5-(3,4,5-trimethoxyphenyl)dipyrromethane | 167482-90-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(3,4,5-trimethoxyphenyl)dipyrromethane
• 英文别名: 2,2 inverted exclamation mark-[(3,4,5-Trimethoxyphenyl)methylene]bis(1H-pyrrole)；2-[1H-pyrrol-2-yl-(3,4,5-trimethoxyphenyl)methyl]-1H-pyrrole
• CAS: 167482-90-8
• 化学式: C₁₈H₂₀N₂O₃
• 分子量: 312.368
• InChiKey: MHPULFZRDSGNKH-UHFFFAOYSA-N

物化性质

• 熔点：
  164 °C
• 沸点：
  498.4±45.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  59.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(3,4,5-trimethoxyphenyl)dipyrromethane 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 0.75h， 以69%的产率得到5-(3,4,5-trimethoxyphenyl)dipyrromethene
  参考文献：
  名称：

  原始卟啉前体及其衍生物的合成及其抗原生动物活性

  摘要：

  血红素在非洲锥虫Leishmania sp。中的重要性。和疟原虫属。代谢证明通过干扰血红素代谢来考虑卟啉及其前体和衍生物作为潜在抗寄生虫剂的潜力。因此，评估了二十四种卟啉前体和衍生物对利什曼原虫，布鲁氏锥虫和疟原虫。对抗布鲁氏锥虫的最佳活性化合物是一种新的卟啉衍生物。化合物4i的MEC值为6.25μM，证明在体内有进一步的应用评估。而这些化合物并不反对的无鞭毛体intramacrophage活性大号。 donovani，另一种新的卟啉衍生物，化合物4f在20 nM时具有体外抗恶性疟原虫活性，在伯氏疟原虫/ Swiss小鼠模型中观察到小鼠存活略有延迟，浓度为50μmol/ kg /天×4。依赖于对卟啉行为的更好了解而开发的寄主相对于宿主细胞而言。

  DOI：

  10.1016/j.ejmech.2013.06.002
• 作为产物：
  描述：

  吡咯 、 3,4,5-三甲氧基苯甲醛 在 三氟乙酸 作用下， 反应 1.5h， 以33%的产率得到5-(3,4,5-trimethoxyphenyl)dipyrromethane
  参考文献：
  名称：

  Responsive and mitochondria-specific ruthenium(ii) complex for dual in vitro applications: two-photon (near-infrared) induced imaging and regioselective cell killing

  摘要：

  一种线粒体可穿透的钌(II)复合物被设计为响应探针，可用于增强单线态氧的形成（ΦΔ = 0.93），并在紫外线和近红外激光激发下导致细胞内局部损伤。

  DOI：

  10.1039/c0cc01848a

文献信息

• Chromophores
  申请人：——

  公开号：US20030203888A1

  公开（公告）日：2003-10-30

  The present invention relates to novel porphyrin and porphyrin-based chromophores and sets of porphyrin and porphyrin-based chromophores, which may be particularly useful in a range of photodynamic applications, including photochemotherapy and fluorescence analysis and imaging. In particular, the present invention provides new and useful porphyrin, chlorin and bacteriochlorin chromophores; methods for the production of such chromophores; and methods for the use of such chromophores in analysis and in medicine.

  本发明涉及新型卟啉和基于卟啉的色素以及卟啉和基于卟啉的色素组合，这些色素在一系列光动力应用中可能特别有用，包括光化疗和荧光分析与成像。具体而言，本发明提供了新型有用的卟啉、叶绿素和细菌叶绿素色素；生产此类色素的方法；以及在分析和医学中使用此类色素的方法。
• Utility of dipyrromethane in the synthesis of some new A2B2 porphyrin and their related porphyrin like derivatives with their evaluation as antimicrobial and antioxidant agents
  作者：Ahmed A. Fadda、Eman El-Gendy、Hala M. Refat、Eman H. Tawfik

  DOI：10.1016/j.dyepig.2020.109008

  日期：2021.7

  afforded some new porphyrin like and A2B2 porphyrin derivatives 4a-g and 5a-d, respectively. Biological evaluation of the newly synthesized compounds 4a-g and 5a-d showed promising activity as antimicrobial and antioxidant agents. Compounds 4c,4e,4g,5c, and 5d exhibited the highest antimicrobial activity, whereas, compounds 4a,4f,5a,5b, and 5d recorded the highest antioxidant activity.

  在这项工作中，在室温和无溶剂条件下，由醛和过量的吡咯合成了二吡咯甲烷衍生物2a，b。二吡咯甲烷2a，b与不同的芳族醛在盐酸或对甲苯磺酸作为催化剂的存在下反应，分别得到一些新的卟啉类和A 2 B 2卟啉衍生物4a-g和5a-d。对新合成的化合物4a-g和5a-d的生物学评估显示，其具有抗微生物和抗氧化剂作用。化合物4c，4e，4g，5c和5d表现出最高的抗菌活性，而化合物4a，4f，5a，5b和5d表现出最高的抗氧化活性。
• Modulation of energy levels by donor groups: an effective approach for optimizing the efficiency of zinc-porphyrin based solar cells
  作者：Bo Liu、Weihong Zhu、Yueqiang Wang、Wenjun Wu、Xin Li、Baoqin Chen、Yi-Tao Long、Yongshu Xie

