5,10,15-20四(4-甲氧基苯基)卟啉原 | 248606-49-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 5,10,15-20四(4-甲氧基苯基)卟啉原
• 英文名称: 5,10,15-20-tetrakis(4-methoxyphenyl)porphyrinogen
• CAS: 248606-49-7
• 化学式: C₄₈H₄₄N₄O₄
• 分子量: 740.902
• InChiKey: QTLDZRMYWYQEDI-UHFFFAOYSA-N

物化性质

• 密度：
  1.238±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.07
• 重原子数：
  56.0
• 可旋转键数：
  8.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  100.08
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5,10,15-20四(4-甲氧基苯基)卟啉原 在 溶剂黄146 、 硝基苯 作用下， 生成 5,10,15,20-tetrakis(4-methoxyphenyl)-21,22-dihydroporphyrin
  参考文献：
  名称：

  研究了在酸催化条件下硝基苯作为一种温和的脱氢剂的作用机理。

  摘要：

  质子化的硝基苯可用于使一系列已经具有至少一个双键的烃脱氢。动力学和光谱学结果以及已知的电极电势产生近似的极限，在该极限内可以预期质子化的硝基苯实现氢芳族化合物的脱氢。描述了苯并[j]荧蒽的高产率合成。

  DOI：

  10.1039/b210887a
• 作为产物：
  描述：

  5,10,15,20-tetrakis(4-methoxyphenyl)-21,22-dihydroporphyrin 在 溶剂黄146 、 三氟乙酸 、 锌 作用下， 反应 1.0h， 生成 5,10,15-20四(4-甲氧基苯基)卟啉原
  参考文献：
  名称：

  研究了在酸催化条件下硝基苯作为一种温和的脱氢剂的作用机理。

  摘要：

  质子化的硝基苯可用于使一系列已经具有至少一个双键的烃脱氢。动力学和光谱学结果以及已知的电极电势产生近似的极限，在该极限内可以预期质子化的硝基苯实现氢芳族化合物的脱氢。描述了苯并[j]荧蒽的高产率合成。

  DOI：

  10.1039/b210887a

文献信息

• Cellulose sulfuric acid as a biodegradable and recoverable solid acid catalyst for one pot synthesis of substituted pyrroles under solvent-free conditions at room temperature
  作者：Ali Rahmatpour

  DOI：10.1016/j.reactfunctpolym.2010.11.001

  日期：2011.1

  A new and efficient method for the preparation of N-substituted pyrroles from one-pot condensation reaction of 2,5-hexandione with amines and diamines in the presence of cellulose sulfuric acid (CSA) as a bio-supported catalyst at room temperature under solvent-free conditions is presented. This new protocol has the advantages of easy availability, stability, reusability and eco-friendly of the catalyst

  一种新型高效的方法，在室温下，在溶剂硫酸纤维素（CSA）存在下，由2,5-己二酮与胺和二胺一锅缩合反应制备N-取代的吡咯无条件。该新方案的优点是催化剂容易获得，稳定，可重复使用且对环境友好，产率高至优异，实验和后处理程序简单。
• Effects of methoxy-substituted metalloporphyrins in catalytic alkene epoxidation by n-<font>Bu</font>₄<font>NHSO</font>₅
  作者：Amineh Aghabali、Nasser Safari

  DOI：10.1142/s1088424610002136

  日期：2010.4

  TPPMnOAc and four different kinds of manganese tetraphenylporphyrin acetates were synthesized using different numbers of methoxy substituents in various positions of the phenyl rings. These porphyrins were used as catalysts in the epoxidation of various alkenes with tetra-n-butylammonium hydrogen monopersulfate (n- Bu ₄ NHSO ₅) as the oxidant and imidazole as the axial base. The following order of catalytic activity was obtained: TPPMnOAc ≥ T (2,3- OMeP ) PMnOAc > T (4- OMeP ) PMnOAc > T (3,4- OMeP ) PMnOAc > T (2,4,6- OMeP ) PMnOAc . By studying the UV-vis spectra in the reaction solution, the stability of the applied methoxy porphyrins and the effect of this factor on obtained yields were investigated. Lower catalytic activity in some of the methoxy porphyrins emphasized steric effects and special hydrogen bonding among the reaction elements. However, the stability of T (2,3- OMeP ) PMnOAc under our reaction condition was considerable and high activity was observed. By adding small amounts of alcohol to the reaction solution, the effect of the solvent mixture was previewed and steps were taken to identify the active intermediate of the catalyst in these conditions.

