl)porphyrin | 104322-39-6

• 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: 5,10,15,20-tetrakis(2,6-difluorophenyl)porphyrin
• 英文别名: 5,10,15,20-tetra(2,6-difluorophenyl)porphyrin；tetrakis(2,6-difluorophenyl)porphyrin；tetra(2,6-difluorophenyl) porphyrin
• CAS: 104322-39-6
• 化学式: C₄₄H₂₂F₈N₄
• 分子量: 758.673
• InChiKey: XQZSSXGRTAZHLI-DSIMAETFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.44
• 重原子数：
  56.0
• 可旋转键数：
  4.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.36
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2,6-二氟苯甲醛 在 三氟化硼乙醚 四氯苯醌 作用下， 以 氯仿 为溶剂， 反应 2.0h， 生成 5,10,15,20-tetrakis(2,6-difluorophenyl)porphyrin
  参考文献：
  名称：

  Investigation of the synthesis of ortho-substituted tetraphenylporphyrins

  摘要：

  DOI：

  10.1021/jo00265a021

文献信息

• Arylruthenium(III) Porphyrin-Catalyzed C–H Oxidation and Epoxidation at Room Temperature and [Ru^V(Por)(O)(Ph)] Intermediate by Spectroscopic Analysis and Density Functional Theory Calculations
  作者：Ka-Pan Shing、Bei Cao、Yungen Liu、Hung Kay Lee、Ming-De Li、David Lee Phillips、Xiao-Yong Chang、Chi-Ming Che

  DOI：10.1021/jacs.8b04470

  日期：2018.6.6

  metal catalysts for efficient oxidation of hydrocarbons and identification of the reactive intermediates in the oxidation catalysis are long-standing challenges. In the rapid hydrocarbon oxidation catalyzed by ruthenium(IV) and -(III) porphyrins, the putative Ru(V)-oxo intermediates remain elusive. Herein we report that arylruthenium(III) porphyrins are highly active catalysts for hydrocarbon oxidation

  开发用于烃类有效氧化的高活性和选择性金属催化剂以及氧化催化中反应中间体的鉴定是长期存在的挑战。在钌 (IV) 和 -(III) 卟啉催化的快速烃氧化中，推定的 Ru(V)-氧代中间体仍然难以捉摸。在此我们报告芳基钌 (III) 卟啉是烃氧化的高活性催化剂。使用催化剂 [RuIII(TDCPP)(Ph)(OEt2)] (H2TDCPP = 5,10,15,20-四(2,6-二氯苯基)卟啉)，在氧化剂 m-CPBA 下氧化各种碳氢化合物的 CH 键室温下，醇/酮在 1 小时内的收率高达 99%；使用 [ nBu4N]IO4 作为温和的替代氧化剂避免了 CH 氧化中环酮形成内酯，催化环氧化反应在 5 分钟内完成，收率高达 99%，选择性高（无醛类副产物）。UV-vis、电喷雾电离质谱、共振拉曼、电子顺磁共振、动力学测量和密度泛函理论计算为 Ru(V)-氧代中间体 [RuV(TDCPP)(O)(Ph)]
• Biologically Inspired and Magnetically Recoverable Copper Porphyrinic Catalysts: A Greener Approach for Oxidation of Hydrocarbons with Molecular Oxygen
  作者：César A. Henriques、Auguste Fernandes、Liane M. Rossi、M. Filipa Ribeiro、Mário J. F. Calvete、Mariette M. Pereira

  DOI：10.1002/adfm.201505405

  日期：2016.5

  hybrid copper porphyrinic nanomaterials is reported. These functionalized magnetic materials prove to be efficient bioinspired oxidation catalysts of olefins and thiols, using molecular oxygen as oxidant, in total absence of reductants and solvents, with the highest TON (turnover number) yet achieved for this reaction (≈200 000). A comparative study between homogeneous and heterogeneous oxidation of cyclohexene

  报道了一种可磁回收杂化铜卟啉纳米材料的有效合成方法。这些功能化的磁性材料被证明是有效的烯烃和硫醇的生物启发性氧化催化剂，使用分子氧作为氧化剂，完全不存在还原剂和溶剂，该反应的TON（周转数）最高（≈200000）。讨论了环己烯均相和非均相氧化的比较研究，发现该非均相体系在催化剂的稳定性和可重复使用性方面是最有前途的。通过透射电子显微镜，火焰原子吸收光谱法，热重分析法，N 2表征杂化卟啉纳米材料的磁性 还描述了吸附和红外光谱。
• Symmetric and Asymmetric Halogen-Containing Metallocarboranylporphyrins and Uses Thereof
  申请人：Miura Michiko

