3,7-bis(bromomethyl)dibenzofuran | 52084-44-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3,7-bis(bromomethyl)dibenzofuran
• CAS: 52084-44-3
• 化学式: C₁₄H₁₀Br₂O
• 分子量: 354.041
• InChiKey: LFFIYUKDUVRNPE-UHFFFAOYSA-N

物化性质

• 沸点：
  438.6±35.0 °C(Predicted)
• 密度：
  1.775±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.38
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  13.14
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4,4'-联吡啶 、 3,7-bis(bromomethyl)dibenzofuran 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  Molecular and Supramolecular Synthesis with Dibenzofuran-Containing Systems

  摘要：

  AbstractThe template‐directed syntheses of two new tetracationic cyclophanes, cyclobis(paraquat‐2,8‐dibenzofuran) and cyclobis(paraquat‐3,7‐dibenzofuran), incorporating dibenzofuran subunits has been accomplished. Initially, the cyclophanes were self‐assembled around a macrocyclic polyether template, bis‐p‐phenylene[34]crown‐10 (BPP34C10), to form catenanes: the mechanical bond order of the catenane formed determined the requisite “amacrocyclic” templates for synthesis of the free cyclophane. X‐ray crystallography shows that both of the cyclophanes possess rectangular covalent frameworks. Furthermore, these cyclophanes form self‐assembled tapes in the solid state, since the dibenzofuran moieties have a tendency to associate with each other through crossed ∞–∞ stacks. The dibenzofuran‐containing catenanes also form two‐dimensional supramolecular arrays in the solid state on account of extended ∞–∞ stacking interactions. In addition, the serendipitous discovery of a plerotopic tecton (consisting of a dibenzofuran nucleus covalently linked from the 2‐ and 8‐positions by methylene groups to 4,4′‐pyridylpyridinium (hydrogen bond acceptor) and protonated bipyridinium (hydrogen bond donor) units) has been made. The tecton dimerizes in the solid state to form a supramolecular macrocycle, since its complementary hydrogen bonding sites are oriented in a horseshoelike fashion by the 2,8‐disubstituted dibenzofuran unit. However, this superstructure is not retained in the 1:1 complex of the tecton with BPP34C10: cocrystallization of the tecton with this crown ether opens the macrocyclic two‐component supermolecule to afford a hydrogen‐bonded pseudopolyrotaxane.

  DOI：

  10.1002/chem.19970030720
• 作为产物：
  描述：

  3,7-二甲基二苯并呋喃 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 3.0h， 以43%的产率得到3,7-bis(bromomethyl)dibenzofuran
  参考文献：
  名称：

  Molecular and Supramolecular Synthesis with Dibenzofuran-Containing Systems

  摘要：

  AbstractThe template‐directed syntheses of two new tetracationic cyclophanes, cyclobis(paraquat‐2,8‐dibenzofuran) and cyclobis(paraquat‐3,7‐dibenzofuran), incorporating dibenzofuran subunits has been accomplished. Initially, the cyclophanes were self‐assembled around a macrocyclic polyether template, bis‐p‐phenylene[34]crown‐10 (BPP34C10), to form catenanes: the mechanical bond order of the catenane formed determined the requisite “amacrocyclic” templates for synthesis of the free cyclophane. X‐ray crystallography shows that both of the cyclophanes possess rectangular covalent frameworks. Furthermore, these cyclophanes form self‐assembled tapes in the solid state, since the dibenzofuran moieties have a tendency to associate with each other through crossed ∞–∞ stacks. The dibenzofuran‐containing catenanes also form two‐dimensional supramolecular arrays in the solid state on account of extended ∞–∞ stacking interactions. In addition, the serendipitous discovery of a plerotopic tecton (consisting of a dibenzofuran nucleus covalently linked from the 2‐ and 8‐positions by methylene groups to 4,4′‐pyridylpyridinium (hydrogen bond acceptor) and protonated bipyridinium (hydrogen bond donor) units) has been made. The tecton dimerizes in the solid state to form a supramolecular macrocycle, since its complementary hydrogen bonding sites are oriented in a horseshoelike fashion by the 2,8‐disubstituted dibenzofuran unit. However, this superstructure is not retained in the 1:1 complex of the tecton with BPP34C10: cocrystallization of the tecton with this crown ether opens the macrocyclic two‐component supermolecule to afford a hydrogen‐bonded pseudopolyrotaxane.

  DOI：

  10.1002/chem.19970030720

文献信息

• Self-Assembly and Self-Organization of Self-Recognizing Cyclophanes
  作者：Peter R. Ashton、Alexandre Chemin、Christian G. Claessens、Stephan Menzer、J. Fraser Stoddart、Andrew J. P. White、David J. Williams

  DOI：10.1002/(sici)1099-0690(199806)1998:6<969::aid-ejoc969>3.0.co;2-g

  日期：1998.6

  has been shown to pack as highly ordered two-dimensional, mosaic-like sheets in the solid state. Its dicationic precursor also forms extended π-π-stacked layers in the solid state. An analogous cyclophane – containing two π-electron-rich resorcinol rings in place of the two hydroquinone rings – forms, in the solid state, one-dimensional arrays wherein the component resorcinol rings interact through their

  分析了导致在各种基于联吡啶的分子组装和超分子阵列的晶体结构中观察到的堆积的不同贡献。展示了如何利用有助于这些分子和超分子固态排列的各种相互作用——静电、范德华力和 π-π 相互作用来设计一系列四阳离子环烷由于它们包含 π 电子供体和 π 电子受体，因此它们在固态中以高度有序的方式组织。概述了这些环芳烃的合成，并证明了自组装方法在其构造中的可调性。这些四阳离子环芳中的一种——包括富含 π 电子的氢醌环和缺乏 π 电子的双吡啶单元——已被证明在固态下以高度有序的二维马赛克状片状堆积。它的双阳离子前体还在固态下形成扩展的 π-π 堆叠层。一个类似的环烷——包含两个富含 π 电子的间苯二酚环代替两个氢醌环——在固态下形成一维阵列，其中组分间苯二酚环通过它们的平行 π-π 堆叠相互作用。还已经确定，上述四阳离子环芳中的第一个与二茂铁在溶液和固态形成 1:1 加合物。X 射线晶体学，在 1:1 加合物上进行，