2,5-bis(3-bromophenyl)furan | 362047-04-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 2,5-bis(3-bromophenyl)furan
• CAS: 362047-04-9
• 化学式: C₁₆H₁₀Br₂O
• 分子量: 378.063
• InChiKey: DMPRORNESAHQDU-UHFFFAOYSA-N

物化性质

• 熔点：
  130-134 °C
• 沸点：
  413.7±35.0 °C(Predicted)
• 密度：
  1.607±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,5-bis(3-bromophenyl)furan 在 N-甲基吡咯烷酮 、 盐酸 作用下， 以 乙醇 为溶剂， 反应 158.0h， 生成 2,5-bis[3-(2-imidazolinyl)phenyl]furan
  参考文献：
  名称：

  Inhibition of the HIV-1 rev–RRE complex formation by unfused aromatic cations

  摘要：

  RNA viruses cause a wide range of human diseases. Development of new agents to target such viruses is an active area of research. Towards this goal, a series of diphenylfuran cations as potential inhibitors of the Rev-RRE complex have been designed and synthesized. Analysis of the interaction of the diphenylfurans with RRE and TAR RNA model systems by gel shift assays indicates that they exhibit both sequence and structure-dependent binding modes. Our results show a strong interaction between the diphenylfuran ring system and RRE bases, while the TAR interactions are much weaker with the compounds that are the best inhibitors of Rev-RRE. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00344-8
• 作为产物：
  描述：

  1,4-bis(3-bromophenyl)butane-1,4-dione 在 硫酸 、 乙酸酐 作用下， 生成 2,5-bis(3-bromophenyl)furan
  参考文献：
  名称：

  Discovery of new G-quadruplex binding chemotypes

  摘要：

  我们报告了一种新颖的基于呋喃的低分子量化学类型，具有高G-四链体亲和力和强效的抗增殖活性。

  DOI：

  10.1039/c3cc48616h

文献信息

• Bending the bonds: unveiling halogen interactions in the elastic polymorph of 2,5-bis(3-bromophenyl)furan
  作者：Konrad Dyk、Vasyl Kinzhybalo、Yuriy Horak、Serhii Butenko、Miłosz Siczek、Daniel M. Kamiński

  DOI：10.1107/s1600576723010609

  日期：2024.2.1

  investigates the structural properties of 2,5-bis(3-bromophenyl)furan polymorphs, focusing on the halogen interactions and their influence on crystal mechanical properties. In this study, three different polymorphic modifications were obtained which crystallize in the orthorhombic system. Two of the polymorphs possess halogen interactions but only one exhibits elastic properties. Through X-ray diffraction

  本文研究了 2,5-双(3-溴苯基)呋喃多晶型物的结构性质，重点关注卤素相互作用及其对晶体力学性质的影响。在这项研究中，获得了三种不同的多晶型修饰，它们在斜方晶系中结晶。其中两种多晶型物具有卤素相互作用，但只有一种具有弹性。通过 X 射线衍射、晶体学分析和计算模型，揭​​示了复杂的溴基卤素相互作用及其对堆积排列和稳定性的影响。探索了这些相互作用和晶体特性（包括分子排列和分子间力）之间的相关性。了解这些关系对于材料设计和超分子化学至关重要，从而能够合理合成定制材料。
• Transition-Metal-Free Continuous-Flow Synthesis of 2,5-Diaryl Furans: Access to Medicinal Building Blocks and Optoelectronic Materials
  作者：Helena F. Grantham、Robert J. Lee、Grzegorz M. Wardas、Jai-Ram Mistry、Mark R. J. Elsegood、Iain A. Wright、Gareth J. Pritchard、Marc C. Kimber

  DOI：10.1021/acs.joc.3c02237

  日期：2024.1.5

  synthetic approach to 2,5-diarylfurans delivers several important furan building blocks used commonly in medicinal chemistry and as optoelectronic materials, including short-chain linearly conjugated furan oligomers. Consequently, we also complete a short study of the optical and electrochemical properties of a selection of these novel materials.

  提出了使用无过渡金属的条件将 1,3-二烯直接转化为有价值的 2,5-二芳基呋喃。通过对容易获得的 1,3-二烯采用简单的氧化脱水序列，制备了在药物和材料化学中常用的重要的 2,5-二芳基呋喃结构单元。氧化步骤是使用单线态氧实现的，并且使用Appel试剂在无金属条件和环境温度下将中间体内过氧化物脱水。值得注意的是，该序列可以简化为连续流，从而消除中间体（通常不稳定的内过氧化物）的分离。这使得 2,5-二芳基呋喃的分离产量显着提高（平均增加约 27%），同时还提高了安全性并减少了浪费。我们的 2,5-二芳基呋喃的无过渡金属合成方法提供了药物化学和光电材料中常用的几种重要的呋喃结构单元，包括短链线性共轭呋喃低聚物。因此，我们还完成了对这些新型材料的光学和电化学特性的简短研究。
• Structural Selectivity of Aromatic Diamidines
  作者：Jonathan B. Chaires、Jinsong Ren、Donald Hamelberg、Arvind Kumar、Vandna Pandya、David W. Boykin、W. David Wilson

  DOI：10.1021/jm049491e

  日期：2004.11.1

  Competition dialysis was used to study the interactions of 13 substituted aromatic diamidine compounds with 13 nucleic acid structures and sequences. The results show a striking selectivity of these compounds for the triplex structure poly dA:(poly dT)(2), a novel aspect of their interaction with nucleic acids not previously described. The triplex selectivity of selected compounds was confirmed by thermal denaturation studies. Triplex selectivity was found to be modulated by the location of amidine substiuents on the core phenyl-furan-phenyl ring scaffold. Molecular models were constructed to rationalize the triplex selectivity of DB359, the most selective compound in the series. Its triplex selectivity was found to arise from optimal ring stacking on base triplets, along with proper positioning of its amidine substituents to occupy the minor and the major-minor grooves of the triplex. New insights into the molecular recognition of nucleic acid structures emerged from these studies, adding to the list of available design principles for selectively targeting DNA and RNA.