1,4,7,10,13,20,23,26,29,32-decaoxa<13>paracyclo<13>(1,5)-naphthalenophane | 153530-56-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,4,7,10,13,20,23,26,29,32-decaoxa<13>paracyclo<13>(1,5)-naphthalenophane
• 英文别名: 1,5-NPPP36C10；1,5-dinaphthoparaphenylene[36]crown-10；1,5-naphthoparaphenylene[36]crown-10；2,5,8,11,14,25,28,31,34,37-Decaoxatetracyclo[36.2.2.015,20.019,24]dotetraconta-1(41),15,17,19,21,23,38(42),39-octaene
• CAS: 153530-56-4
• 化学式: C₃₂H₄₂O₁₀
• 分子量: 586.679
• InChiKey: UIYIGOCQSGAPHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  42
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  92.3
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,2-二(4-吡啶基)乙烯 、 1,1'-bis(4-(bromomethyl)benzyl)-4,4'-bipyridine-1,1'-diium bis(hexafluorophosphate) 、 1,4,7,10,13,20,23,26,29,32-decaoxa<13>paracyclo<13>(1,5)-naphthalenophane 在 ammonium hexafluorophosphate 、 水 作用下， 生成 <<2>-<1,4,7,10,13,20,23,26,29,32-decaoxa<13>paracyclo<13>(1.5)-naphthalenophane>-<(E)-6,17,26,37-tetraazonia<2.1.1.0.1.1>paracyclo-1-phene>catenane> tetrakis(hexafluorophospate)
  参考文献：
  名称：

  Ashton, Peter R.; Perez-Garcia, Lluisa; Stoddart, J. Fraser, Angewandte Chemie, 1995, vol. 107, # 5, p. 607 - 610

  摘要：

  DOI：
• 作为产物：
  描述：

  对苯二酚 、 1,5-bis[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]naphthalene bis(4-methylbenzenesulfonate) 在 caesium carbonate 、 cesium 4-methylbenzenesulfonate 作用下， 以 乙腈 为溶剂， 反应 120.0h， 以32%的产率得到1,4,7,10,13,20,23,26,29,32-decaoxa<13>paracyclo<13>(1,5)-naphthalenophane
  参考文献：
  名称：

  Ashton, Peter R.; Ballardini, Roberto; Balzani, Vincenzo, Journal of the American Chemical Society, 1995, vol. 117, # 45, p. 11171 - 11197

  摘要：

  DOI：

文献信息

• Dynamic Chirality: Keen Selection in the Face of Stereochemical Diversity in Mechanically Bonded Compounds
  作者：Hsian-Rong Tseng、Scott A. Vignon、Paul C. Celestre、J. Fraser Stoddart、Andrew J. P. White、David J. Williams

  DOI：10.1002/chem.200390057

  日期：2003.1.20

  on all three [2]catenanes and two of the three [3]catenanes reveals co-conformational and stereochemical preferences that are stark and pronounced. Both the [3]catenanes crystallize as mixtures of diastereoisomers on account of the axial chirality associated with the picolinium units in the solid state. Dynamic (1)H NMR spectroscopy is employed to probe in solution the relative energy barriers for rotations

  使用双对亚苯基-[34] crown-10（BPP34C10），1,5-二萘并对亚苯基-[36] crown-10（1 / 5NPPP36C10）和1,5-二萘并-[38] crown-10进行模板指导的合成描述了三[2]个邻苯二酚中作为模板的（1 / 5DNP38C10），其中环双（百草枯-对亚苯基）中的两个联吡啶鎓单元之一被联吡啶鎓取代。包含[2]儿茶酚的粗制反应混合物全部含有稍微更多的同源[3]儿茶酚，其中“二聚”八阳离子环烷具有冠状醚大环，该冠醚大环包围交替的联吡啶鎓单元，而联吡啶吡啶鎓单元完全不受约束。对所有三个[2]邻苯二酚和三个[3]邻苯二酚中的两个进行X射线晶体学分析，发现其共构象和立体化学偏爱显着而明显。由于与固态的吡啶鎓单元相关的轴向手性，这两种[3]邻苯二酚均结晶为非对映异构体的混合物。动态（1）H NMR光谱用于在溶液中探测[2]邻苯二甲四阳离子环庚烷组分中亚苯基和
• The Slipping Approach to Self-Assembling [<i>n</i>]Rotaxanes
  作者：Masumi Asakawa、Peter R. Ashton、Roberto Ballardini、Vincenzo Balzani、Martin Bělohradský、Maria Teresa Gandolfi、Oldrich Kocian、Luca Prodi、Françisco M. Raymo、J. Fraser Stoddart、Margherita Venturi

  DOI：10.1021/ja961817o

  日期：1997.1.1

  A synthetic approach-namely slippage-to self-assembling [n]rotaxanes incorporating pi-electron deficient bipyridinium-based dumbbell-shaped components and pi-electron-rich hydroquinone- and/or dioxynaphthalene-based macrocyclic polyether components has been developed. The kinetics of rotaxane formation by the slipping procedure were investigated by absorption UV-visible and H-1-NMR spectroscopies in a range of temperatures and solvents, varying systematically the size of both the stoppers and the macrocyclic components. As expected, the rate constants for these processes are affected by the size complementarity between macrocycles and stoppers. Furthermore, the enthalpic and entropic contributions to the free energies of activation associated with the slippage and the effect of solvent polarity upon the outcome of these processes have been evaluated. In addition, the spectroscopic and electrochemical properties of some of the rotaxanes are presented and discussed with reference to the properties of their chromophoric and electroactive units.
• Liquid-Assisted One-Pot Mechanosynthesis and Properties of Neutral Donor–Acceptor [2]Rotaxanes
  作者：Hai-Gen Li、Guan-Wu Wang

  DOI：10.1021/acs.joc.7b00912

  日期：2017.6.16

  An efficient liquid-assisted one-pot two-step synthesis of neutral donor-acceptor,[2]rotaxanes has been successfully realized under high-speed vibration milling conditions, by taking advantage of the donor acceptor interaction between the electron-rich naphthalene unit of a macrocyclic polyether and the electron-deficient naphthalene diimide unit of a thread component for the threading process and click reaction as the stoppering process. The present method provides a powerful, fast, and environmentally benign alternative to traditional solvent-based approaches due to its notable advantages such as very small amount of solvent, no external heating, shorter reaction time, and higher yield. In addition, the charge-transfer interaction and electrochemically induced shuttling of the synthesized neutral donor-acceptor [2]rotaxanes have been demonstrated.
• Kinetic and Thermodynamic Effects in the Self‐Assembly of [3]Catenanes in the Solution and Solid States
  作者：David B. Amabilino、Peter R. Ashton、J. Fraser Stoddart、A. J. P. White、David J. Williams

  DOI：10.1002/(sici)1521-3765(19980310)4:3<460::aid-chem460>3.0.co;2-#

  日期：1998.3.10