  公开号：US20080233047A1

  公开（公告）日：2008-09-25

  The present invention is directed to low toxicity boronated compounds and methods for their use in the treatment, visualization, and diagnosis of tumors. More specifically, the present invention is directed to low toxicity halogenated, carborane-containing 5,10,15,20-tetraphenylporphyrin compounds and methods for their use particularly in boron neutron capture therapy (BNCT) and photodynamic therapy (PDT) for the treatment of tumors of the brain, head and neck, and surrounding tissue. The invention is also directed to using these halogenated, carborane-containing tetraphenylporphyrin compounds in methods of tumor imaging and/or diagnosis such as MRI, SPECT, or PET.

  本发明涉及低毒性硼化合物及其在肿瘤治疗、可视化和诊断中的应用方法。更具体地说，本发明涉及低毒性卤代、含碳硼烷的5,10,15,20-四苯基卟啉化合物及其在硼中子俘获治疗（BNCT）和光动力疗法（PDT）中的应用方法，特别用于治疗脑部、头颈部和周围组织的肿瘤。该发明还涉及将这些卤代、含碳硼烷的四苯基卟啉化合物用于肿瘤成像和/或诊断的方法，例如MRI、SPECT或PET。
• Halogenated meso-phenyl Mn(III) porphyrins as highly efficient catalysts for the synthesis of polycarbonates and cyclic carbonates using carbon dioxide and epoxides
  作者：Laia Cuesta-Aluja、Javier Castilla、Anna M. Masdeu-Bultó、César A. Henriques、Mário J.F. Calvete、Mariette M. Pereira

  DOI：10.1016/j.molcata.2015.10.025

  日期：2016.11

  ortho position of the aryl groups of meso -tetraphenylporphyrin manganese(III) complexes increased their activity as catalysts in the reaction of carbon dioxide with epoxides, when compared with the meso -tetraphenylporphyrin manganese(III) counterpart, even in the absence of co-catalysts. In the polymerization reaction of carbon dioxide and cyclohexene oxide, almost ten-fold increase of the TOF was

  摘要 与内消旋四苯基卟啉相比，在内消旋四苯基卟啉锰（III）配合物芳基邻位引入卤素吸电子原子（氯和氟）可提高其作为二氧化碳与环氧化物反应催化剂的活性。锰（III）对应物，即使在没有助催化剂的情况下。在二氧化碳和氧化环己烯的聚合反应中，当 5,10,15,20-四（2,6-二氯苯基）卟啉锰（III）乙酸酯或 5,10,15， 20-四(2,6-二氟苯基)卟啉锰(III)乙酸盐配合物用作催化剂。在类似条件下，当末端环氧化物用作底物时，CO 2 与氧化苯乙烯、环氧氯丙烷、环氧丙烷和 1 的选择性环加成反应，
• Ecofriendly Porphyrin Synthesis by using Water under Microwave Irradiation
  作者：César A. Henriques、Sara M. A. Pinto、Gilberto L. B. Aquino、M. Pineiro、Mário J. F. Calvete、Mariette M. Pereira

  DOI：10.1002/cssc.201402464

  日期：2014.10

  Water, under microwave irradiation and at a temperature of 473 K, reaches pressures above 16 bar, being capable to act as catalyst, without the use of organic solvents and oxidants, for meso‐substituted porphyrin synthesis. Sustainability of the reaction is proved by E Factor=35 and EcoScale value of 50.5, the highest so far obtained for porphyrin synthesis. Methodology’s wide versatility is clearly

  在微波辐射下和温度为473 K的情况下，水达到16 bar以上的压力，能够在不使用有机溶剂和氧化剂的情况下充当催化剂，用于介孔取代的卟啉合成。该反应的可持续性由E因子= 35和EcoScale值为50.5证明，这是迄今为止卟啉合成所获得的最高值。芳基和烷基取代的卟啉均获得了良好的收率，这清楚地证明了该方法学的广泛用途。这些反应条件代表着巨大的发展，不仅通过使用非常高的浓度，最大程度地减少有机溶剂的使用，而且还通过消除有毒的昂贵溶剂和氧化剂。