1,11-bis-(5'-benzyloxynaphtoxy)-3,6,9-trioxaundecane | 116059-01-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,11-bis-(5'-benzyloxynaphtoxy)-3,6,9-trioxaundecane
• 英文别名: 1-phenylmethoxy-5-[2-[2-[2-[2-(5-phenylmethoxynaphthalen-1-yl)oxyethoxy]ethoxy]ethoxy]ethoxy]naphthalene
• CAS: 116059-01-9
• 化学式: C₄₂H₄₂O₇
• 分子量: 658.791
• InChiKey: XPSBSEYKDNLOLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.66
• 重原子数：
  49.0
• 可旋转键数：
  20.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  64.61
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1,11-bis-(5'-benzyloxynaphtoxy)-3,6,9-trioxaundecane 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 为溶剂， 反应 72.0h， 生成 1,5-dinaphtho[38]crown-10
  参考文献：
  名称：

  大环聚醚与两个二苯并氧萘残基络合制敌草快和百草枯

  摘要：

  NMR光谱和FAB质谱表明，结合有两个1,5-二萘单元的38-crown-10（1 / 5DN38C10）和35-crown-9（1 / 5DN35C9）醚与百草枯形成1：1配合物[溶液中的PQT] 2+和Diquat [DQT] 2+指示剂。在固态下，[PQT.1 / 5DN38C10] 2+络合物通过萘环和联吡啶鎓环之间的面对面（π/π电荷转移）相互作用而稳定，而自由的1 / 5DN35C9受体具有经典的边缘两个萘环之间的表面相互作用（Hδ+ /π静电）。

  DOI：

  10.1016/s0040-4039(01)91375-9
• 作为产物：
  描述：

  溴甲苯 在 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 1,11-bis-(5'-benzyloxynaphtoxy)-3,6,9-trioxaundecane
  参考文献：
  名称：

  大环聚醚与两个二苯并氧萘残基络合制敌草快和百草枯

  摘要：

  NMR光谱和FAB质谱表明，结合有两个1,5-二萘单元的38-crown-10（1 / 5DN38C10）和35-crown-9（1 / 5DN35C9）醚与百草枯形成1：1配合物[溶液中的PQT] 2+和Diquat [DQT] 2+指示剂。在固态下，[PQT.1 / 5DN38C10] 2+络合物通过萘环和联吡啶鎓环之间的面对面（π/π电荷转移）相互作用而稳定，而自由的1 / 5DN35C9受体具有经典的边缘两个萘环之间的表面相互作用（Hδ+ /π静电）。

  DOI：

  10.1016/s0040-4039(01)91375-9

文献信息

• Synthesis, Structure and Photophysics of Neutral π-Associated [2]Catenanes
  作者：Darren G. Hamilton、John E. Davies、Luca Prodi、Jeremy K. M. Sanders

  DOI：10.1002/(sici)1521-3765(19980416)4:4<608::aid-chem608>3.0.co;2-c

  日期：1998.4.16

  The supramolecular utility of a neutral re-stacking system of aromatic donors and accepters is illustrated with the syntheses of three neutral [2]catenanes. These templated syntheses are based on the oxidative dimerisation of electron-deficient aromatic diimide derivatives, equipped with terminal acetylene functions, in the presence of a preformed crown macrocycle containing complementary electron-rich aromatic diethers. X-ray crystallographic study of one of the catenanes and a precatenane crown/diimide inclusion complex reveals the ordered donor-acceptor stacking responsible for templating the catenane syntheses and subsequently organising the packing of the interlocked molecules in the solid state. NMR investigation of the catenanes reveals a dominant dynamic process at room temperature involving the sweeping of the crown macrocycle around the periphery of the interlocked structures; NOESY exchange spectra reveal a higher-energy process involving the revolution of the crown macrocycle through the centre of the second ring. This combined dynamic picture has been used to support the observed photophysical behaviour. Room-temperature fluorescence of the catenanes is only partially quenched by neighbouring chromophores, implying some mobility in the constituent rings; for one of the catenanes fluorescence quenching data enables an estimate to be made of the ratio of translational isomers present in solution. In contrast, low-temperature (77 K) fluorescence is totally quenched as a consequence of freezing all dynamic movement. Collectively, the results presented in this work lend support to the assertion that the robust, neutral building blocks employed in the catenane syntheses are ideal vehicles for the development of complex [n]catenane syntheses.