bis-(4-ethyl-3,5-dimethyl-pyrrol-2-yl)-ethanedione | 783366-69-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: bis-(4-ethyl-3,5-dimethyl-pyrrol-2-yl)-ethanedione
• 英文别名: Bis-(4-aethyl-3,5-dimethyl-pyrrol-2-yl)-aethandion；1,2-bis(4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)ethane-1,2-dione
• CAS: 783366-69-8
• 化学式: C₁₈H₂₄N₂O₂
• 分子量: 300.401
• InChiKey: CZMOTDNBYDMWEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  65.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  bis-(4-ethyl-3,5-dimethyl-pyrrol-2-yl)-ethanedione 在 对甲苯磺酸 、 三氟乙酸 吡啶 、 sodium hydroxide 、 溶剂黄146 作用下， 以 二氯甲烷 、 乙二醇 、 甲苯 为溶剂， 反应 31.25h， 生成 13,33,53,74-tetraethyl-14,34,54,73-tetramethyl-11H,31H,51H,71H-2,6(2,3)-diquinoxalina-1,3,5,7(2,5)-tetrapyrrolacyclooctaphane
  参考文献：
  名称：

  轻松制备双二吡咯基喹喔啉桥联的膨胀卟啉。前所未有的[20]四卟啉-（2.1.2.1）的合成和结构表征。

  摘要：

  [结构：见正文]描述了一种空前的V形（2.1.2.1）扩展的卟啉，其中结合了扩展的pi共轭体系。它的有效合成依赖于使用新的全烷基四吡咯基喹喔啉构件，该构件构成了多功能制备新的含喹喔啉的大环化合物的理想中间体。

  DOI：

  10.1021/ol0606381
• 作为产物：
  描述：

  草酰氯 、 alkaline earth salt of/the/ methylsulfuric acid 在 乙醚 作用下， 生成 bis-(4-ethyl-3,5-dimethyl-pyrrol-2-yl)-ethanedione
  参考文献：
  名称：

  Fischer; Baumgartner; Ploetz, Justus Liebigs Annalen der Chemie, 1932, vol. 493, p. 1

  摘要：

  DOI：

文献信息

• Dipyrrolylquinoxaline difluoroborates with intense red solid-state fluorescence
  作者：Changjiang Yu、Erhong Hao、Tingting Li、Jun Wang、Wanle Sheng、Yun Wei、Xiaolong Mu、Lijuan Jiao

  DOI：10.1039/c5dt02012c

  日期：——

  A set of organic fluorescent dyes of dipyrrolylquinoxalines (PQs 4–6) and their BF2 complexes (BPQs 1–3) were synthesized from commercial reagents, and were characterized by their X-ray structural analysis, and optical and electrochemical properties. BPQs 1–3 showed intense broad absorption in the visible region in the solution-state. In comparison with that of PQs 4–6, there is an over 110 nm red-shift

  一组的dipyrrolylquinoxalines（PQS有机荧光染料4-6）和它们的BF 2配合物（BPQs 1-3）购自商业试剂合成，并且进行了表征可以通过X射线结构分析，以及光学和电化学性质。BPQ 1–3在溶液状态的可见光区域显示出强烈的广泛吸收。与PQ 4–6相比，BPQ 1–3（最大583 nm）的吸收最大值有超过110 nm的红移。有趣的是，除PQ 4之外，染料1-6均显示红色固态荧光，并具有中等至高的荧光量子产率。呈亮黄色固态荧光。BPQ 2–3的X射线结构显示了通过一个BF 2螯合具有一个吡咯单元的喹喔啉的平面结构，以及未配位的吡咯几乎垂直于NBN核心平面的取向（二面角为70–73°）。扩展的π共轭与观察到的光谱红移很好地吻合。这些染料通过喹喔啉部分的N原子与相邻吡咯的NH单元之间的分子间氢键形成了有序的分子间堆积结构。在它们的晶体堆积结构中缺少π-π堆积可能解释了这些染料有趣的强烈的固态荧光。
• Highly photostable ketopyrrolyl-BODIPYs with red aggregation-induced emission characteristics for ultrafast wash-free mitochondria-targeted bioimaging
  作者：Hao Wu、Xing Guo、Changjiang Yu、Wai-Yeung Wong、Erhong Hao、Lijuan Jiao

