三(1,5-萘)-57-冠-15 | 158394-28-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 三(1,5-萘)-57-冠-15
• 英文名称: tris(1,5-naphthalene)-57-crown-15
• 英文别名: 6,9,12,15,18,29,32,35,38,41,52,55,58,61,64-Pentadecaoxaheptacyclo[63.4.0.05,69.019,24.023,28.042,47.046,51]nonahexaconta-1(69),2,4,19,21,23,25,27,42,44,46,48,50,65,67-pentadecaene
• CAS: 158394-28-6
• 化学式: C₅₄H₆₆O₁₅
• 分子量: 955.109
• InChiKey: QMAXLIONURJYQK-UHFFFAOYSA-N

物化性质

• 沸点：
  1047.1±65.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  69
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  4,4'-二溴甲基联苯 、 1,1'-[4,4'-biphenylenedimethylene]bis-4,4'-bipyridinium bis(hexafluorophosphate) 、 三(1,5-萘)-57-冠-15 在 ammonium hexafluorophosphate 、 水 、 丙酮 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 240.0h， 以6%的产率得到
  参考文献：
  名称：

  Amabilino, David B.; Ashton, Peter R.; Reder, Anatoli S., Angewandte Chemie, 1994, vol. 106, # 12, p. 1316 - 1319

  摘要：

  DOI：
• 作为产物：
  描述：

  四乙二醇二对甲苯磺酸酯 在 potassium carbonate 、 caesium carbonate 、 cesium 4-methylbenzenesulfonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 三(1,5-萘)-57-冠-15
  参考文献：
  名称：

  Oligocatenanes Made to Order¹

  摘要：

  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.

  DOI：

  10.1021/ja9720873

文献信息

• The solid-state self-organisation of a self-assembled [2]catenane
  作者：David B. Amabilino、Peter R. Ashton、J. Fraser Stoddart、Stephan Menzer、David J. Williams

  DOI：10.1039/c39940002475

  日期：——

  The reluctance of a [2]catanane, comprised cf macrocycles incorporating π-donors and π-acceptors, to be catenated further to form a [3]catenane may be explained by the molecular arrangement revealed in the solid-state structure of the [2]catenane, which shows all aromatic units to be involved in intramolecularπ–π stacking interactions; moreover, the molecules self-organise in the solid-state to form a quilt-like two-dimensional array by virtue of intermolecularπ–π stacking interactions.

  由包含 π-供体和 π-受体的大环组成的 [2]catanane 不愿意进一步连接形成 [3]catanane 可以通过 [2] 固态结构中揭示的分子排列来解释。 ]catenane，显示所有芳香族单元都参与分子内π-π堆积相互作用；此外，分子在固态下通过分子间π-π堆积相互作用自组织形成被子状的二维阵列。
• Template-Directed Syntheses, Spectroscopic Properties, and Electrochemical Behavior of [n]Catenanes
  作者：Peter R. Ashton、Virna Baldoni、Vincenzo Balzani、Christian G. Claessens、Alberto Credi、H. D. Andreas Hoffmann、Françisco M. Raymo、J. Fraser Stoddart、Margherita Venturi、Andrew J. P. White、David J. Williams

  DOI：10.1002/1099-0690(200004)2000:7<1121::aid-ejoc1121>3.0.co;2-3

  日期：2000.4

  Catenanes composed of two, three, five, or seven interlocked macrocycles have been synthesized in yields ranging from 1 to 30%. Their template-directed syntheses rely on a series of cooperative noncovalent bonding interactions between π-electron rich 1,5-dioxynaphthalene ring systems and π-electron deficient bipyridinium units which are incorporated within the macrocyclic components. The interlocked

  合成了由两个，三个，五个或七个互锁的大环组成的链烯，产率为1％至30％。它们的模板指导的合成依赖于在大环组分中掺入的富含π电子的1,5-二氧萘环系统与缺乏π电子的联吡啶鎓单元之间的一系列协作性非共价键相互作用。单晶X射线分析清楚地证明了与[3]邻苯二酚之一相关的互锁结构，该结构还揭示了通过分子间[π ···π]相互作用。通过液体次级离子，基质辅助激光解吸电离/飞行时间和/或电喷雾质谱法确定每个链烷烃的互锁组分数。已经研究了大环组分和链烷的吸收光谱，发射光谱和电化学性质。已经发现了两种电荷转移吸收带（在含有电子供体和电子受体单元的环烷中是分子内的，在链烯中是内部的）。这种电荷转移激发态负责环烷中潜在的荧光单元以及连环中冠醚的猝灭。电化学行为也证明了电荷转移电子相互作用。
• 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：——