1,4,7,10,13,20,23,26,29,32-decaoxa-15,34-dibromo[13,13]paracyclophane | 773891-82-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4,7,10,13,20,23,26,29,32-decaoxa-15,34-dibromo[13,13]paracyclophane
• 英文别名: 1,4,7,13,20,23,26,29,32-decaoxa-15,34-dibromo[13,13]paracyclophane
• CAS: 773891-82-0
• 化学式: C₂₈H₃₈Br₂O₁₀
• 分子量: 694.412
• InChiKey: HOGSFBOSSDCDAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  40.0
• 可旋转键数：
  0.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  92.3
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1,4,7,10,13,20,23,26,29,32-decaoxa-15,34-dibromo[13,13]paracyclophane 在 四(三苯基膦)钯 四氢吡咯 、 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成
  参考文献：
  名称：

  Donor–acceptor interaction-mediated arrangement of hydrogen bonded dimers

  摘要：

  The donor-acceptor interaction-driven supramolecular arrangement of a new series of quadruply hydrogen-bonded homo- and heterodimers have been investigated in chloroform with H-1 NMR and UV-Vis spectroscopy. Two kinds of structurally complementary monomers have been prepared. Monomers 3 and 4 are incorporated with one ureidopyrimidone unit and one electron deficient pyromellitic diimide (PDI) or naphthalene diimide (NDI) unit, respectively, monomers 5 and 6 are incorporated with two ureidopyrimidone units and one PDI or NDI unit, respectively, whereas monomers 7 and 8 consist of one electron rich bis-p-phenylene[34]crown-10 unit and one or two 2,7-diamido-1,6-naphthyridine units, respectively. Compounds 3 and 4 exist exclusively as homodimers, respectively. Adding 1 equiv. of 7 to the solution of 3.3 and 4.4 induced them to partially or fully dissociate to produce heterodimers 3.7 and 4.7 due to intermolecular donor-acceptor interaction and the formation of a new binding mode between the ureidopyrimidone of 3 or 4 and the 2,7-diamido-1,6-naphthyridine unit of 7. Both 5 and 6 exist as cyclic monomer and dimer in chloroform. Adding 1 equiv. of 8 to the solution of 5 or 6 in chloroform caused all the cyclic dimer and most of the cyclic monomer to de-cyclize to form new heterodimers 5.8 and 6.8, respectively. H-1 NMR and UV-vis study revealed that heterodimer 5.8 has a structure in which the PDI of 5 is not threaded through the cavity of the bis-p-phenylene [34] crown-10 unit of 8. In contrast, in addition to the heterodimer similar to 5.8, about 40% of heterodimer 6.8 is generated, in which the PDI of 6 is threaded through the cavity of the bis-p-phenylene[3]crown-10 unit of 8 due to the increased donor-acceptor interaction between NDI and bis-p-phenylene [34] crown-10. Steric hindrance and mismatching of the hydrogen bonding moiety play important roles in the arrangement of the new homo- and heterodimers. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.104
• 作为产物：
  描述：

  2-bromo-4-[2-[2-[2-(2-bromo-ethoxy)-ethoxy]-ethoxy]-ethoxy]phenol 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以56%的产率得到1,4,7,10,13,20,23,26,29,32-decaoxa-15,34-dibromo[13,13]paracyclophane
  参考文献：
  名称：

  Highly stable pseudo[2]rotaxanes co-driven by crown ether–ammonium and donor–acceptor interactions

  摘要：

  Bis-p-phenylene-34-crown-10 derivatives 1 and 2, bearing one and two dibenzo [24] crown-8 units, respectively, and 4,4'-dipyridinium derivatives of 3.3PF(6) and of 4.4PF(6), bearing one and two ammonium groups, respectively, have been synthesized from readily available starting materials. H-1 NMR and UV-vis studies reveal that in polar acetonitrile 1 binds 3.3PF6 to produce pseudo [2]rotaxane 1.3.3PF(6) by making use of one donor-acceptor and one electrostatic interaction, whereas 2 binds 4-4PF(6) to form pseudo [2] rotaxane 2.4.4PF(6) through one donor-acceptor and two electrostatic interactions. The association constants of the two pseudorotaxanes have been determined by the UV-vis titration method to be 9.1 (+/-1.0) x 10(3) M-1 and 6.5 (+/-0.7) x 10(5) M-1, respectively. The high stability of the new pseudo [2]rotaxanes has been ascribed to the cooperative interaction of the two different non-covalent forces. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2004.05.066