5-(4-chlorophenyl)-10,15,20-triphenylporphyrin | 133513-02-7

• 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-chlorophenyl)-10,15,20-triphenylporphyrin
• CAS: 133513-02-7
• 化学式: C₄₄H₂₉ClN₄
• 分子量: 649.194
• InChiKey: WGOXZBQCFRYOPR-LWQDQPMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.98
• 重原子数：
  49.0
• 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

• 作为产物：
  描述：

  5-(p-aminophenyl)-10,15,20-triphenylporphine 在 盐酸 、 溶剂黄146 、 copper dichloride 、 亚硝酸异戊酯 作用下， 生成 5-(4-chlorophenyl)-10,15,20-triphenylporphyrin
  参考文献：
  名称：

  Synthesis of tetraphenylporphines with active groups in the phenyl rings 6. Synthesis of monosubstituted tetraphenylporphines by diazotization

  摘要：

  DOI：

  10.1007/bf00476980

文献信息

• Iodine-catalyzed one-pot synthesis of unsymmetrical meso-substituted porphyrins
  作者：Benjamin Boëns、Pierre-Antoine Faugeras、Julien Vergnaud、Romain Lucas、Karine Teste、Rachida Zerrouki

  DOI：10.1016/j.tet.2010.01.055

  日期：2010.3

  5-(4-nitrophenyl)-10,15,20-triphenylporphyrin is well established, but its synthesis requires two steps and is not very practical. This article describes an iodine-catalyzed one-pot synthesis of this unsymmetrical porphyrin that uses commercial reagents and reactants as such, without prior distillation. Unsymmetrical mono functionalized porphyrins with various functional groups have also been obtained to validate

  已经确定了5-（4-硝基苯基）-10,15,20-三苯基卟啉的广泛用途，但是其合成需要两个步骤并且不是很实用。本文介绍了这种不对称卟啉的碘催化一锅法合成方法，该方法不需事先蒸馏即可使用市售试剂和反应物。还获得了具有各种官能团的不对称单官能卟啉，以验证该方法。还研究了官能团（供体或受体）的电子效应的影响。
• Synthesis and characterization of six nonsymmetric A3B porphyrins with p-chlorophenyl as meso-substituent A or B and determination of their photodynamic activity
  作者：Erika L. Loredo-Calderón、Susana T. López-Cortina、Pilar Carranza-Rosales、Ezequiel Viveros-Valdez、Eugenio Hernández-Fernández、Mario Fernández-Zertuche

  DOI：10.1007/s00044-016-1600-4

  日期：2016.8

  generation of reactive oxygen species mediated by light-activated photosensitizing agents. One of the most promising types of photosensitizers is tetrapyrrolic macrocyclic compounds, such as meso-substituted porphyrins. In the present study, the synthesis of nonsymmetric porphyrins A3B was accomplished, with p-chlorophenyl as B or A meso-substituent along with hydroxyl group, methoxyl group, or hydrogen

  通过产生由光活化的光敏剂介导的活性氧，光动力疗法是治疗实体瘤的有前途的替代方法。光敏剂最有前景的类型之一是四吡咯大环化合物，例如内消旋取代的卟啉。在本研究中，完成了不对称卟啉A 3 B的合成，其中对氯苯基为B或A的内消旋基以及羟基，甲氧基或氢原子作为内消旋基中苯基的取代基设计位置和靶分子以评估这些不对称分布的疏水和亲水部分的协同作用。已证明对人乳腺癌和子宫颈癌细胞系（分别为MCF-7和HeLa细胞）具有细胞毒作用。进行了末端脱氧核苷酸转移酶dUTP缺口末端标记测定和形态学研究，以阐明最具活性的化合物的部分细胞损伤机制。
• Palladium-Catalyzed Cross-Coupling Reactions of Brominated Porphyrins with Functionalized Organomagnesium Reagents: Direct Preparation of Functional-Group-Bearing Free Base Porphyrins
  作者：Toshikatsu Takanami、Noriaki Sugita、Ikumi Tsuchiya

  DOI：10.3987/com-15-s(t)20

  日期：——

  The direct preparation of free-base porphyrins possessing reactive functional groups such as esters, halides, amide, nitriles, and acetals is described. This method relies on a simple one-pot procedure that involves sequential palladium-catalyzed cross-coupling of brominated free-base porphyrins with functionalized aryl and alkenylmagnesium reagents, which are readily prepared by iodine magnesium exchange of the corresponding organic iodides with the turbo Grignard reagent i-PrMgCl center dot LiCl, followed by demetallation of the resulting magnesium porphyrins under very mild conditions involving either a 1.2 M aqueous methanol solution of HCl or a 0.1 M methanol solution of citric acid at ambient temperature.
• Kudrevich, Svetlana V.; Ali, Hasrat; Lier, Johan E., Journal of the Chemical Society. Perkin transactions I, 1994, # 19, p. 2767 - 2774
  作者：Kudrevich, Svetlana V.、Ali, Hasrat、Lier, Johan E.

  DOI：——

  日期：——
• SYRBU, S. A.;SEMEJKIN, A. S.;BEREZIN, B. D., XIMIYA GETEROTSIKL. SOED.,(1990) N1, S. 1507-1509
  作者：SYRBU, S. A.、SEMEJKIN, A. S.、BEREZIN, B. D.

  DOI：——

  日期：——