1,5,-bis(2-(2-(2-(prop-2-ynyloxy)ethoxy)ethoxy)ethoxy)naphthalene | 912464-35-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,5,-bis(2-(2-(2-(prop-2-ynyloxy)ethoxy)ethoxy)ethoxy)naphthalene
• 英文别名: 1,5-bis[2-(2-{2-(2-propyne)ethoxy}ethoxy)ethoxy]naphthalene；1,5-Bis[2-[2-(2-prop-2-ynoxyethoxy)ethoxy]ethoxy]naphthalene；1,5-bis[2-[2-(2-prop-2-ynoxyethoxy)ethoxy]ethoxy]naphthalene
• CAS: 912464-35-8
• 化学式: C₂₈H₃₆O₈
• 分子量: 500.589
• InChiKey: NSCAOSDDZDVXPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  36
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,5,-bis(2-(2-(2-(prop-2-ynyloxy)ethoxy)ethoxy)ethoxy)naphthalene 、 cyclobis(paraquat-1,4-phenylene) tetrakis(hexafluorophosphate) 在 copper diacetate 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以21%的产率得到
  参考文献：
  名称：

  Cyclobis(paraquat-p-phenylene)-Based [2]Catenanes Prepared by Kinetically Controlled Reactions Involving Alkynes

  摘要：

  [GRAPHICS]Charged donor-acceptor [ 2]catenanes, in which the pi-accepting cyclobis(paraquat-p-phenylene) acts as a tetracationic template for the threading-followed-by- clipping of acyclic oligoethers, incorporating centrally a pi-donating 1,5-dioxynaphthalene ring system and terminated either by acetylene units or by acetylene and azide functions, are the products of copper-mediated Eglinton coupling and Huisgen 1,3-dipolar cycloaddition, respectively.

  DOI：

  10.1021/ol061864d
• 作为产物：
  描述：

  3-溴丙炔 、 1,5-bis[2-(2-(2-hydroxyethoxy)ethoxy)ethoxy]naphthalene 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 xylene 为溶剂， 反应 96.0h， 以52%的产率得到1,5,-bis(2-(2-(2-(prop-2-ynyloxy)ethoxy)ethoxy)ethoxy)naphthalene
  参考文献：
  名称：

  Cyclobis(paraquat-p-phenylene)-Based [2]Catenanes Prepared by Kinetically Controlled Reactions Involving Alkynes

  摘要：

  [GRAPHICS]Charged donor-acceptor [ 2]catenanes, in which the pi-accepting cyclobis(paraquat-p-phenylene) acts as a tetracationic template for the threading-followed-by- clipping of acyclic oligoethers, incorporating centrally a pi-donating 1,5-dioxynaphthalene ring system and terminated either by acetylene units or by acetylene and azide functions, are the products of copper-mediated Eglinton coupling and Huisgen 1,3-dipolar cycloaddition, respectively.

  DOI：

  10.1021/ol061864d

文献信息

• Structural and Co-conformational Effects of Alkyne-Derived Subunits in Charged Donor−Acceptor [2]Catenanes
  作者：Ognjen Š. Miljanić、William R. Dichtel、Saeed I. Khan、Shahab Mortezaei、James R. Heath、J. Fraser Stoddart

  DOI：10.1021/ja071319n

  日期：2007.7.1

  features in template-directed cyclizations of [2]pseudorotaxanes to give the [2]catenanes. Both reactions proceed well with precursors of appropriate oligoether chain lengths but fail when there are only three oxygen atoms in the oligoether chains between the DNP units and the reactive functional groups. The solid-state structures of the donor-acceptor [2]catenanes confirm their mechanically interlocked nature

