5,15-Bis(4-pyridyl)-2,8,12,18-tetraethyl-3,7,13,17-tetramethylporphyrin | 123747-40-0

• 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: 5,15-Bis(4-pyridyl)-2,8,12,18-tetraethyl-3,7,13,17-tetramethylporphyrin
• CAS: 123747-40-0
• 化学式: C₄₂H₄₄N₆
• 分子量: 632.852
• InChiKey: NMQHJGSPVYSPSY-SJRNHBOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.86
• 重原子数：
  48.0
• 可旋转键数：
  6.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  83.14
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5,15-Bis(4-pyridyl)-2,8,12,18-tetraethyl-3,7,13,17-tetramethylporphyrin 、 碘甲烷 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 5,15-Bis(4-N-methylpyridiniumiodide)-2,8,12,18-tetraethyl-3,7,13,17-tetramethylporphyrin
  参考文献：
  名称：

  关于5-（4-烷氧基苯基）-15-（4-吡啶基）卟啉的甲基化

  摘要：

  在酸性介质中将3,3'-二乙基-4,4'-二甲基-2,2'-二吡咯基甲烷1与4-甲酰基吡啶2和4-烷氧基苯甲醛3混合缩合，然后将反应混合物与DDQ氧化，得到其他化合物，标题化合物5。描述了5-（4-烷氧基苯基）-15-（4-吡啶基）卟啉中吡啶基的有效甲基化方法。1与N-甲基-4-甲酰基吡啶鎓盐9和3的混合缩合反应可得到其他化合物5-（4- N-甲基吡啶并氨基吡啶鎓）卟啉10。

  DOI：

  10.1002/jhet.5570270641
• 作为产物：
  描述：

  4-吡啶甲醛 、 3-ethyl-2-[(3-ethyl-4,5-dimethyl-1H-pyrrol-2-yl)methyl]-4,5-dimethyl-1H-pyrrole 在 四氯苯醌 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以10.5%的产率得到5,15-Bis(4-pyridyl)-2,8,12,18-tetraethyl-3,7,13,17-tetramethylporphyrin
  参考文献：
  名称：

  Peripheral substituents of di(pyridiumyl)porphyrins affected on their interactions with DNA

  摘要：

  meso- and beta-Substituted di(pyridiumyl)porphyrins 3, 4, and 7 have been synthesized and their interactions with DNA have been investigated. meso- Substituted porphyrins showed the stronger effect on DNA than that of beta-substituted porphyrin. Cytoxicity of compound 3 (IC50) to THP-1 tumor cell was up to 0.11 nM. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.083

文献信息

• Thermodynamics of induced-fit binding inside polymacrocyclic porphyrin hosts
  作者：Harry L. Anderson、Christopher A. Hunter、M. Nafees Meah、Jeremy K. M. Sanders

  DOI：10.1021/ja00171a017

  日期：1990.7

  The binding of bis-amine ligands to a series of cyclic zinc porphyrin dimers has been characterized by NMR and electronic spectroscopy. The cavity within the flexible dimers is kept closed by pi}-pi} interactions between the porphyrin and aromatic bridging groups but can be opened by ligands whose binding is strong enough to overcome this energetic barrier. Analysis of the binding of these bifunctional

  双胺配体与一系列环状锌卟啉二聚体的结合已通过核磁共振和电子光谱表征。柔性二聚体内的空腔通过卟啉和芳族桥接基团之间的 pi}-pi} 相互作用保持关闭，但可以通过结合强度足以克服这种能量障碍的配体打开。对这些双功能和相应的单功能配体与卟啉二聚体和相应单体卟啉的结合的分析允许定义参数Delta}Delta}G、Delta}Delta}H和Delta}Delta}S。这些与构象转换的能量成本特别相关，并产生关于保持腔关闭的 pi}-pi} 相互作用强度的信息。
• Electrochemical behavior of a number of bispyridyl-substituted porphyrins and their electrocatalytic activity in molecular oxygen reduction reaction
  作者：Minh N. Do、Nadezhda M. Berezina、Mikhail I. Bazanov、Sabir S. Gyseinov、Mikhail M. Berezin、Oscar I. Koifman

