5,5'-(phenylmethylene)bis(3-ethyl-2,4-dimethyl-1H-pyrrole) | 872332-81-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5,5'-(phenylmethylene)bis(3-ethyl-2,4-dimethyl-1H-pyrrole)
• 英文别名: 4-ethyl-2-[(4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)-phenylmethyl]-3,5-dimethyl-1H-pyrrole
• CAS: 872332-81-5
• 化学式: C₂₃H₃₀N₂
• 分子量: 334.505
• InChiKey: WXJMJWUBZZTIEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  31.6
• 氢给体数：
  2
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  5,5'-(phenylmethylene)bis(3-ethyl-2,4-dimethyl-1H-pyrrole) 在 三氟化硼乙醚 、 potassium tert-butylate 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 4.67h， 生成 4,4-dihydroxy-1,3,5,7-tetramethyl-2,6-diethyl-8-phenyl-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Use of F-BODIPYs as a Protection Strategy for Dipyrrins: Optimization of BF₂ Removal

  摘要：

  We recently reported the first general method for the deprotection of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacenes (F-BODIPYs) involving a microwave-assisted procedure for the removal of the BF2 moiety, and liberation of the corresponding free-base dipyrrin. Further optimization of the reaction has resulted in a more convenient and accessible protocol. The availability of this new methodology enables BF2-complexation to be used as a dipyrrin protection strategy. Herein lies a detailed examination of the deprotection reaction, with a view to optimization and gaining mechanistic insight, and its application in facilitating a multistep synthesis of pyrrolyldipyrrins.

  DOI：

  10.1021/jo3002003
• 作为产物：
  描述：

  4,4'-diethyl-3,3',5,5'-tetramethyl-6-phenylpyrromethene 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 以20%的产率得到5,5'-(phenylmethylene)bis(3-ethyl-2,4-dimethyl-1H-pyrrole)
  参考文献：
  名称：

  Microwave-assisted reduction of F-BODIPYs and dipyrrins to generate dipyrromethanes

  摘要：

  BODIPYs和dipyrrins被还原为dipyrromethanes，通过涉及乙二醇和甲氧基钠的反应。当苄醇代替乙二醇时，在微波辐射后向反应混合物中加入2,4-二硝基苯肼会导致产生1-苄基亚甲基-2-(2,4-二硝基苯基)肼，表明与dipyrromethane同时产生醛。

  DOI：

  10.1139/cjc-2013-0341

文献信息

• Design and Development of a New Pyrromethene Dye with Improved Photostability and Lasing Efficiency:  Theoretical Rationalization of Photophysical and Photochemical Properties
  作者：Soumyaditya Mula、Alok K. Ray、Manas Banerjee、Tandrima Chaudhuri、Kamalesh Dasgupta、Subrata Chattopadhyay

  DOI：10.1021/jo702346s

  日期：2008.3.1

  In an attempt to develop a photostable and efficient pyrromethene compound for use in liquid dye lasers, three congeners of the commercially available pyrromethene 567 (PM567) laser dye were synthesized and their photophysical properties, lasing efficiencies, and photochemical stabilities were studied. In general the presence of an aryl group at C-8 of the pyrromethene chromophore increased the photostability

  为了开发一种用于液体染料激光器的光稳定有效的吡咯亚甲基化合物，合成了三种同类的市售吡咯烯567（PM567）激光染料，并对其光物理性质，激光发射效率和光化学稳定性进行了研究。通常，吡咯亚甲基生色团的C-8处芳基的存在增加了光稳定性。具有C-8三甲氧基苯基部分的同类物之一显示出比PM567显着改善的激射参数。与PM567相比，新染料的光化学稳定性是其2倍，而在显着较低的浓度下，其激光发射效率与PM567相当。1 O 2）和与1 O 2反应的可能性。我们的计算与实验结果相符，并表明系统设计新的吡咯亚甲基生色团衍生物可能会导致改进的激光染料分子。
• Highly Sensitive Fluorescence Probes for Nitric Oxide Based on Boron Dipyrromethene ChromophoreRational Design of Potentially Useful Bioimaging Fluorescence Probe
  作者：Yu Gabe、Yasuteru Urano、Kazuya Kikuchi、Hirotatsu Kojima、Tetsuo Nagano

  DOI：10.1021/ja037944j

  日期：2004.3.1

  4-diaminophenyl)-2,6-bis(2-carboxyethyl)-4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene (DAMBO-P(H)), based on the BODIPY chromophore, as a highly sensitive fluorescence probe for nitric oxide (NO). DAMBO-P(H) had a low phi value of 0.002, whereas its triazole derivative (DAMBO-P(H)-T), the product of the reaction of DAMBO-P(H) with NO, fluoresced strongly (phi = 0.74). The change of

