2,3,7,8,12,13,17,18-octamethyl-5-phenylporphine | 109881-40-5

• 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
• 英文名称: 2,3,7,8,12,13,17,18-octamethyl-5-phenylporphine
• 英文别名: 2,3,7,8,12,13,17,18-octamethyl-5-phenyporphyrin
• CAS: 109881-40-5
• 化学式: C₃₄H₃₄N₄
• 分子量: 498.671
• InChiKey: AISMMOQLJAWMQK-DLIAXIFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.12
• 重原子数：
  38.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  57.36
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,3,7,8,12,13,17,18-octamethyl-5-phenylporphine 在 manganese(II) chloride tetrahydrate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2,3,7,8,12,13,17,18-octamethyl-5-phenylporphinato)chloromanganese(III)
  参考文献：
  名称：

  Role of the central manganese(III) ion in the hydrogen peroxide oxidation mechanism of (2,3,7,8,12,13,17,18-octaalkyl-5(5,10)(5,15)-phenyl(diphenyl)porphinato)chloromanganese(III)

  摘要：

  Complete kinetic description and spectral manifestation of the hydrogen peroxide oxidation of (2,3,7,8,12,13,17,18-octamethyl- and (2,3,7,8,12,13,17,18-octaethyl-5-phenylporphinato)chloromanganese(III), (2,3,7,8,12,13,17,18-octaethyl-5,10-diphenyl- and (2,3,7,8,12,13,17,18-octaethyl-5,15-diphenylporphinato)chloromanganese(III) complexes in water-organic solutions are presented. Two H2O2 concentration ranges with different reaction mechanisms and products were distinguished. The ion-molecular oxidation mechanism was substantiated and the key role of coordination of various hydrogen peroxide species, their activation, oxidation and reduction was demonstrated. Multiple substitution in the coordinated macrocycle was found to change the electronic state of the coordination site and quantitative characteristics of the oxidation; this can be used to develop the synthetic models of natural oxide reductases.

  DOI：

  10.1134/s0036023611120424
• 作为产物：
  描述：

  3,4,3',4'-tetramethyl-5,5'-methanediyl-bis-pyrrole-2-carboxylic acid diethyl ester 在 氢溴酸 、 对苯醌 、 potassium hydroxide 作用下， 以 水 、 乙二醇 、 正丁醇 为溶剂， 反应 6.25h， 生成 2,3,7,8,12,13,17,18-octamethyl-5-phenylporphine
  参考文献：
  名称：

  硝基取代的5-苯基-β-八烷基卟啉的酸碱性质的合成及分光光度法研究

  摘要：

  10,15-二硝基-5-苯基-2,3,7,8,12,13,17,18-八甲基卟啉，10,15,20-三硝基-5-苯基-2,3,7,8,12，合成并通过电子吸收鉴定了13,17,18-八甲基卟啉和10,15,20-三硝基-5-（4-硝基苯基）-2,3,7,8,12,13,17,18-八甲基卟啉，红外和1 NMR光谱学。通过在HClO 4中的分光光度滴定法研究了合成化合物的酸碱性质乙腈和1,8-二氮杂双环[5.4.0]十一碳-7-烯-乙腈体系在298 K下的分布。单质子化和双质子化以及单质子化和双质子化的电子吸收光谱参数和存在浓度范围确定相应配体的形式以及后者的酸和碱解离常数。进行了硝基对合成化合物反应性影响的比较分析。

  DOI：

  10.1134/s1070363217080187

文献信息

• Syntheses, properties and cellular studies of metallo-isoporphyrins
  作者：Sandra C. Mwakwari、Haijun Wang、Timothy J. Jensen、M. Graça H. Vicente、Kevin M. Smith

  DOI：10.1142/s108842461100380x

  日期：2011.9

  b-Bilene hydrochlorides are shown to be improved intermediates for the synthesis of metallo-isoporphyrins in enhanced yields (28% vs. 6%). Several new diamagnetic zinc(II) and a novel paramagnetic copper(II) isoporphyrin salts were also obtained using this approach. Metal-free isoporphyrins were also isolated. In vitro studies using human carcinoma HEp2 cells show that all metallo-isoporphyrins accumulate within cells and localize partially in the mitochondria. The zinc-isoporphyrins were found to be moderately phototoxic while the copper complex showed the lowest phototoxicity, maybe as a result of its paramagnetic nature.

  研究表明，b-苯盐酸盐是合成金属异卟啉的改良中间体，而且产率更高（28% 对 6%）。利用这种方法还获得了几种新的二磁性锌（II）和一种新的顺磁性铜（II）异卟啉盐。此外，还分离出了不含金属的异卟啉。利用人体癌细胞 HEp2 进行的体外研究表明，所有金属异卟啉都会在细胞内聚集，并部分定位于线粒体。研究发现，锌-异卟啉具有适度的光毒性，而铜复合物的光毒性最低，这可能是其顺磁性的结果。
• A Twisted and Partially Overlapping Porphyrin Dimer as a New Model of Special Pair in Photosynthetic Reaction Center
  作者：Atsuhiro Osuka、Kazuhiro Maruyama

  DOI：10.1246/cl.1987.825

  日期：1987.5.5

  twisted and partially overlapping porphyrin dimer bridged by a 1,1′-spirobiindane spacer was synthesized. Its biszinc complex and bismagnesium complex showed a split Soret band, indicating the exciton interaction of the two porphyrin ring. Bismagnesium complex underwent reversible one-electron oxidation 40 mV more easily than the corresponding monomeric porphyrin.

  合成了由 1,1'-螺二茚烷间隔物桥接的扭曲和部分重叠的卟啉二聚体。它的双锌配合物和铋镁配合物显示出分裂的索雷带，表明两个卟啉环的激子相互作用。双镁配合物比相应的单体卟啉更容易进行 40 mV 的可逆单电子氧化。
• Influence of the Structure of the Organic Moiety of Copper(II) Porphyrins on Their Reactivity toward Acids
  作者：O. V. Kosareva、M. E. Klyueva、T. N. Lomova、E. E. Suslova

  DOI：10.1007/s11176-005-0250-x

  日期：2005.3

  acid-induced dissociation of copper(II) porphyrin complexes with a high degree of meso - and β-substitution in the ligand was studied. The copper(II) complexes with octaethylporphyrins containing 0, 1, 2, 3, and 4 meso -phenyl substituents were ranked with respect to the stability. Octaβ-alkyl and unsymmetrical meso -phenyl substitution affects not only the quantitative characteristics of dissociation of the

  研究了酸诱导的铜（II）卟啉配合物在配体中具有高 介观 和β取代度的解离 。将具有0、1、2、3和4个 内消旋 苯基取代基的八乙基卟啉的铜（II）配合物进行 稳定性排序。Octaβ烷基和不对称 的内消旋 -苯基取代不仅影响复合物解离的定量特性，而且该过程的动力学关系。
• Phenyl-substituted porphyrins. 1. Synthesis of meso-phenyl-substituted porphyrins
  作者：S. A. Syrbu、T. V. Lyubimova、A. S. Semeikin

  DOI：10.1007/s10593-005-0050-6

  日期：2004.10
• Klyueva; Lomova; Berezin, Russian Journal of Inorganic Chemistry, 2003, vol. 48, # 8, p. 1238 - 1243
  作者：Klyueva、Lomova、Berezin、Semeikin

  DOI：——

  日期：——