  DOI：10.1142/s1088424616500437

  日期：2016.5

  18-tetraethylporphinato]cobalt(II) and bispyridine[5,15-bis(pyrid-4-yl)-3,7,13,17-tetramethyl-2,8,12,18-tetraethylporphinato]cobalt(III) in 0.1 M KOH aqueous solution has been carried out by cyclic voltammetry. The potential ranges of redox processes related to the transformation of the porphyrin macrocycle, pyridyl substituents and central metal have been established. The electrochemical parameters of oxygen electroreduction

  5,15-bis(pyrid-3-yl)-3,7,13,17-tetramethyl-2,8,12,18-tetraethylporphine, [5,15-bis(pyrid) 活性层电化学性能的研究-3-yl)-3,7,13,17-tetramethyl-2,8,12, 18-tetraethylporphinato]cobalt(II), 双吡啶[5,15-bis(pyrid-3-yl)-3,7, 13,17-tetramethyl-2,8,12,18-tetraethylporphinato]cobalt(III), [5,15-bis(pyrid-4-yl)-3,7,13,17-tetramethyl-2,8,12 ,18-四乙基卟啉基]钴(II)和双吡啶[5,15-双(吡啶-4-基)-3,7,13,17-四甲基-2,8,12,18-四乙基卟啉基]钴(III) 0.1 M KOH
• Pyridyl-substituted porphyrins: II. Synthesis and basic properties of dipyridylporphyrins
  作者：Yu. B. Ivanova、A. S. Semeikin、A. V. Glazunov、N. Zh. Mamardashvili

  DOI：10.1134/s1070428010060230

  日期：2010.6

  18-tetraethylporphyrins were synthesized, and their acid-base properties in ethanol-sulfuric acid were studied by spectrophotometric titration. Concentration ranges for the existence of mono- and dicationic forms of 5,15-dipyridylporphyrins and the corresponding ionization constants were determined. The effect of pyridine fragments on the basic properties of alkyl-substituted porphyrins was discussed.

  5,15-双（吡啶-2-基）-，5,15-双（吡啶-3-基）-和5,15-双（吡啶-4-基）-取代的3,7,13,17合成了-tetramethyl-2,8,12,18-tetraethylporphyrins，并通过分光光度滴定法研究了它们在乙醇-硫酸中的酸碱性质。确定了5,15-二吡啶基卟啉单价和双价形式存在的浓度范围以及相应的电离常数。讨论了吡啶片段对烷基取代卟啉基本性质的影响。
• Assembly of a photoactive supramolecule using porphyrin co-ordination chemistry
  作者：Harry L. Anderson、Christopher A. Hunter、Jeremy K. M. Sanders

  DOI：10.1039/c39890000226

  日期：——

  A bis(4-pyridyl)-porphyrin has been synthesised and shown to bind within the cavity of a host metalloporphyrin–pyromellitimide dimer; fluorescence quenching of the bound guest implies a photoinduced electron transfer to the pyromellitimide moieties of the host molecule.

  已经合成了双（4-吡啶基）-卟啉，并显示其结合在宿主金属卟啉-均苯四甲酰亚胺二聚体的腔内；结合的客体的荧光猝灭意味着光诱导的电子转移到宿主分子的均苯四甲酰亚胺部分。
• Dicationic pyridium porphyrins appending different peripheral substituents: Synthesis and studies for their interactions with DNA
  作者：Song Wu、Zheng Li、Lige Ren、Bo Chen、Feng Liang、Xiang Zhou、Tao Jia、Xiaoping Cao

  DOI：10.1016/j.bmc.2005.12.011

  日期：2006.5

  Twelve trans-dicationic pyridium porphyrins appending different peripheral substituents were synthesized and their abilities to bind and cleave DNA under irradiation have been investigated. Their binding modes to DNA were studied by UV-vis spectroscopy, circular dichroism. The apparent constants were measured by EB competitive fluorescence method and most of them were in the range of 10(4) - 10(5) M-1. We found that both the position of positive charges and steric hindrance Could greatly influence their binding affinities and modes to DNA, and then affect their photocleaving abilities to DNA. (c) 2005 Elsevier Ltd. All rights reserved.