  已知硼二吡咯甲烯 (BODIPY) 在水溶液中具有高荧光量子产率 (phi)，但与荧光素相比，在生物应用中的利用并不多。我们开发了 8-(3,4-diaminophenyl)-2,6-bis(2-carboxyethyl)-4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s -indacene (DAMBO-P(H))，基于 BODIPY 发色团，作为一氧化氮 (NO) 的高灵敏度荧光探针。DAMBO-P(H) 具有 0.002 的低 phi 值，而其三唑衍生物 (DAMBO-P(H)-T)，即 DAMBO-P(H) 与 NO 反应的产物，发出强烈荧光（phi = 0.74 ）。发现荧光强度的变化受分子内光致电子转移（PeT）机制控制。DAMBO-P(H)的开发策略如下：（1）为了设计高灵敏度的NO探针，
• Fluorescent Properties of 8-Substituted BODIPY Dyes: Influence of Solvent Effects
  作者：Yuriy S. Marfin、Dmitry A. Merkushev、Sergey D. Usoltsev、Maria V. Shipalova、Evgeniy V. Rumyantsev

  DOI：10.1007/s10895-015-1643-9

  日期：2015.9

  Three boron-dipyrrine (BODIPY) based dyes with bulky substituents in 8-position of dipyrrin ligand have been synthesized and characterized. Photophysical properties of the obtained compounds have been investigated in different individual solvents and solvent mixtures. Investigated compounds was found to be intensive fluorescent molecular rotors. The influence of different solvent parameters and the substituent nature on rotor characteristics have been observed and discussed. Minor changes in the nature of 8-substituent does not influence the spectral properties, but the presence of nitrogen donor atom in the phenyl substituent could be used for the sensing of the donor-acceptor interactions with solvent or dissolved compounds. The new approach of spectral properties correlation with solvent parameters was proposed, the viscosity parameter should be taken into account in case of BODIPYs with bulky substituents. The intensity of fluorescence molecular rotor properties decrease gradually with the viscosity increase above 1 cP.

  我们合成并鉴定了三种基于硼-二吡啶（BODIPY）的染料，这些染料在二吡啶配体的 8 位上具有大取代基。在不同的溶剂和混合溶剂中，对所获化合物的光物理特性进行了研究。研究发现，所研究的化合物是密集荧光分子转子。研究人员观察并讨论了不同溶剂参数和取代基性质对转子特性的影响。8 取代基性质的微小变化不会影响光谱特性，但苯基取代基中氮供体原子的存在可用于感应供体-受体与溶剂或溶解化合物之间的相互作用。提出了光谱特性与溶剂参数相关性的新方法，对于具有大块取代基的 BODIPYs，应考虑粘度参数。荧光分子转子特性的强度随着粘度的增加而逐渐降低，超过 1 cP。
• An Improved Method for the Synthesis of <i>F</i>-BODIPYs from Dipyrrins and Bis(dipyrrin)s
  作者：Travis Lundrigan、Alexander E. G. Baker、Lauren E. Longobardi、Tabitha E. Wood、Deborah A. Smithen、Sarah M. Crawford、T. Stanley Cameron、Alison Thompson

  DOI：10.1021/ol300681w

  日期：2012.4.20

  An improved methodology for the synthesis of F-BODIPYs from dipyrrins and bis(dipyrrin)s is reported. This strategy employs lithium salts of dipyrrins as intermediates that are then treated with only 1 equiv of boron trifluoride diethyletherate to obtain the corresponding F-BODIPYs. This scalable route to F-BODIPYs renders high yields with a facile purification process involving merely filtration of

  报道了一种从二吡啶和双（双吡啶）合成F- BODIPY的改进方法。该策略采用双吡啶的锂盐作为中间体，然后仅用1当量的三氟化硼二乙基醚化物处理以获得相应的F- BODIPY。在许多情况下，这种简便的纯化方法仅涉及反应混合物通过硅藻土的过滤，因此这种可扩展的F -BODIPYs途径可实现高收率。
• The reaction of nitrones with pyrroles and furan: an easy access to heteroaromatic hydroxylamines and bis(heteroaryl)alkanes
  作者：Christophe Berini、Frédéric Minassian、Nadia Pelloux-Léon、Yannick Vallée

  DOI：10.1016/j.tetlet.2005.10.061

  日期：2005.12

  N-Benzylnitrones react with heteroaromatic compounds such as pyrroles or furan in the presence of hydrogen chloride. Either heteroaromatic N-benzylhydroxylamines, symmetrical or unsymmetrical 2,2'-bis(heteroaryl)alkanes could be selectively produced depending on the experimental conditions. (c) 2005 Elsevier Ltd. All rights reserved.