tetraethyl 5,5'-(furan-2,5-diyl)bis(2-bromo-1H-pyrrole-3,4-dicarboxylate) | 1578203-56-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: tetraethyl 5,5'-(furan-2,5-diyl)bis(2-bromo-1H-pyrrole-3,4-dicarboxylate)
• CAS: 1578203-56-1
• 化学式: C₂₄H₂₄Br₂N₂O₉
• 分子量: 644.271
• InChiKey: UHMGBKZKVVIDGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  37.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  149.92
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  tetraethyl 5,5'-(furan-2,5-diyl)bis(2-bromo-1H-pyrrole-3,4-dicarboxylate) 在 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  A Hybrid Macrocycle with a Pyridine Subunit Displays Aromatic Character upon Uranyl Cation Complexation

  摘要：

  Reported here is a new hybrid macrocycle, cyclo[1]furan[1]pyridine[4]pyrrole (1), that bears analogy to the previously reported mixed heterocycle system cyclo[2]pyridine[4]pyrrole (2) and cyclo[6]pyrrole 3, an all-pyrrole 22 pi-electron aromatic expanded porphyrin. The oxidized, dianionic form of 1, [1-4H](2-), has been characterized as its uranyl complex. In contrast to 2 and 3 and in spite of the presence of a 2,6-disubstituted pyridine subunit, the uranyl complex of [1-4H](2-) displays solid-state structural and solution-phase spectroscopic features consistent with contributions to the overall electronic structure that involve a conjugated, (4n + 2) pi-electron aromatic periphery.

  DOI：

  10.1021/ja412520g
• 作为产物：
  描述：

  3,4-吡咯二羧酸二乙酯 在 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 N,N-dimethyl-d₆-formamide 为溶剂， 反应 28.17h， 生成 tetraethyl 5,5'-(furan-2,5-diyl)bis(2-bromo-1H-pyrrole-3,4-dicarboxylate)
  参考文献：
  名称：

  A Hybrid Macrocycle with a Pyridine Subunit Displays Aromatic Character upon Uranyl Cation Complexation

  摘要：

  Reported here is a new hybrid macrocycle, cyclo[1]furan[1]pyridine[4]pyrrole (1), that bears analogy to the previously reported mixed heterocycle system cyclo[2]pyridine[4]pyrrole (2) and cyclo[6]pyrrole 3, an all-pyrrole 22 pi-electron aromatic expanded porphyrin. The oxidized, dianionic form of 1, [1-4H](2-), has been characterized as its uranyl complex. In contrast to 2 and 3 and in spite of the presence of a 2,6-disubstituted pyridine subunit, the uranyl complex of [1-4H](2-) displays solid-state structural and solution-phase spectroscopic features consistent with contributions to the overall electronic structure that involve a conjugated, (4n + 2) pi-electron aromatic periphery.

  DOI：

  10.1021/ja412520g

文献信息

• Synthesis of α,α’-linked penta- and septaheterocycles by tandem Suzuki coupling
  作者：Hadiqa Zafar、James T. Brewster、Christopher D. Wight、Matthew McVeigh、Axel Steinbrück、Vincent M. Lynch、Jonathan L. Sessler

  DOI：10.1142/s1088424618501080

  日期：2019.1

  The controlled synthesis of oligoaromatics can provide materials of wide utility. Here, we describe the preparation of higher order oligoheterocycles via a tandem Suzuki cross-coupling protocol. This method has allowed for the iterative construction of fluorescent [Formula: see text],[Formula: see text]-linked penta- and septaheterocyclic systems with modification of the terminal moiety allowing for fine-tuning of the emission features.

  低聚芳烃的可控合成可以提供用途广泛的材料。在此，我们介绍了通过串联铃木交叉偶联协议制备高阶寡杂环的方法。这种方法可以迭代构建荧光[式：见正文]、[式：见正文]连接的五环和七环系统，通过修饰末端分子可以对发射特征进行微调。