16-bromo-2,5,8,11,14,19,22,25,28,31-decaoxa-tricyclo[30.2.2.2^15,18]octatriaconta-1(35),15(38),16,18(37),32(36),33-hexaene | 583040-67-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 16-bromo-2,5,8,11,14,19,22,25,28,31-decaoxa-tricyclo[30.2.2.2^15,18]octatriaconta-1(35),15(38),16,18(37),32(36),33-hexaene
• CAS: 583040-67-9
• 化学式: C₂₈H₃₉BrO₁₀
• 分子量: 615.516
• InChiKey: DLBQHQWKHGAXLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  39.0
• 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：

  16-bromo-2,5,8,11,14,19,22,25,28,31-decaoxa-tricyclo[30.2.2.2^15,18]octatriaconta-1(35),15(38),16,18(37),32(36),33-hexaene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide sodium hydroxide 、 二异丙胺 作用下， 以 苯 为溶剂， 反应 30.0h， 生成 16-ethynyl-2,5,8,11,14,19,22,25,28,31-decaoxa-tricyclo[30.2.2.2^15,18]octatriaconta-1(35),15(38),16,18(37),32(36),33-hexaene
  参考文献：
  名称：

  供体-受体相互作用驱动四氢键合氢二聚体的选择性重排。

  摘要：

  通过引入额外的供体-受体相互作用，已开发出一种通用方法来控制梅耶尔的AADD四重氢键均二聚体的选择性重排。因此，在其中一种供体组装单体1中，其中富电子的双（对亚苯基）-34-crown-10部分与氢键合部分连接，而在两种供体组装单体2和3中，合成并表征了分别结合有电子缺陷的均苯四甲酸二酰亚胺或萘二酰亚胺基团。1H NMR和2D-NOESY研究表明，所有这些化合物均以稳定的均二聚体形式存在于氯仿中。在氯仿中混合1当量1和1当量2导致形成异二聚体1.2，产率约为60％，由于1的双（对亚苯基）-34-crown-10部分与2的均苯四甲二酰亚胺基团之间发生了静电相互作用，因此通过混合1当量的1可以实现选择性形成异二聚体1.3（> 97％）在氯仿中具有3当量的1当量，这导致1的双（对亚苯基）-[34] crown-10部分与3的萘二酰亚胺基团之间的静电相互作用增强。异二聚体1.2和1.3的结构具有通过1

  DOI：

  10.1002/chem.200204513
• 作为产物：
  描述：

  溴羟基喹啉 、 1,4-bis[2-(2-(2-(2-toluene-p-sulfonylethoxy)ethoxy)ethoxy)ethoxy]benzene 在 sodium hydroxide 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以43%的产率得到16-bromo-2,5,8,11,14,19,22,25,28,31-decaoxa-tricyclo[30.2.2.2^15,18]octatriaconta-1(35),15(38),16,18(37),32(36),33-hexaene
  参考文献：
  名称：

  供体-受体相互作用驱动四氢键合氢二聚体的选择性重排。

  摘要：

  通过引入额外的供体-受体相互作用，已开发出一种通用方法来控制梅耶尔的AADD四重氢键均二聚体的选择性重排。因此，在其中一种供体组装单体1中，其中富电子的双（对亚苯基）-34-crown-10部分与氢键合部分连接，而在两种供体组装单体2和3中，合成并表征了分别结合有电子缺陷的均苯四甲酸二酰亚胺或萘二酰亚胺基团。1H NMR和2D-NOESY研究表明，所有这些化合物均以稳定的均二聚体形式存在于氯仿中。在氯仿中混合1当量1和1当量2导致形成异二聚体1.2，产率约为60％，由于1的双（对亚苯基）-34-crown-10部分与2的均苯四甲二酰亚胺基团之间发生了静电相互作用，因此通过混合1当量的1可以实现选择性形成异二聚体1.3（> 97％）在氯仿中具有3当量的1当量，这导致1的双（对亚苯基）-[34] crown-10部分与3的萘二酰亚胺基团之间的静电相互作用增强。异二聚体1.2和1.3的结构具有通过1

  DOI：

  10.1002/chem.200204513

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.
• Divalent Pseudorotaxane with Polarized Plug–Socket and Padlock Functions
  作者：Zhengliang Qian、Xin Li、Tao Yuan、Xinghua Huang、Qiaochun Wang、Hans Ågren、He Tian

  DOI：10.1021/acs.orglett.7b03867

  日期：2018.3.16

  A dual-pore structured host composed of one 24-crown-8 and one 34-crown-10, and a "U"-shaped guest consisting of two different recognition units, one dibenzylammonium and one viologen, were synthesized and bound 1:1 into a divalent pseudorotaxane P1. P1 can mimic the inserting and pulling out functions of a polarized plug-socket system under solvent driven stimulus and can also realize the locking and unlocking actions of a padlock under pH stimulus.
• Highly stable pseudo[2]rotaxanes co-driven by crown ether–ammonium and donor–acceptor interactions
  作者：Dai-Jun Feng、Xiao-Qiang Li、Xiao-Zhong Wang、Xi-Kui Jiang、Zhan-Ting Li

  DOI：10.1016/j.tet.2004.05.066

  日期：2004.7

  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.