1,17-bis(4-hydroxyphenoxy)-3,6,9,12,15-pentaoxaheptadecane | 168191-28-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1,17-bis(4-hydroxyphenoxy)-3,6,9,12,15-pentaoxaheptadecane
• CAS: 168191-28-4
• 化学式: C₂₄H₃₄O₉
• 分子量: 466.529
• InChiKey: LCKZMKABDSRXNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.64
• 重原子数：
  33.0
• 可旋转键数：
  20.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105.07
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  六乙二醇双-P二对甲苯磺酸 、 1,17-bis(4-hydroxyphenoxy)-3,6,9,12,15-pentaoxaheptadecane 在 四丁基碘化铵 、 caesium carbonate 、 cesium 4-methylbenzenesulfonate 作用下， 生成 1,4,7,10,13,16,19,26,29,32,35,38,41,44-tetradecaoxa<19,19>paracyclophane
  参考文献：
  名称：

  Molecular Meccano. 2. Self-Assembly of [n]Catenanes

  摘要：

  The mutual molecular recognition between different: structural components in large rings has led to the template-directed synthesis of a wide range of catenanes composed of from two to five interlocked rings, The molecular self-assembly processes rely upon the recognition between (i) pi-electron rich and pi-electron deficient aromatic units and (ii) hydrogen bond donors and accepters, in the different components. In order to increase Our knowledge of the factors involved in such molecular self-assembly processes, a homologous series of [2]catenanes has been constructed using macrocyclic polyethers of the bis(p-phenylene)-(3n+4)-crown-n (n = 9-14) type as templates for the formation of the tetracationic cyclophane, cyclobis(paraquat-p-phenylene). Increasing the size of the tetracationic cyclophane to cyclobis(paraquat-4,4'-bitolyl) allows the simultaneous entrapment of two hydroquinone ring-containing macrocyclic polyethers affording a series of [3]catenanes, and one [4]catenane incorporating a cyclic dimer of the expanded cyclophane and three bis(p-phenylene)-34-crown-10 components. By analogy; increasing the number of hydroquinone rings in the macrocyclic polyether permits the self-assembly of more than one tetracationic cyclophane around the templates present in the macrocyclic polyether. In this context, the template-directed synthesis of two [3]catenanes, incorporating two cyclobis(paraquat-p-phenylene) components and either (i) tris(p-phenylene)51-crown-15 or (ii) tetrakis (p-phenylene)-68-crown-20, has been achieved and is reported. A combination of these two approaches has led to the successful self-assembly, in two steps, of a linear [4]catenane, together with a small amount of a [5]catenane: The creation of these intricate molecular compounds lends support to the contention that self-assembly is a viable paradigm for the construction of nanometer-scale molecular architectures incorporating a selection of simple components.

  DOI：

  10.1021/ja00109a011
• 作为产物：
  描述：

  1,17-bis<4-(benzyloxy)phenoxy>-3,6,9,12,15-pentaoxaheptadecane 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 氯仿 为溶剂， 以98%的产率得到1,17-bis(4-hydroxyphenoxy)-3,6,9,12,15-pentaoxaheptadecane
  参考文献：
  名称：

  Molecular Meccano. 2. Self-Assembly of [n]Catenanes

  摘要：

  The mutual molecular recognition between different: structural components in large rings has led to the template-directed synthesis of a wide range of catenanes composed of from two to five interlocked rings, The molecular self-assembly processes rely upon the recognition between (i) pi-electron rich and pi-electron deficient aromatic units and (ii) hydrogen bond donors and accepters, in the different components. In order to increase Our knowledge of the factors involved in such molecular self-assembly processes, a homologous series of [2]catenanes has been constructed using macrocyclic polyethers of the bis(p-phenylene)-(3n+4)-crown-n (n = 9-14) type as templates for the formation of the tetracationic cyclophane, cyclobis(paraquat-p-phenylene). Increasing the size of the tetracationic cyclophane to cyclobis(paraquat-4,4'-bitolyl) allows the simultaneous entrapment of two hydroquinone ring-containing macrocyclic polyethers affording a series of [3]catenanes, and one [4]catenane incorporating a cyclic dimer of the expanded cyclophane and three bis(p-phenylene)-34-crown-10 components. By analogy; increasing the number of hydroquinone rings in the macrocyclic polyether permits the self-assembly of more than one tetracationic cyclophane around the templates present in the macrocyclic polyether. In this context, the template-directed synthesis of two [3]catenanes, incorporating two cyclobis(paraquat-p-phenylene) components and either (i) tris(p-phenylene)51-crown-15 or (ii) tetrakis (p-phenylene)-68-crown-20, has been achieved and is reported. A combination of these two approaches has led to the successful self-assembly, in two steps, of a linear [4]catenane, together with a small amount of a [5]catenane: The creation of these intricate molecular compounds lends support to the contention that self-assembly is a viable paradigm for the construction of nanometer-scale molecular architectures incorporating a selection of simple components.

  DOI：

  10.1021/ja00109a011