  DOI：10.1016/j.dyepig.2020.108209

  日期：2020.5

  Subcellular organelle-specific probes, including mitochondria-targeted fluorescent probes, have attracted enormous research interests because they can monitor or visualize the morphology or biological activities of specific organelles and play an indispensable role in disease diagnosis. To follow the process, highly specific and photostable fluorescent probes are in demand. However, commercially available mitochondria probes normally suffer from poor photostability under laser irradiation and aggregation caused quenching (ACQ) in the aggregate state. In this work, two simple aggregation-induced emission(AIE)-active meso-2-ketopyrrolyl BODIPYs were developed via a convenient one-pot synthetic procedure from 2-methylpyrrole and corresponding pyrrolyldiketone in the presence of BF3 center dot OEt2. The two AIE luminogens (AIEgens) both show very weak fluorescence (maximum emission peaks at 545 and 559 nm, respectively) in DMSO and strong near-infrared solid-state emission. The fluorescence was dramatically intensified and redshifted to 635 and 643 rim, respectively, when water fraction was increased up to above 95% in the DMSO/water mixtures. Both AlEgens were found to specifically "light up" the cell mitochondria with high biocompatibility. Interestingly, the staining process can be shortened for less than a minute after the addition of the AlEgens and without the involvement of a washing procedure, indicating an ultrafast and easy-to-operate staining protocol. Furthermore, their fluorescent images in deep tissue penetration were captured with a satisfied signal-to-noise ratio at a depth of 20 and 30 mu m along the direction of the z-axis. Importantly, both AlEgens exhibit high photostability under harsh continuous laser irradiation, demonstrating their potential application as in visualizing and tracking specific mitochondria-associated dynamic changes.
• Synthesis of functionalized dipyrrolyldiketones, precursors of quinoxaline-containing macrocycles
  作者：Florence Szydlo、Bruno Andrioletti、Eric Rose、Carine Duhayon

  DOI：10.1016/j.tetlet.2004.07.139

  日期：2004.9

  In the general context of molecular recognition, the need to design new ligands able to selectively bind small analytes is currently being subjected to intensive research. In this respect, and considering that polypyrrole ligands can play crucial roles in this area, we developed the synthesis of a new class of per-alkyl dipyrrolyldiketone building blocks. Further functionalization including oxidation, and conversion to the corresponding aza-analogue dimer of indolizine is described. (C) 2004 Elsevier Ltd. All rights reserved.
• Fischer; Baumgartner; Ploetz, Justus Liebigs Annalen der Chemie, 1932, vol. 493, p. 1
  作者：Fischer、Baumgartner、Ploetz

  DOI：——

  日期：——
• Facile Preparation of Doubly Dipyrrolylquinoxaline-Bridged Expanded Porphyrins. Synthesis and Structural Characterization of an Unprecedented [20]Tetraphyrin-(2.1.2.1)
  作者：Florence Szydlo、Bruno Andrioletti、Eric Rose

  DOI：10.1021/ol0606381

  日期：2006.5.1

  [structure: see text] An unprecedented V-shape (2.1.2.1) expanded porphyrin incorporating an extended pi-conjugated system is described. Its efficient synthesis relied on the use of a new peralkyl tetrapyrrolylquinoxaline building block that constitutes the ideal intermediate for the versatile preparation of new quinoxaline-containing macrocycles.

  [结构：见正文]描述了一种空前的V形（2.1.2.1）扩展的卟啉，其中结合了扩展的pi共轭体系。它的有效合成依赖于使用新的全烷基四吡咯基喹喔啉构件，该构件构成了多功能制备新的含喹喔啉的大环化合物的理想中间体。