  利用苯环不同位置上不同数量的甲氧基取代基合成了 TPPMnOAc 和四种不同的四苯基卟啉醋酸锰。这些卟啉被用作催化剂，以四正丁基硫酸氢铵（n- Bu 4 NHSO 5）为氧化剂，咪唑为轴向碱，对各种烯烃进行环氧化反应。催化活性顺序如下TPPMnOAc ≥ T (2,3- OMeP ) PMnOAc > T (4- OMeP ) PMnOAc > T (3,4- OMeP ) PMnOAc > T (2,4,6- OMeP ) PMnOAc 。通过研究反应溶液中的紫外-可见光谱，研究了所应用的甲氧基卟啉的稳定性以及该因素对所得产率的影响。一些甲氧基卟啉的催化活性较低，强调了立体效应和反应元素之间特殊的氢键。然而，在我们的反应条件下，T (2,3- OMeP ) PMnOAc 具有很高的稳定性和活性。通过在反应溶液中加入少量的酒精，预览了混合溶剂的影响，并采取步骤确定了催化剂在这些条件下的活性中间体。
• Phosphorus Pentachloride (PCl5) Mediated Synthesis of Tetraarylporphyrins
  作者：Hashem Sharghi、Alireza Hassani Nejad

  DOI：10.1002/hlca.200390041

  日期：2003.2

  A new synthesis of porphyrins from pyrrole and substituted benzaldehydes is described, with PCl5 as catalyst. Aromatic aldehydes condense irreversibly with pyrrole in the presence of this catalyst, and aerobic oxidation of porphyrinogen provides functionalized porphyrins in yields of 20–65%.

  描述了用PCl 5作为催化剂由吡咯和取代的苯甲醛合成卟啉的新方法。在这种催化剂的存在下，芳香醛与吡咯不可逆地冷凝，卟啉原的需氧氧化可提供功能化的卟啉，产率为20-65％。
• Porphyrin synthesis using mechanochemistry: Sustainability assessment
  作者：Carla Gomes、Mariana Peixoto、Marta Pineiro

  DOI：10.1142/s1088424619500755

  日期：2019.7

  Looking for sustainable synthetic methodologies, mechanochemistry as a new tool for one-step and two-step approaches for the synthesis of meso-substituted porphyrins was explored. The best results were obtained in a two-step procedure, under liquid-assisted grinding in the oxidation step using 2-methyltetrahydrofuran, an environmentally acceptable solvent, and MnO₂ as a heterogeneous oxidant. The sustainability was assessed using two sustainability metrics, E-factor and EcoScale, which allow comparison between procedures and methods.

  为了寻找可持续的合成方法，研究人员探索了机械化学作为一步法和两步法合成中取代卟啉的新工具。在两步法中，使用环境可接受的溶剂 2-甲基四氢呋喃和作为异相氧化剂的二氧化锰在氧化步骤中进行液体辅助研磨，获得了最佳结果。可持续发展性的评估采用了两个可持续发展指标，即 E 因子和 EcoScale，这两个指标允许对不同的程序和方法进行比较。
• Beneficial effects of salts on an acid-catalyzed condensation leading to porphyrin formation
  作者：Feirong Li、Kexin Yang、John S. Tyhonas、Kristy A. MacCrum、Jonathan S. Lindsey

  DOI：10.1016/s0040-4020(97)00770-9

  日期：1997.9

  and the rate of formation of the porphyrin. Yield increases in the presence of salt were observed with catalysis by BF3·O(Et)2, BF3·2H2O, and CF3CO2H. Significant salt effects also were observed with BF3·O(Et)2 or CF3CO2H in the solvent diethyl ether, but the maximum yield was 15%. A survey of nine aldehydes showed yield improvements of up to 2-fold in six cases in the presence of salt. During the pyrrole-aldehyde

  将多种盐之一添加到室温，两步，一个烧瓶中，在0.1 M下反应，形成四苯基卟啉（TPP），产率最高提高2倍。在21种不溶性盐中，有12种增加了收率，有6种没有效果，有3种减少了收率。这给了增加的盐涵盖不同的阳离子，但只限于阴离子氯- ，溴- ，我-或Ph 4乙-而SO 4 2-，F - ，或BF 4 -没有给出改善的产率。所有7克的可溶性四烷基铵或四苯基鏻盐（F - ，氯-中，Ph 4乙-，PF 6 - ，或HSO 4 -的抗衡离子）进行了调查，这给了> 1.5倍的产量增加。因此，在含有0.1当量的NaCl（5.85 mg / 10 mL CH 2 Cl 2）或0.0031当量的苄基三丁基铵的CH 2 Cl 2中，用10 -2 M BF 3 ·O（Et）2催化的10 -1 M吡咯-苯甲醛缩合反应氯化物（Bu 3BzlNCl）（基于[苯甲醛]）的收率约为50％，而无盐反应的收率约为25％。通过