  已经合成了四种供体 - 受体 [2] 链烷烃，其中环双（百草枯-对亚苯基）（CBPQT4+）作为接受π 电子的环烷和含有 1,5-二氧萘（DNP）的大环聚醚作为π 电子供体环在温和条件下，在合成的最后步骤中采用 Cu+ 催化的 Huisgen 1,3-偶极环加成和 Cu2+ 介导的 Eglinton 偶联。带有末端炔烃或叠氮化物的低聚醚链被用作 [2] 假轮烷的模板导向环化以得到 [2] 链烷烃的关键结构特征。两种反应都可以使用适当的低聚醚链长度的前体进行，但当低聚醚链中 DNP 单元和反应性官能团之间只有三个氧原子时，反应就会失败。供体-受体 [2] 链的固态结构证实了它们的机械互锁性质，通过 [pi...pi]、[CH...pi] 和 [CH...Omicron] 相互作用和点到 1,3-丁二炔和 1,2,3-三唑亚基与 CBPQT4+ 环的联吡啶单元之一之间的次级非共价接触。这些接触的特征在于内联吡啶环系统和
• A One-Pot Synthesis of Constitutionally Unsymmetrical Rotaxanes Using Sequential CuI-Catalyzed Azide–Alkyne Cycloadditions
  作者：Jason M. Spruell、William R. Dichtel、James R. Heath、J. Fraser Stoddart

  DOI：10.1002/chem.200800067

  日期：2008.5.9

  A one-pot sequential Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) strategy is presented for the synthesis of constitutionally unsymmetrical cyclobis(paraquat-p-phenylene)-based rotaxanes in good yields from simple starting materials. The methodology consists of performing multiple CuAAC reactions to stopper a pseudorotaxane in a stepwise manner, the order of which is controlled through silyl-protection

  提出了一锅顺序Cu（I）催化的叠氮化物-炔烃环加成（CuAAC）策略，用于从简单的起始原料以高收率合成结构不对称的基于环双（百草枯-对苯撑）的轮烷。该方法包括逐步进行多个CuAAC反应以终止假轮烷，其顺序通过末端炔基的甲硅烷基保护和Ag（I）催化的脱保护作用来控制。两亲性支链[4]轮烷的合成突出了该方法。该方法提高了访问越来越复杂的机械互锁化合物以在设备中用作复杂和功能性分子机械的能力。
• Syntheses and Dynamics of Donor−Acceptor [2]Catenanes in Water
  作者：Lei Fang、Subhadeep Basu、Chi-Hau Sue、Albert C. Fahrenbach、J. Fraser Stoddart

  DOI：10.1021/ja1087562

  日期：2011.1.26

  subset of mechanically interlocked molecules, namely, donor-acceptor [2]catenanes, have been produced in aqueous solutions in good yields from readily available precursors. The catenations are templated by strong hydrophobic and [π···π] stacking interactions, which serve to assemble the corresponding supramolecular precursors, prior to postassembly covalent modification. Dynamic (1)H NMR spectroscopic

  机械互锁分子的一个子集，即供体 - 受体 [2] 链，已经在水溶液中从容易获得的前体以良好的产率生产。在组装后共价修饰之前，通过强疏水性和[π...π] 堆积相互作用对链进行模板化，其用于组装相应的超分子前体。对这些 [2] 链烷之一进行的动态 (1) H NMR 光谱研究表明，丁二炔-三甘醇链的旋转运动以极低的活化焓发生，但在水中具有更高的负活化熵，相比之下有机溶剂。
• Cyclobis(paraquat-<i>p</i>-phenylene)-Based [2]Catenanes Prepared by Kinetically Controlled Reactions Involving Alkynes
  作者：Ognjen Š. Miljanić、William R. Dichtel、Shahab Mortezaei、J. Fraser Stoddart

  DOI：10.1021/ol061864d

  日期：2006.10.1

  [GRAPHICS]Charged donor-acceptor [ 2]catenanes, in which the pi-accepting cyclobis(paraquat-p-phenylene) acts as a tetracationic template for the threading-followed-by- clipping of acyclic oligoethers, incorporating centrally a pi-donating 1,5-dioxynaphthalene ring system and terminated either by acetylene units or by acetylene and azide functions, are the products of copper-mediated Eglinton coupling and Huisgen 1,3-dipolar cycloaddition, respectively.