1,11-Bis(1-naphthoxy-5-hydroxy)-3,6,9-trioxaundecan | 116059-02-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,11-Bis(1-naphthoxy-5-hydroxy)-3,6,9-trioxaundecan
• 英文别名: 5-[2-[2-[2-[2-(5-hydroxynaphthalen-1-yl)oxyethoxy]ethoxy]ethoxy]ethoxy]naphthalen-1-ol
• CAS: 116059-02-0
• 化学式: C₂₈H₃₀O₇
• 分子量: 478.542
• InChiKey: GTDLWCZUBLOIMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  35.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  86.61
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1,11-Bis(1-naphthoxy-5-hydroxy)-3,6,9-trioxaundecan 在 air 、 sodium hydride 、 copper(l) chloride 、 copper dichloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 168.0h， 生成 [2]-{[cyclobis(1,4,5,8-naphthalenetetracarboxylic diimide-hexa-2,4-diyne)](bis(1,5-naphtho)-38-crown-10)}-catenane
  参考文献：
  名称：

  Synthesis, Structure and Photophysics of Neutral π-Associated [2]Catenanes

  摘要：

  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.

  DOI：

  10.1002/(sici)1521-3765(19980416)4:4<608::aid-chem608>3.0.co;2-c
• 作为产物：
  描述：

  四乙二醇二对甲苯磺酸酯 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 1,11-Bis(1-naphthoxy-5-hydroxy)-3,6,9-trioxaundecan
  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

• Self-assembly of a novel series of hetero-duplexes driven by donor–acceptor interaction
  作者：Qi-Zhong Zhou、Mu-Xin Jia、Xue-Bin Shao、Li-Zhu Wu、Xi-Kui Jiang、Zhan-Ting Li、Guang-Ju Chen

  DOI：10.1016/j.tet.2005.05.039

  日期：2005.7

  The self-assembly of a novel series of donor-acceptor interaction-driven artificial hetero-duplexes in organic media has been described. Four linear compounds 1a-1d, bearing two to five electron rich 1,5-dioxynaphthalene units connected by the tetra(ethylene glycol) linker, respectively, have been prepared and used as donors, while eight compounds 2a-2d, 13-16, bearing one to four electron deficient pyromellitic diimide, 1,4,5,8-naphthalene-tetracarboxydiimide, or perylene-3,4,9,10-tetracarboxydiimide units, respectively, have been used as acceptors. The structure of the hetero-duplexes has been characterized by the H-1 NMR, UV-vis spectroscopy and vapor pressure osmometry. It is revealed that the binding stability of the duplexes vary greatly, depending on the length and structure of the monomers and also the solvent, and hetero-duplex 1d(.)2d displays a maximum association constant of ca. 1.0 x 10(4) m(-1) in chloroform. (c) 2005 Elsevier Ltd. All rights reserved.
• Oligocatenanes Made to Order¹
  作者：David B. Amabilino、Peter R. Ashton、Vincenzo Balzani、Sue E. Boyd、Alberto Credi、Ju Young Lee、Stephan Menzer、J. Fraser Stoddart、Margherita Venturi、David J. Williams

  DOI：10.1021/ja9720873

  日期：1998.5.1

  The construction of catenanes, comprised of between two and seven interlocked rings, has been achieved. Two tris-1,5-naphtho-57-crown-15 macrocycles template the formation of cyclobis(paraquat-4,4'-biphenylene) to give a [3]catenane, which acts as a template for the construction of one and then another cyclobis(paraquat-p-phenylene) to give a [4]- and [5]catenane (Olympiadane). When high pressure was used in these templated syntheses, a [6]- and [7]catenane, as well as a [5]catenane that is topologically isomeric with Olympiadane, were also obtained. X-ray analyses of the [3]-, [5]-, and [7]catenanes reveal an optimum use of electrostatic, pi-pi stacking, [C-H ...pi] interactions, and [C-H ... O] hydrogen bonds in the organization of the component rings within the molecules. Noteworthy in the [7]catenane structure is the location of four of the PF6- anions within voids present in the 20(+) ion. Temperature-dependent H-1 NMR spectroscopic studies and electrochemical investigations have revealed the dynamic and redox behavior of these catenanes in solution.
• Amabilino, David B.; Ashton, Peter R.; Reder, Anatoli S., Angewandte Chemie, 1994, vol. 106, # 12, p. 1316 - 1319
  作者：Amabilino, David B.、Ashton, Peter R.、Reder, Anatoli S.、Spencer, Neil、Stoddart, J. Fraser

  DOI：——

  日期：——