14-[4-(2-{2-[2-(4-tritylphenoxy)ethoxy]ethoxy}ethoxy)phenoxy]-6,9,12-trioxatetradecan-2-one ethylene acetal | 145839-37-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 14-[4-(2-{2-[2-(4-tritylphenoxy)ethoxy]ethoxy}ethoxy)phenoxy]-6,9,12-trioxatetradecan-2-one ethylene acetal
• 英文别名: 2-methyl-2-[3-[2-[2-[2-[4-[2-[2-[2-(4-tritylphenoxy)ethoxy]ethoxy]ethoxy]phenoxy]ethoxy]ethoxy]ethoxy]propyl]-1,3-dioxolane
• CAS: 145839-37-8
• 化学式: C₅₀H₆₀O₁₀
• 分子量: 821.02
• InChiKey: VBTHCJUDUWAOLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.53
• 重原子数：
  60.0
• 可旋转键数：
  29.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  92.3
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  、 14-[4-(2-{2-[2-(4-tritylphenoxy)ethoxy]ethoxy}ethoxy)phenoxy]-6,9,12-trioxatetradecan-2-one ethylene acetal 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 2-methyl-5-[2-[2-[2-(4-tritylphenoxy)ethoxy]ethoxy]ethoxy]-3-[2-[2-[2-[2-[4-[2-[2-[2-(4-tritylphenoxy)ethoxy]ethoxy]ethoxy]phenoxy]ethoxy]ethoxy]ethoxy]ethyl]-1H-indole
  参考文献：
  名称：

  Toward Controllable Molecular Shuttles

  摘要：

  AbstractA number of nanometer‐scale molecular assemblies, based on rotaxane‐type structures, have been synthesized by means of a template‐directed strategy from simple building blocks that, on account of the molecular recognition arising from the noncovalent interactions between them, are able to self‐assemble into potential molecular abacuses. In all the cases investigated, the π‐electron‐deficient tetracationic cyclophane cyclobis(paraquat‐p‐phenylene) is constrained mechanically around a dumbbell‐shaped component consisting of a linear polyether chain intercepted by at least two, if not three, π‐electron‐rich units and terminated at each end by blocking groups or stoppers. The development of an approach toward constructing these molecular abacuses, in which the tetracationic cyclophane is able to shuttle back and forth with respect to the dumbbell‐shaped component, begins with the self‐assembly of a [2]rotaxane consisting of two hydroquinone rings symmetrically positioned within a polyether chain terminated by triisopropylsilyl ether blocking groups. In this first so‐called molecular shuttle, the tetracationic cyclophane oscillates in a degenerate fashion between the two π‐electron‐rich hydroquinone rings. Replacement of one of the hydroquinone rings—or the insertion of another π‐electron‐rich ring system between the two hydroquinine rings—introduces the possibility of translational isomerism, a phenomenon that arises because of the different relative positions and populations of the tetracationic cyclophane with respect to the π‐donor sites on the dumbbell‐shaped component. In two subsequent [2]rotaxanes, one of the hydroquinone rings in the dumbbell‐shaped component is replaced, first by a p‐xylyl and then by an indole unit. Finally, a tetrathiafulvalene (TTF) unit is positioned between two hydroquinone rings in the dumbbell‐shaped component. Spectroscopic and electrochemical investigations carried out on these first‐generation molecular shuttles show that they could be developed as molecular switches.

  DOI：

  10.1002/chem.19970030719
• 作为产物：
  描述：

  1,4-bis-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)benzene 在 咪唑 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 sodium hydride 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 117.0h， 生成 14-[4-(2-{2-[2-(4-tritylphenoxy)ethoxy]ethoxy}ethoxy)phenoxy]-6,9,12-trioxatetradecan-2-one ethylene acetal
  参考文献：
  名称：

  Toward Controllable Molecular Shuttles

  摘要：

  AbstractA number of nanometer‐scale molecular assemblies, based on rotaxane‐type structures, have been synthesized by means of a template‐directed strategy from simple building blocks that, on account of the molecular recognition arising from the noncovalent interactions between them, are able to self‐assemble into potential molecular abacuses. In all the cases investigated, the π‐electron‐deficient tetracationic cyclophane cyclobis(paraquat‐p‐phenylene) is constrained mechanically around a dumbbell‐shaped component consisting of a linear polyether chain intercepted by at least two, if not three, π‐electron‐rich units and terminated at each end by blocking groups or stoppers. The development of an approach toward constructing these molecular abacuses, in which the tetracationic cyclophane is able to shuttle back and forth with respect to the dumbbell‐shaped component, begins with the self‐assembly of a [2]rotaxane consisting of two hydroquinone rings symmetrically positioned within a polyether chain terminated by triisopropylsilyl ether blocking groups. In this first so‐called molecular shuttle, the tetracationic cyclophane oscillates in a degenerate fashion between the two π‐electron‐rich hydroquinone rings. Replacement of one of the hydroquinone rings—or the insertion of another π‐electron‐rich ring system between the two hydroquinine rings—introduces the possibility of translational isomerism, a phenomenon that arises because of the different relative positions and populations of the tetracationic cyclophane with respect to the π‐donor sites on the dumbbell‐shaped component. In two subsequent [2]rotaxanes, one of the hydroquinone rings in the dumbbell‐shaped component is replaced, first by a p‐xylyl and then by an indole unit. Finally, a tetrathiafulvalene (TTF) unit is positioned between two hydroquinone rings in the dumbbell‐shaped component. Spectroscopic and electrochemical investigations carried out on these first‐generation molecular shuttles show that they could be developed as molecular switches.

  DOI：

  10.1002/chem.19970030719