1-(4-(dibutylamino)-6-hydroxypyrimidin-2-yl)-3-(6-isocyanatohexyl)urea | 1071226-65-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(4-(dibutylamino)-6-hydroxypyrimidin-2-yl)-3-(6-isocyanatohexyl)urea
• 英文别名: 2-(6-isocyanatohexylaminocarbonylamino)-6-(dibutylamino) 4-pyrimidinol
• CAS: 1071226-65-7
• 化学式: C₂₀H₃₄N₆O₃
• 分子量: 406.528
• InChiKey: ORTPLCNGDSXWNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  29.0
• 可旋转键数：
  15.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  119.81
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1,12-十二烷二醇 、 1-(4-(dibutylamino)-6-hydroxypyrimidin-2-yl)-3-(6-isocyanatohexyl)urea 在 二月桂酸二丁基锡 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以19.7%的产率得到dodecane-1,12-diyl bis((6-(3-(4-(dibutylamino)-6-hydroxypyrimidin-2-yl)ureido)hexyl)carbamate)
  参考文献：
  名称：

  Supramolecular Buffering by Ring–Chain Competition

  摘要：

  Recently, we reported an organocatalytic system in which buffering of the molecular catalyst by supramolecular interactions results in a robust system displaying concentration-independent catalytic activity. Here, we demonstrate the design principles of the supramolecular buffering by ring-chain competition using a combined experimental and theoretical approach. Our analysis shows that supramolecular buffering of a molecule is caused by its participation as a chain stopper in supramolecular ring-chain equilibria, and we reveal here the influence of various thermodynamic parameters. Model predictions based on independently measured equilibrium constants corroborate experimental data of several molecular systems in which buffering occurs via competition between cyclization, growth of linear chains, and end-capping by the chain-stopper. Our analysis reveals that the effective molarity is the critical parameter in optimizing the broadness of the concentration regime in which supramolecular ring-chain buffering occurs as well as the maximum concentration of the buffered molecule. To conclude, a side-by-side comparison of supramolecular ring-chain buffering, pH buffering, and molecular titration is presented.

  DOI：

  10.1021/ja5110377
• 作为产物：
  描述：

  二正丁胺 以 乙二醇 为溶剂， 反应 19.0h， 生成 1-(4-(dibutylamino)-6-hydroxypyrimidin-2-yl)-3-(6-isocyanatohexyl)urea
  参考文献：
  名称：

  Supramolecular Buffering by Ring–Chain Competition

  摘要：

  Recently, we reported an organocatalytic system in which buffering of the molecular catalyst by supramolecular interactions results in a robust system displaying concentration-independent catalytic activity. Here, we demonstrate the design principles of the supramolecular buffering by ring-chain competition using a combined experimental and theoretical approach. Our analysis shows that supramolecular buffering of a molecule is caused by its participation as a chain stopper in supramolecular ring-chain equilibria, and we reveal here the influence of various thermodynamic parameters. Model predictions based on independently measured equilibrium constants corroborate experimental data of several molecular systems in which buffering occurs via competition between cyclization, growth of linear chains, and end-capping by the chain-stopper. Our analysis reveals that the effective molarity is the critical parameter in optimizing the broadness of the concentration regime in which supramolecular ring-chain buffering occurs as well as the maximum concentration of the buffered molecule. To conclude, a side-by-side comparison of supramolecular ring-chain buffering, pH buffering, and molecular titration is presented.

  DOI：

  10.1021/ja5110377

文献信息

• Alternation and tunable composition in hydrogen bonded supramolecular copolymers
  作者：Thorsten Felder、Tom F. A. de Greef、Marko M. L. Nieuwenhuizen、Rint P. Sijbesma

  DOI：10.1039/c3cc46611f

  日期：——

  A quadruple hydrogen bonded supramolecular copolymer is reported which combines preferred alternation with a continuously tunable composition.

  报道了一种四重氢键超分子共聚物，它将首选交替结构与连续可调的组成相结合。
• Influence of Selectivity on the Supramolecular Polymerization of AB-Type Polymers Capable of Both A·A and A·B Interactions
  作者：Tom F. A. de Greef、Gianfranco Ercolani、G. B. W. L. Ligthart、E. W. Meijer、Rint P. Sijbesma

  DOI：10.1021/ja8046409

  日期：2008.10.15

  The supramolecular polymerization of two AB-type monomers capable of hydrogen-bond-mediated A.B heterocoupling and A.A homocoupling is discussed. The AB-type supramolecular polymerization is based on the strong interaction between self-dimerizing 2-ureido-pyrimidinone (UPy) and 2,7-diamido-1,8-naphthyridine (NaPy). In an effort to reduce the "self-stoppered" effect that is inherently present in these supramolecular polymerizations we used a novel ureido-pyrimidinone substituted with a dibutylamino group at the pyrimidinone ring. As a result of the substitution, the dimerization constant of the novel UPy unit is lowered compared to the previous UPy unit while the heterodimerization strength is retained. Unexpectedly, the increased selectivity toward heteroassociation not only influences the concentration-dependent degree of polymerization due to reduction of the "self-stoppered" effect but also has a pronounced effect on the ring-chain equilibrium by increasing the tendency to cyclize. In order to quantitatively explain our results, a model was developed that accurately predicts the degree of polymerization by taking into account homo- and heterodimerization as well as cyclization. Finally, molecular weight distributions for noncyclizing AB supramolecular polymerizations with and without a reversible A-A interaction are calculated. It is found that the molecular weight distribution becomes narrower when A-A interactions are present.