5-Isocyanato-1,2,3-tris-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-benzene | 756900-71-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-Isocyanato-1,2,3-tris-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-benzene
• CAS: 756900-71-7
• 化学式: C₃₄H₅₉NO₁₆
• 分子量: 737.84
• InChiKey: ADHYNDKXVMEYRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  51.0
• 可旋转键数：
  40.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  167.88
• 氢给体数：
  0.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  5-Isocyanato-1,2,3-tris-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-benzene 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 {(3,4,5-tris{2-(2-{2-[2-methoxyethoxy]ethoxy}ethoxy)ethoxy})phenylureido}methanephosphonic acid
  参考文献：
  名称：

  Multicomponent Host−Guest Chemistry of Carboxylic Acid and Phosphonic Acid Based Guests with Dendritic Hosts:  An NMR Study

  摘要：

  A new way to analyze supramolecular dendritic architectures is reported by making use of C-13 NMR and P-31 NMR. Two ethylene glycol guest molecules have been synthesized containing a 13C labeled carboxylic acid headgroup (2) and a phosphonic acid headgroup (3). The binding of these guests to urea-adamantyl modified poly(propylene imine) dendrimers has been investigated with C-13 NMR and P-31 NMR next to 1D and 2D H-1 NMR techniques. Different amounts of guest 2 have been added to fifth generation dendrimer le, and the observed chemical shift values in C-13 NMR were fitted to a model that assumes 1:1 binding between guest and binding site. An association constant of 400 +/- 95 M-1 is obtained for guest 2 with 41 binding sites per dendrimer. When different amounts of phosphonic acid guest 3 are added to dendrimer le, two different signals are observed in P-31 NMR. Deconvolution gives the fractions of free and bound guest, resulting in an association constant of (4 3) x 104 M-1 and 61 1 binding sites. A statistical analysis shows that guest 2 forms a "polydisperse supramolecular aggregate", while guest 3 is able to form a "monodisperse supramolecular aggregate" when the amount of guest is high enough. The NMR results are compared with dynamic light scattering experiments, and a remarkable agreement is found. Phosphonic acid guest 3 is able to exchange with guest 2, which is in agreement with the obtained association constants, and shows that these techniques can be used to analyze multicomponent dendritic aggregates.

  DOI：

  10.1021/ja052074m
• 作为产物：
  描述：

  3,4,5-Tris-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-benzoyl azide 以 甲苯 为溶剂， 反应 2.5h， 生成 5-Isocyanato-1,2,3-tris-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-benzene
  参考文献：
  名称：

  Multicomponent Host−Guest Chemistry of Carboxylic Acid and Phosphonic Acid Based Guests with Dendritic Hosts:  An NMR Study

  摘要：

  A new way to analyze supramolecular dendritic architectures is reported by making use of C-13 NMR and P-31 NMR. Two ethylene glycol guest molecules have been synthesized containing a 13C labeled carboxylic acid headgroup (2) and a phosphonic acid headgroup (3). The binding of these guests to urea-adamantyl modified poly(propylene imine) dendrimers has been investigated with C-13 NMR and P-31 NMR next to 1D and 2D H-1 NMR techniques. Different amounts of guest 2 have been added to fifth generation dendrimer le, and the observed chemical shift values in C-13 NMR were fitted to a model that assumes 1:1 binding between guest and binding site. An association constant of 400 +/- 95 M-1 is obtained for guest 2 with 41 binding sites per dendrimer. When different amounts of phosphonic acid guest 3 are added to dendrimer le, two different signals are observed in P-31 NMR. Deconvolution gives the fractions of free and bound guest, resulting in an association constant of (4 3) x 104 M-1 and 61 1 binding sites. A statistical analysis shows that guest 2 forms a "polydisperse supramolecular aggregate", while guest 3 is able to form a "monodisperse supramolecular aggregate" when the amount of guest is high enough. The NMR results are compared with dynamic light scattering experiments, and a remarkable agreement is found. Phosphonic acid guest 3 is able to exchange with guest 2, which is in agreement with the obtained association constants, and shows that these techniques can be used to analyze multicomponent dendritic aggregates.

  DOI：

  10.1021/ja052074m