5-(o-aminophenyl)-10,15,20-(tritolyl)porphyrin | 131352-79-9

• 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-(o-aminophenyl)-10,15,20-(tritolyl)porphyrin
• 英文别名: 5-(2-aminophenyl)-10,15,20-tris(4-methylphenyl)porphyrin
• CAS: 131352-79-9
• 化学式: C₄₇H₃₇N₅
• 分子量: 671.844
• InChiKey: IADCIJJVQVUPEE-ZQANTMHOSA-N

物化性质

• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.83
• 重原子数：
  52.0
• 可旋转键数：
  4.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  83.38
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-(o-aminophenyl)-10,15,20-(tritolyl)porphyrin 以 四氢呋喃 、 吡啶 为溶剂， 生成 copper 5-(2-((((2,2,5,5-tetramethyl-1-oxypyrrolin-3-yl)amino)carbonyl)amino)phenyl)-10,15,20-tritolylporphyrin
  参考文献：
  名称：

  Metal-nitroxyl interactions. 22. Copper-nitroxyl spin-spin interaction as a probe of weak orbital overlaps in derivatives of copper tetraphenylporphyrin

  摘要：

  DOI：

  10.1021/ic50224a042
• 作为产物：
  描述：

  5-(2-nitrophenyl)-10,15,20-tristolylporphyrin 在 盐酸 、 tin(ll) chloride 作用下， 反应 0.67h， 生成 5-(o-aminophenyl)-10,15,20-(tritolyl)porphyrin
  参考文献：
  名称：

  胡萝卜素-卟啉二元组中的三重态和单重态能量转移：连接键的作用。

  摘要：

  已经制备了一系列类胡萝卜素二元分子，其中类胡萝卜素在中间芳香环的邻位、间位或对位共价连接到四芳基卟啉，并使用稳态和瞬态荧光发射、瞬态荧光对这些分子进行了研究。吸收和 1 H NMR 方法。已经观察到从卟啉部分到类胡萝卜素的三线态能量转移，以及从类胡萝卜素多烯到卟啉的单线态能量转移

  DOI：

  10.1021/ja00036a002

文献信息

• Reversible two-electron-one-proton systems in the ring-centered oxidation of metalloporphyrins bearing secondary amide-linked superstructures
  作者：Asma El-Kasmi、Doris Lexa、Philippe Maillard、Michel Momenteau、Jean Michel Saveant

  DOI：10.1021/ja00005a022

  日期：1991.2

  Complexes of porphyrins derived from tetraphenylporphyrin by substitution of the ortho position of the phenyl rings by secondary amide groups in a basket-handle or picket configuration undergo a reversible two-electron oxidation whatever the nature of the central metallic ion, Cu2+, Zn2+, Ni2+, Fe3+, Co3+, in solvents such as 1,2-dichloroethane, methylene chloride, and benzonitrile. The reaction mechanism is investigated by cyclic voltammetry (as a function of the scan rate and the addition of a base or an acid) and UV-vis-near-IR and Fourier transform IR thin-layer spectroelectrochemistry. The reaction product is an endogeneous isoporphyrin resulting from the formation of an oxazine ring formed upon condensation of a meso carbon of the porphyrin dication with the oxygen of the amide group. The same reaction occurs with tertiary amide substituents, but in the case of secondary amide the concomitant loss of the amide proton facilitates the formation of the isoporphyrin. It thus drives the uphill disproportionation of two cation radicals to the right-hand side to such an extent that the uptake of the two electrons takes place at nearly the same potential. The reduction of the internal isoporphyrin is also a two-electron reaction at low scan rates with both the secondary and tertiary amide substituted compounds. The two-electron character of the isoporphyrin reduction is the result of an autocatalytic process in which the porphyrin cation radical serves as redox catalyst.
• Synthesis, Spectroscopy, and Photocytotoxicity of Glycosylated Amino Acid Porphyrin Derivatives as Promising Molecules for Cancer Phototherapy
  作者：V. Sol、J. C. Blais、V. Carré、R. Granet、M. Guilloton、M. Spiro、P. Krausz

  DOI：10.1021/jo982499+

  日期：1999.6.1

  To obtain molecules that can target malignant cells, two series of new meso glucosylporphyrins bearing amino acid residues are synthesized in four steps. The first series contained n meso glycosyl moieties and (4 - n) alanyl groups on the ortho or para positions of the meso phenyl. In the second series, the carbohydrate moiety is separated from the aryl substituent by a serine unit. Starting from p- or o-nitrobenzaldehyde, p- or o-acetylbenzaldehyde or -tolualdehyde, and pyrrole, the glycosylnitrophenylporphyrins 3-6 and tritolylporphyrins 8a,b are synthesized under optimized conditions tailored from Lindsey's method. The nitro function is then reduced and N-Fmoc-L-alanine or acetylglycosylated N-Fmoc-serine are coupled on the amino function. A detailed H-1 and C-13 NMR study allows complete structural elucidation. The UV-visible fluorescence and MALDI mass spectra are presented. Compounds 19-22 produced O-1(2), and photocytotoxicities against the K562 leukemia cell line are compared to hematoporphyrin. As a result of their sensitizing abilities, these resultant compounds are of considerable interest for photodynamic therapy.
• THE USE OF CAROTENOPORPHYRINS AS TUMOR LOCALIZING AGENTS FOR DIAGNOSIS, VISUALIZATION AND DELIVERY OF SENSITIZERS TO TUMOR TISSUES
  申请人：ARIZONA BOARD OF REGENTS

  公开号：EP0626866A1

  公开（公告）日：1994-12-07
• EP0626866A4
  申请人：——

  公开号：EP0626866A4

  公开（公告）日：1994-12-21
• US5286474A
  申请人：——

  公开号：US5286474A

  公开（公告）日：1994-02-15