5-(4-乙酰氨基苯基)-10,15,20-三(苯基)卟啉 | 126442-89-5

• 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
• 中文名称: 5-(4-乙酰氨基苯基)-10,15,20-三(苯基)卟啉
• 英文名称: 5-(4-acetamidophenyl)-10,15,20-triphenylporphyrin
• 英文别名: 5-(4-acetamidophenyl)-10,15,20-tris(phenyl)porphyrin；5,10,15-triphenyl-20-(4-acetamidophenyl)porphyrin
• CAS: 126442-89-5
• 化学式: C₄₆H₃₃N₅O
• 分子量: 671.801
• InChiKey: FREJVQOCIVTKID-CRLDETFASA-N

物化性质

• 熔点：
  >300 °C (decomp)(Solv: methanol (67-56-1))
• 密度：
  1.283±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.28
• 重原子数：
  52.0
• 可旋转键数：
  5.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.02
• 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-乙酰氨基苯基)-10,15,20-三(苯基)卟啉 在 盐酸 、 三氟乙酸 作用下， 反应 21.0h， 以77%的产率得到5-(p-aminophenyl)-10,15,20-triphenylporphine
  参考文献：
  名称：

  共价连接的卟啉-花青染料的可见光收集

  摘要：

  我们报告了新型的光化学模型化合物的三个成员的合成和性质，这些化合物包含共价连接的卟啉和花菁染料。在化合物1和2中，染料在450-570 nm范围内吸收，并且从染料到游离碱卟啉的能量转移效率为80％。在化合物3中，染料在650-780 nm范围内吸收，从游离碱卟啉到染料的能量转移效率为80％。锌卟啉染料表现出给体和受体猝灭，只有中等程度的能量转移。这项工作是迈向人工藻胆体发展的第一步。

  DOI：

  10.1016/s0040-4020(01)85156-5
• 作为产物：
  描述：

  在 四氯苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以1.1 g的产率得到5-(4-乙酰氨基苯基)-10,15,20-三(苯基)卟啉
  参考文献：
  名称：

  Design of novel luminescent porphyrins bearing donor–acceptor groups

  摘要：

  在这项工作中，我们报告了一系列新型卟啉的合成和特性，其中一些卟啉带有供体-受体基团。中取代游离基卟啉：我们合成并表征了 5-(4-氨基苯基)-10,15,20-三苯基卟啉（TPPNH2）和 5-(4-乙酰氨基苯基)-10,15,20-三苯基卟啉（TPPNHAc）及其三溴卟啉（Br3TPPNH2 和 Br3TPPNHAc）和三甲基硅取代的同系物（TMS3TPPNH2 和 TMS3TPPNHAc）。通过吸收光谱和荧光光谱研究了所有化合物的光学性质。为了确定优化的几何形状以及与光学特性的相关性，还进行了理论计算。另一方面，还制备了一种含偶氮苯的卟啉（TPPN2PhC14H29），以研究反式-顺式光异构化对其光学性质的影响。几乎所有的卟啉衍生物都在约λ = 419-422 nm处显示出一个索雷特波段，随后在500-700 nm范围内显示出四个Q波段。此外，根据取代基的不同，这些卟啉还显示出两个强度不同的发射带，分别位于约 λ = 654 纳米和 714 纳米处。计算得出了这些化合物相对于最具发射性物种的相对量子产率。

  DOI：

  10.1142/s1088424613501083

文献信息

• Porphyrin derivative-based tandem response nanochannels triggered by Zn²⁺ and NO
  作者：Xiao-Cui Liang、Shi-Qi Cheng、Qiang He、Zhong-Qiang Zhou、Yanxi Zhao、Yue Sun

  DOI：10.1039/d2cc02163c

  日期：——

  We describe tandem response nanochannels tailored with a porphyrin derivative that showed Zn²⁺ and NO gating with good stability and reversibility.

  我们描述了一种定制了卟啉衍生物的串联响应纳米通道，该通道表现出良好的稳定性和可逆性，具有Zn²⁺和NO门控特性。
• 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%.
• Correlations between functional porphyrin positions and accumulation in cancer cells
  作者：Toshifumi Tojo、Koshi Nishida、Takeshi Kondo、Makoto Yuasa

  DOI：10.1016/j.bmcl.2020.127437

  日期：2020.10

  Porphyrin is accumulated in tumours due to its interaction with protein. Cancer therapy with porphyrin as a carrier molecule is attracting attention. Porphyrin displays two functional sites termed beta- and meso-positions. A correlation between the functional position on the porphyrin molecule and the ability to accumulate in cancer cells is observed in the present study. The accumulation of porphyrin derivatives was determined by measuring fluorescence intensity after incubation for 2 and 24 h. The accumulation of cancer cells depended on the position and length of functional groups. Estimated binding constants between porphyrin and bovine serum albumin suggest that the position of functional groups leads to changes in binding affinity and influences the accumulation of porphyrin derivatives in cancer cells.
• Novel 5-benzazolyl-10,15,20-triphenylporphyrins and β,meso-benzoxazolyl-bridged porphyrin dyads: Synthesis, characterization and photophysical properties
  作者：Satyasheel Sharma、Mahendra Nath

  DOI：10.1016/j.dyepig.2011.07.022

  日期：2012.3

  Novel 5-benzazolyl-10,15,20-triphenylporphyrins and beta,meso-benzoxazole-linked diporphyrins were synthesized through La(OTf)(3) catalyzed reaction of newly prepared 5-(3,4-diam nophenyl)-10,15,20-triphenylporphyrin or 5-(3-amino-4-hydroxyphenyl)-10,15,20-triphenylporphyrin with aromatic aldehydes in 1,2-dichlorobenzene. On metalation with zinc acetate, freebase beta,meso-benzoxazole-linked diporphyrin was successfully converted to the Zn-Zn diporphyrin complex in good yield. The synthesized porphyrin analogues were characterized using electronic absorption, IR and H-1 NMR spectroscopy in addition to mass and elemental analyses. The fluorescence studies of 5-benzazolyl-10,15,20-triphenylporphyrins showed efficient intramolecular energy transfer from the pyrene and fluorene subunits to the porphyrin core. In addition, the fluorescence quenching observed in beta-meso-benzoxazolyl-bridged porphyrin dyads was attributed to the possible nonplanarity of it component of the diporphyrins. The freebase-Ni diporphyrin complex underwent strong emission quenching in comparison to that of freebase diporphyrin and dizinc diporphyrin analogues. (C) 2011 Elsevier Ltd. All rights reserved.
• LINDSEY, JONATHAN S.;BROWN, PHILIP A.;SIESEL, DAVID A., TETRAHEDRON, 45,(1989) N5, C. 4845-4866
  作者：LINDSEY, JONATHAN S.、BROWN, PHILIP A.、SIESEL, DAVID A.

  DOI：——

  日期：——