5-(4-acetamidophenyl)-10,15,20-tris(4-methylphenyl)porphyrin | 57412-12-1

• 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: 5-(4-acetamidophenyl)-10,15,20-tris(4-methylphenyl)porphyrin
• 英文别名: 5-(4-acetamidophenyl)-10,15,20-tritolylporphyrin
• CAS: 57412-12-1
• 化学式: C₄₉H₃₉N₅O
• 分子量: 713.882
• InChiKey: NGJOCLZUOMICAR-VUXQGAMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.21
• 重原子数：
  55.0
• 可旋转键数：
  5.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  86.46
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-(4-acetamidophenyl)-10,15,20-tris(4-methylphenyl)porphyrin 在 盐酸 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 H-L-Asp(NH-H2TTP)-NH-p-tolyl
  参考文献：
  名称：

  β-转肽桥卟啉二聚体中的能量转移

  摘要：

  制备了 β-转肽桥联二卟啉化合物。每种异构的单锌配合物都很容易获得；无金属卟啉-肽-锌卟啉和锌卟啉-肽-无金属卟啉。在异构体中，从稳态荧光光谱分析，从锌卟啉部分到无金属卟啉部分的分子内能量转移效率是相同的，这表明效率应该独立于连接的肽间隔物并取决于它们之间的距离。分子中的卟啉部分。单线态能量可能主要通过空间机制从锌卟啉部分分子内迁移到不含金属的部分。

  DOI：

  10.1246/bcsj.66.3062
• 作为产物：
  描述：

  对甲基苯甲醛 在 三氟化硼乙醚 作用下， 以 氯仿 为溶剂， 反应 2.75h， 生成 5-(4-acetamidophenyl)-10,15,20-tris(4-methylphenyl)porphyrin
  参考文献：
  名称：

  带有碱性氨基的卟啉-希夫碱结合物作为抗微生物光疗剂

  摘要：

  通过含四吡咯大环的胺官能团和 4-(3-( N , N-二甲氨基)丙氧基)苯甲醛缩合合成了带有一 ( 6 ) 和两 ( 7 ) 个碱性氨基的新型卟啉-席夫碱共轭物。这种方法使我们能够在水性介质中轻松获得被正电荷前体基团取代的卟啉。这些化合物在N , N -二甲基甲酰胺中显示出典型的 Soret 和四个 Q 吸收带，具有红色荧光发射 (Φ F ~ 0.12) 。卟啉6和7对 O 2 ( 1 Δ g) (Φ Δ ~ 0.44) 和 L-色氨酸的光氧化。这种氨基酸的分解主要是由 II 型光过程介导的。此外，通过与 O 2 ( 1 Δ g ) 反应生成碘，KI 的加入强烈抑制了光动力作用。卟啉6和7诱导的光动力灭活能力在金黄色葡萄球菌、大肠杆菌和白色念珠菌中进行了评价。. 此外，这些微生物的光灭活使用碘阴离子增强作用得到改善。这些含有碱性脂肪族氨基的卟啉可以在生物系统中质子化，这为四吡咯大环提供了

  DOI：

  10.3390/molecules26195877

文献信息

• Synthesis of porphyrin dyads with potential use in solar energy conversion
  作者：Fernando Fungo、Luis A. Otero、Leonides Sereno、Juana J. Silber、Edgardo N. Durantini

  DOI：10.1039/a907428g

  日期：——

  A convenient procedure for the synthesis of porphyrin derivative dyads is described. The dyads consist of a free base porphyrin covalently linked to a zinc porphyrin or ferrocene by an amide bond. 5-(4-Substituted phenyl)-10,15,20-tris(4-methylphenyl) porphyrins were synthesized from meso-(4-methylphenyl) dipyrromethanes 1, which was obtained with appreciable yield (83%). The reaction of dipyrromethane 1 with a mixture of two appropriate substituted benzaldehydes affords the desired meso-substituted porphyrins, which can be easily separated by flash chromatography. These porphyrins bearing either one 4-acetamidophenyl group 2 or 4-carboxymethylphenyl group 3, and three 4-methylphenyl peripheral functional groups, were prepared with notable yields (15–17%) in a two-step one-flask reaction. Basic hydrolysis of the porphyrins 2 and 3 yielded amino 4 and acid porphyrin 5, respectively. Treatment of 5 with zinc acetate afforded the corresponding metal complex Zn-acid porphyrin 6. The dyads 7 and 8 were obtained by the coupling reaction between the acid chloride derivatives of either Zn-acid porphyrin 6 or ferroceneacetic acid and amino porphyrins 4, respectively. The present strategy may be easily used for preparation of other similar dyad derivatives. These compounds could have interesting applications in electronic materials. Preliminary studies of light energy conversion by SnO2 electrodes coated with porphyrin dyads 7 and 8 were performed. The results show that dyads 7 and 8 may be suitable for solar energy conversion devices.

