4-[2-[2-[2-(2-bromo-ethoxy)-ethoxy]-ethoxy]-ethoxy]-phenyl benzyl ether | 744251-98-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-[2-[2-[2-(2-bromo-ethoxy)-ethoxy]-ethoxy]-ethoxy]-phenyl benzyl ether
• 英文别名: 4-[2-[2-[2-(2-bromoethoxy)ethoxy]ethoxy]ethoxy]phenyl benzyl ether
• CAS: 744251-98-7
• 化学式: C₂₁H₂₇BrO₅
• 分子量: 439.346
• InChiKey: HICICDNJPLQLBL-UHFFFAOYSA-N

物化性质

• 沸点：
  526.8±50.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  27.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-[2-[2-[2-(2-bromo-ethoxy)-ethoxy]-ethoxy]-ethoxy]-phenyl benzyl ether 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 8.0h， 以98%的产率得到4-(2-{2-[2-(2-bromoethoxy)ethoxy]ethoxy}ethoxy)phenol
  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
• 作为产物：
  描述：

  1-溴-2-(2-(2-(2-溴乙氧基)乙氧基)乙氧基)乙烷 、 4-苄氧基苯酚 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 36.0h， 以40%的产率得到4-[2-[2-[2-(2-bromo-ethoxy)-ethoxy]-ethoxy]-ethoxy]-phenyl benzyl ether
  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

文献信息

• Donor–acceptor interaction-mediated arrangement of hydrogen bonded dimers
  作者：Xiao-Qiang Li、Dai-Jun Feng、Xi-Kui Jiang、Zhan-Ting Li

  DOI：10.1016/j.tet.2004.06.104

  日期：2004.9

  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.