5,10,15,20-tetra(o-acetamidophenyl)porphyrin | 68949-51-9

• 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: 5,10,15,20-tetra(o-acetamidophenyl)porphyrin
• 英文别名: meso-tetrakis(o-acetamidophenyl)porphyrin；α,β,α,β-5,10,15,20-tetra(o-acetamidophenyl)porphyrin；meso-α,α,α,α-tetra-(o-acetamidophenyl)porphyrin；meso-β-(o-acetamidophenyl)-α,α,α-tris(o-acetamidophenyl)porphyrin；meso-tetra-α,α,α,α-(o-acetamidophenyl)porphyrin
• CAS: 68949-51-9；85166-02-5；88034-54-2；88034-55-3；88034-56-4
• 化学式: C₅₂H₄₂N₈O₄
• 分子量: 842.957
• InChiKey: MZLPUUOXBAMPSX-RCOMQYLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.16
• 重原子数：
  64.0
• 可旋转键数：
  8.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  173.76
• 氢给体数：
  6.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5,10,15,20-tetra(o-acetamidophenyl)porphyrin 在 三氟乙酸 作用下， 以 硝基苯 为溶剂， 生成 5,10,15,20-tetra(o-acetamidophenyl)porphyrin dication
  参考文献：
  名称：

  Bogat-skii, A. V.; Zakharov, K. S.; Zhilina, Z. I., Russian Journal of Organic Chemistry, 1983, vol. 19, # 8, p. 1513 - 1515

  摘要：

  DOI：
• 作为产物：
  描述：

  N-{2-[10,15,20-Tris-(2-acetylamino-phenyl)-porphyrinogen-5-yl]-phenyl}-acetamide 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 生成 5,10,15,20-tetra(o-acetamidophenyl)porphyrin
  参考文献：
  名称：

  Porphyrin Synthesis in Surfactant Solution:  Multicomponent Assembly in Micelles

  摘要：

  A synthesis of meso-substituted porphyrins in anionic sodium dodecyl sulfate micelles has been developed. Polar, functionalized aromatic aldehydes condense reversibly with pyrrole in the micellar phase. Oxidation of the porphyrinogen then provides functionalized porphyrins in yields of 10-48%. Hydrophobic aldehydes condense irreversibly to give low yields at practical substrate concentrations. Synthesis in D2O solution results in per-beta-deuterated porphyrins. A two-phase model is used to rationalize the dependence of porphyrin yield on reactant and surfactant concentration. Micelles are viewed as potential wells which promote porphyrinogen assembly by binding products more tightly than reactants.

  DOI：

  10.1021/jo9600161

文献信息

• Structural characterisation of the first mononuclear bismuth porphyrin
  作者：Bernard Boitrel、Zakaria Halime、Lydie Michaudet、Mohamed Lachkar、Lo�c Toupet

  DOI：10.1039/b309615g

  日期：——

  A single carboxylate picket bismuth porphyrin has been characterised in the solid state as the first instance of a non-dimeric structure; the carboxylate picket, bent over the macrocycle, is coordinated to the bismuth, inducing a significant distortion of the porphyrin core.

  一种单羧酸根铋卟啉在固态下首次被表征为非二聚体结构；羧酸根弯曲在大循环上，与铋配位，导致卟啉核心发生显著变形。
• Effect of an Oxygen-Binding Reaction at the Cobalt Porphyrin Site Fixed in a Polymer Membrane on Facilitated Oxygen Transport
  作者：Takayuki Suzuki、Yuji Soejima、Hiroyuki Nishide、Eishun Tsuchida

  DOI：10.1246/bcsj.68.1036

  日期：1995.3

  Oxygen transport was facilitated in polymer membranes bonded with new derivatives of [meso-α,α,α,α-tetrakis(o-pivalamidophenyl)porphyrinato]cobalt (CoPs). The oxygen-binding reactivity of fixed CoPs strongly influenced the facilitated oxygen transport. CoP having a larger cavity structure showed a more rapid reactivity and achieved a higher oxygen permeability in the membrane. There existed correlations

  与[内消旋-α,α,α,α-四(邻新戊酰氨基苯基)卟啉]钴(CoPs)的新衍生物结合的聚合物膜促进了氧的传输。固定 CoP 的氧结合反应性强烈影响促进的氧运输。具有较大腔结构的 CoP 显示出更快速的反应性并在膜中实现更高的透氧性。氧结合和解离速率常数与氧通过固定在膜中的 CoP 的扩散常数之间存在相关性。
• Coordination Tuning of Metal Porphyrins for Improved Oxygen Evolution Reaction
  作者：Haoyuan Lv、Xue‐Peng Zhang、Kai Guo、Jinxiu Han、Hongbo Guo、Haitao Lei、Xialiang Li、Wei Zhang、Ulf‐Peter Apfel、Rui Cao

  DOI：10.1002/anie.202305938

  日期：2023.9.18

  The nucleophilic attack of water or hydroxide on metal‐oxo units forms an O−O bond in the oxygen evolution reaction (OER). Coordination tuning to improve this attack is intriguing but has been rarely realized. We herein report on improved OER catalysis by metal porphyrin 1‐M (M=Co, Fe) with a coordinatively unsaturated metal ion. We designed and synthesized 1‐M by sterically blocking one porphyrin side with a tethered tetraazacyclododecane unit. With this protection, the metal‐oxo species generated in OER can maintain an unoccupied trans axial site. Importantly, 1‐M displays a higher OER activity in alkaline solutions than analogues lacking such an axial protection by decreasing up to 150‐mV overpotential to achieve 10 mA/cm² current density. Theoretical studies suggest that with an unoccupied trans axial site, the metal‐oxo unit becomes more positively charged and thus is more favoured for the hydroxide nucleophilic attack as compared to metal‐oxo units bearing trans axial ligands.

  摘要在氧进化反应（OER）中，水或氢氧化物对金属氧单元的亲核攻击会形成 O-O 键。通过配位调整来改善这种攻击令人感兴趣，但却很少实现。我们在此报告了金属卟啉 1-M（M=Co、Fe）与配位不饱和金属离子对 OER 催化作用的改进。我们设计并合成了 1-M，方法是用一个系链的四氮杂环十二烷单元对卟啉的一侧进行立体封堵。有了这种保护，在 OER 中生成的金属氧物种可以保持一个未被占用的反式轴向位点。重要的是，与缺乏这种轴向保护的类似物相比，1-M 在碱性溶液中显示出更高的 OER 活性，过电位可降低到 150 毫伏，电流密度可达 10 毫安/平方厘米。理论研究表明，与带有反式轴向配体的金属氧代单元相比，带有未被占用的反式轴向位点的金属氧代单元更带正电荷，因此更有利于受到氢氧化物的亲核攻击。
• Bogat-skii, A. V.; Zhilina, Z. I.; Krasnoshchekaya, S. P., Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 2035 - 2039
  作者：Bogat-skii, A. V.、Zhilina, Z. I.、Krasnoshchekaya, S. P.、Zakharova, R. M.

  DOI：——

  日期：——
• Bogatskii, A. V.; Zhilina, Z. I.; Danilina, N. I., Doklady Chemistry, 1980, vol. 251, p. 127 - 129
  作者：Bogatskii, A. V.、Zhilina, Z. I.、Danilina, N. I.

  DOI：——

  日期：——