  描述了一种合成卟啉衍生物二聚体的方便程序。该二聚体由一个自由基卟啉通过酰胺键与锌卟啉或铁烯连接。通过从中间体（4-甲基苯基）二吡咯烷1中合成出5-(4-取代苯基)-10,15,20-三(4-甲基苯基)卟啉，得到的产率可观（83%）。二吡咯烷1与两种适当取代的苯甲醛的混合物反应，能够获得所需的中间取代卟啉，这些产物可以通过闪光色谱法轻松分离。这些卟啉分别带有一个4-乙酰氨基苯基基团2或4-羧甲基苯基基团3，以及三个4-甲基苯基外围功能基团，采用两步一瓶反应法合成，得到的产率显著（15–17%）。对卟啉2和3的碱性水解反应分别生成氨基卟啉4和酸性卟啉5。将卟啉5与醋酸锌反应得到相应的金属复合物Zn-酸性卟啉6。通过酸氯化衍生物（Zn-酸性卟啉6或铁烯乙酸）与氨基卟啉4之间的耦合反应获得二聚体7和8。本策略可以轻松用于制备其他类似的二聚体衍生物。这些化合物在电子材料方面可能具有有趣的应用。对涂有卟啉二聚体7和8的SnO2电极进行的光能转换初步研究显示，二聚体7和8可能适用于太阳能转换设备。
• Synthesis of 5-(4-Acetamidophenyl)-10,15,20-<i>tris</i>(4-Substituted Phenyl) Porphyrins using Dipyrromethanes
  作者：Edgardo N. Durantini、Juana J. Silber

  DOI：10.1080/00397919908085963

  日期：1999.10

  A convenient procedure for the synthesis of 5-(4-acetamidophenyl)-10,15,20-tris(4-substituted phenyl) porphyrins (5-8) from dipyrromethane is reported. meso-(4-Substituted phenyl) dipyrromethanes (1-4) were obtained in yields of 72-84% by the reaction of 4-substituted benzaldehyde with an excess of pyrrole. The porphyrins (5-8) were isolated with appreciable yields of 15-17%.
• Gust, Devens; Moore, Thomas A.; Moore, Ana L., Journal of the American Chemical Society, 1991, vol. 113, # 10, p. 3638 - 3647
  作者：Gust, Devens、Moore, Thomas A.、Moore, Ana L.、Gao, Feng、Luttrull, David、DeGraziano, Janice M.、Ma, Xiaochun C.、Makings, Lewis R.、Lee, Seung-Joo、Trier, Todd T.、Bittersmann, Edith、Seely, Gilbert R.、Woodward, Susanne、Bensasson, René V.、Rougée, Michel、De Schryver, Frans C.、Van Der Auweraer, Mark

  DOI：——

  日期：——
• Photosensitization of Thin SnO₂ Nanocrystalline Semiconductor Film Electrodes with Metallodiporphyrin
  作者：Fernando Fungo、Luis Otero、Edgardo N. Durantini、Juana. J. Silber、Leonides E. Sereno

  DOI：10.1021/jp000140v

  日期：2000.8.1

  Sensitized photocurrent generation is observed with a porphyrin dyad (P-Zn-P) and its structural moieties: 5-(4-carboxyphenyl)-10,15,20-tris(4-methylphenyl) porphyrin (P) and Zn(II) 5-(4-carboxyphenyl)-10,15,20-tris(4-methylphenyl) porphyrin (P-Zn). The dyes were adsorbed to saturation on a nanocrystalline SnO2 thin film, employed as working electrode in a photoelectrochemical cell. The metallized and unmetallized moieties possess different singlet state energies and redox properties. In both, solution and adsorbed state, nearly complete singlet-singlet energy transfer from the P-Zn to P has been determined in the dyad. P-Zn is less efficient than P in the photocurrent generation, but is a suitable energy donor in the dyad molecule. The generation of photoelectrical effects by the dyad is less effective in comparison with P. Considering the oxidation potentials of the two moieties in P-Zn-P, a mechanism is proposed where the oxidized metallized porphyrin enhances the back electron-transfer process.
• Photophysical studies of tetratolylporphyrin photosensitizers for potential medical applications
  作者：Alina Dudkowiak、Ewa Teślak、Jan Habdas

  DOI：10.1016/j.molstruc.2005.12.052

  日期：2006.7

  A group of meso-substituted synthetic tetratolylporphyrins was investigated by the methods of absorption and fluorescence spectroscopies as well as steady-state and time-resolved photothermal spectroscopies. The experiments were carried out in the air, oxygen or nitrogen atmospheres, at two temperatures. The details concerning the fast and slow deactivation processes of excitation energy of the dyes were studied. The estimated quantum yield of fluorescence and the efficiency of (S-1-T-1) intersystem crossing process give a possibility to evaluate the population yield and quenching rate of the triplet state, important for the therapeutic application, mostly mediated by the T-1-state. For tetrapyrrole with the carboxyphenyl group substituted in meso-position, the triplet state yield was the highest, of 0.86-0.94, whereas the porphyrin with aminophenyl group seemed to be efficient singlet oxygen generators (0.81-0.99) with a high rate constant of its excited triplet state quenching by molecular oxygen. (c) 2006 Elsevier B.V. All rights reserved.