2,3,7,8,12,13,17,18-octaphenylporphyrin | 2537-82-8

• 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-octaphenylporphyrin
• 英文别名: octaphenylporphyrin；β-octaphenylporphyrin；Octaphenylporphin；2,3,7,8,132,13,17,18-Oktamethyl-porphin；2,3,7,8,12,13,17,18-octaphenylporphin
• CAS: 2537-82-8
• 化学式: C₆₈H₄₆N₄
• 分子量: 919.14
• InChiKey: LSQRFOGUAZKHIW-AGZLKQOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.0
• 重原子数：
  72.0
• 可旋转键数：
  8.0
• 环数：
  13.0
• 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

• 作为反应物：
  描述：

  2,3,7,8,12,13,17,18-octaphenylporphyrin 在 copper diacetate 、 溶剂黄146 作用下， 生成 copper(II) 2,3,7,8,12,13,17,18-octaphenylporphyrinate
  参考文献：
  名称：

  Kinetics of the formation of copper β-octaphenylporphyrin complexes in pyridine and acetic acid

  摘要：

  The formation kinetics of copper beta-octaphenylporphyrin complexes in pyridine and acetic acid is reported and is compared with that of copper beta-octamethylporphyrin and dodecaphenylporphyrin complexes. The introduction of electron-donating or electron-withdrawing substituents in the beta-positions of the porphyrin macrocycle change the rate of the complexation reaction by at most one order of magnitude. On passing from the planar porphyrin macrocycle to the heavily distorted one, the rate of the reaction in pyridine (electron donor solvent) and acetic acid (electron acceptor solvent) increases and decreases, respectively, by several orders of magnitude.

  DOI：

  10.1134/s0036023610090275
• 作为产物：
  描述：

  octaphenylporphyrinogen 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醇 、 苯 为溶剂， 反应 0.5h， 生成 2,3,7,8,12,13,17,18-octaphenylporphyrin
  参考文献：
  名称：

  A new synthesis of octaarylporphyrin: Naturally occurring porphyrin mimics.

  摘要：

  通过 3，4-二芳基吡咯与甲醛的环化反应以及随后的 DDQ 氧化反应，高产率地获得了八芳基卟啉。该反应的中间产物被鉴定为卟啉原和卟吩二甲烯，并通过光谱学对其进行了表征。

  DOI：

  10.1248/cpb.38.264

文献信息

• Synthesis of Octaalkyl- and Octaarylporphyrins from Nitroalkenes
  作者：Noboru Ono、Kazuhiro Maruyama

  DOI：10.1246/cl.1988.1511

  日期：1988.9.5

  Symmetrically substituted octaalkyl- and octaarylporphyrins are readily prepared by the reduction of 2-ethoxycarbonyl-3,4-diarkyl (or diaryl)pyrroles with LiAlH4 followed by treatment with acetic acid and oxidizing agents.

  对称取代的八烷基和八芳基卟啉可以通过用LiAlH4还原2-乙氧基羧基-3,4-二烷基（或二芳基）吡咯，随后用醋酸和氧化剂处理来容易地制备。
• Synthesis of Sterically Overcrowded Deca- and Undecaphenylporphyrins via Mixed Condensation of 3,4-Diphenylpyrrole with Benzaldehyde and Formaldehyde
  作者：Jun Takeda、Mitsuo Sato

  DOI：10.1246/cl.1994.2233

  日期：1994.12

  Sterically overcrowded unsymmetrical porphyrins bearing ten and eleven phenyl groups are synthesized using mixed condensation of diphenylpyrrole with benzaldehyde and formaldehyde and characterized by FAB-MS, UV-VIS, and NMR spectra.

  利用二苯基吡咯与苯甲醛和甲醛的混合缩合，合成了带有十个和十一个苯基的立体过密非对称卟啉，并利用 FAB-MS、UV-VIS 和 NMR 光谱对其进行了表征。
• Ono, Noboru; Miyagawa, Hirokazu; Ueta, Takahiro, Journal of the Chemical Society. Perkin transactions I, 1998, # 10, p. 1595 - 1601
  作者：Ono, Noboru、Miyagawa, Hirokazu、Ueta, Takahiro、Ogawa, Takuji、Tani, Hiroyuki

  DOI：——

  日期：——
• Electronic and steric effects of substituents on the coordinating properties of porphyrins
  作者：S. G. Pukhovskaya、B. A. Efimovich、A. S. Semeikin、E. A. Kolodina、O. A. Golubchikov

  DOI：10.1134/s107036321203019x

  日期：2012.3

  Kinetics of the formation of zinc complexes of porphyrin with various substituents was studied in acetic acid and pyridine. The introduction of strong electron-withdrawing substituents (nitro groups) to the meso-positions of the porphyrin macrocycle was shown to change the reaction rate by an order of magnitude or less compared to the phenyl-substituted analogs. However, the introduction of a large number of bulky substituents leads to the deformation of the porphyrin ligand and thus affects much stronger the coordination properties of porphyrins, decreasing or increasing the rate of the complexation reaction by several orders of magnitude.
• Effect of structural and electronic properties of substituents on the metal porphyrin formation kinetics
  作者：S. G. Pukhovskaya、V. A. Efimovich、O. A. Golubchikov

  DOI：10.1134/s0036023613040141

  日期：2013.4

  5,10,15-trinitro-2,3,7,8,12,13,17,18-octaethylporphyrin was synthesized and the kinetics of its coordination to zinc acetate was studied in comparison with previously studied beta-octamethylporphyrin, beta-octaphenylporphyrin, 5,10,15-triphenyl-2,3,7,8,12,13,17,18-octamethylporphyrin, and 5,10,15,20-tetraphenyl-2,3,7,8,12,13,17,18-octamethylporphine. The effect of structural and electronic properties of substituents on the kinetics of formation of metal porphyrins is analyzed. It is shown that the properties of 5,10,15-trinitro-2,3,7,8,12,13,17,18-octaethylporphyrin are determined by both strong electron-withdrawing influence of three nitro groups and by the distortion of the planar structure of the tetrapyrrole macrocycle.