  DOI：10.1039/c2jm16804a

  日期：——

  In the design of efficient sensitizers for dye-sensitized solar cells (DSSCs), it is vital to modulate the HOMO and LUMO orbitals by introducing suitable donor and acceptor groups. In this respect, triphenylamine has been extensively used as the donor group. Porphyrin has strong absorption in the UV-Vis range, which makes it a promising dye candidate. In addition, a porphyrin molecule contains eight β positions and four meso-positions, which may be conveniently utilized for introducing multiple donor and acceptor moieties. In this work, various numbers of triphenylamine and trimethoxyphenyl groups are introduced to the porphyrin meso-positions as electron donors, with the aim to systematically modulate the energy levels and investigate the effect on the efficiency of the DSSCs. The HOMO–LUMO energy gaps remain almost constant irrespective of the donor groups, thus, the variation of the donors leads to a contradictory effect on the processes of electron injection and dye regeneration. In the case of the zinc porphyrin with two triphenylamine units and one trimethoxyphenyl group as the electron donors (M3T2P), moderate and well-matched HOMO and LUMO energy levels are observed, thus affording high efficiencies for both the electron injection and the dye regeneration processes. The overall conversion efficiencies (η) of the DSSCs based on these dyes lie in the range of 2.70–5.45%, with the optimized performance achieved by M3T2P, which can be rationalized by the efficient electron injection and dye regeneration processes, and the long electron lifetime, as demonstrated by the electrochemical impedance spectroscopy measurements. These results provide further insights into the strategy for elevating the efficiencies of DSSCs, especially those based on porphyrins, simply by modulating the electron donor groups.

  在设计用于染料敏化太阳能电池（DSSC）的高效敏化剂时，通过引入合适的供体和受体基团来调节 HOMO 和 LUMO 轨道至关重要。在这方面，三苯胺已被广泛用作供体基团。卟啉在紫外可见光范围内有很强的吸收能力，因此是一种很有前途的候选染料。此外，卟啉分子包含 8 个 β 位和 4 个中间位，可方便地用于引入多个供体和受体分子。在这项研究中，卟啉中位引入了不同数量的三苯胺基团和三甲氧基苯基基团作为电子供体，目的是系统地调节能级并研究其对 DSSC 效率的影响。无论供体基团如何，HOMO-LUMO 能隙几乎保持不变，因此，供体的变化会对电子注入和染料再生过程产生相互矛盾的影响。而以两个三苯胺单元和一个三甲氧基苯基为电子供体的卟啉锌（M3T2P），其 HOMO 和 LUMO 能级适中且匹配良好，因此电子注入和染料再生过程的效率都很高。基于这些染料的 DSSC 的总体转换效率（η）介于 2.70% 至 5.45% 之间，其中 M3T2P 实现了最佳性能，这可以通过高效的电子注入和染料再生过程以及较长的电子寿命得到合理解释，电化学阻抗谱测量结果也证明了这一点。这些结果使人们进一步了解了通过调节电子供体基团来提高 DSSC（尤其是基于卟啉的 DSSC）效率的策略。
• Unique versatility of Amberlyst 15. An acid and solvent-free paradigm towards synthesis of bis(heterocyclyl)methane derivatives
  作者：Kamaljit Singh、Shivali Sharma、Amit Sharma

  DOI：10.1016/j.molcata.2011.07.007

  日期：2011.8

  Bis(heterocyclyl)methanes, key intermediates for a variety of chemical, biochemical and material science relevant targets, have been obtained in a synthetically useful manner using Amberlyst 15 ion-exchange resin. This method promises versatility, cost-effectiveness, and efficiency. (C) 2011 Elsevier B.V. All rights reserved.
• 3,5-Diformylboron Dipyrromethenes as Fluorescent pH Sensors
  作者：Sheri Madhu、Malakalapalli Rajeswara Rao、Mushtaque S. Shaikh、Mangalampalli Ravikanth

  DOI：10.1021/ic102499h

  日期：2011.5.16

  A series of boron dipyrromethene (BODIPY) dyes containing two aldehyde functional groups at the 3 and 5 positions have been synthesized in low-to-decent yields in two steps. In the first step, the meso-aryl dipyrromethanes were treated with POCl(3) in N,N-dimethylformamide to afford 1,9-diformylated dipyrromethanes. In the second step, the diformylated dipyrromethanes were first in situ oxidized with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and then reacted with BF(3)center dot OEt(2) to afford 3,5-diformylboron dipyrromethenes. The X-ray structural analysis indicated that the aldehyde groups are involved in intramolecular hydrogen bonding with fluoride atoms, which may be responsible for the stability of the diformylated BODIPY compounds. The presence of two formyl groups significantly alters the electronic properties, which is clearly evident in downfield shifts in the (1)H and (19)F NMR spectra, bathochromic shifts in the absorption and fluorescence spectra, better quantum yields, and increased lifetimes compared to 3,5-unsubstituted BODIPYs. Furthermore, 3,5-diformylboron dipyrromethenes are highly electron-deficient and undergo facile reductions compared to unsubstituted BODIPYs. These compounds exhibit pH-dependent on/off fluorescence and thus act as fluorescent pH sensors.