2-amino-6-(dibutylamino) 4-pyrimidinol | 1016639-44-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-amino-6-(dibutylamino) 4-pyrimidinol
• 英文别名: 2-amino-4-(dibutylamino)-1H-pyrimidin-6-one
• CAS: 1016639-44-3
• 化学式: C₁₂H₂₂N₄O
• 分子量: 238.333
• InChiKey: QGVBTEDWRCUCPD-UHFFFAOYSA-N

物化性质

• 熔点：
  161 °C
• 沸点：
  360.6±45.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-6-(dibutylamino) 4-pyrimidinol 、 1,6-己二异氰酸酯 反应 1.0h， 以50%的产率得到1-(4-(dibutylamino)-6-hydroxypyrimidin-2-yl)-3-(6-isocyanatohexyl)urea
  参考文献：
  名称：

  Alternation and tunable composition in hydrogen bonded supramolecular copolymers

  摘要：

  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。

  DOI：

  10.1039/c3cc46611f
• 作为产物：
  描述：

  二正丁胺 、 2-氨基-6-氯-4-羟基嘧啶 反应 5.0h， 以64%的产率得到2-amino-6-(dibutylamino) 4-pyrimidinol
  参考文献：
  名称：

  使用氢键基序的超分子自排序网络

  摘要：

  超分子化学当前的一个目标是模拟复杂的自排序系统之间的转变，这些系统代表了自然界调节功能的标志。在这项工作中，创建了一个包含线性氢基序的自排序网络。选择六个能够进行高保真和混杂分子识别的氢键基序产生了一个复杂的自分类系统，其中包括能够自恋和社会自分类的基序。通过实验和计算检查各个组件之间的相互作用，为级联每个阶段的产物分布提供了基本原理。这一推理通过六个构建块的最多五次连续添加而成立，从而构建了一个仿生网络，其中不同组件的存在或不存在提供了多种独特的途径来实现不同的自排序配置。

  DOI：

  10.1002/chem.201804791

文献信息

• Direct Detection of Hydrogen Bonds in Supramolecular Systems Using ¹H–¹⁵N Heteronuclear Multiple Quantum Coherence Spectroscopy
  作者：Michael A. Jinks、Mark Howard、Federica Rizzi、Stephen M. Goldup、Andrew D. Burnett、Andrew J. Wilson

  DOI：10.1021/jacs.2c10742

  日期：2022.12.21

  Hydrogen-bonded supramolecular systems are usually characterized in solution through analysis of NMR data such as complexation-induced shifts and nuclear Overhauser effects (nOe). Routine direct detection of hydrogen bonding particularly in multicomponent mixtures, even with the aid of 2D NMR experiments for full assignment, is more challenging. We describe an elementary rapid 1H–15N HMQC NMR experiment which addresses

  氢键超分子系统通常通过分析 NMR 数据（例如络合引起的位移和核 Overhauser 效应 (nOe)）在溶液中表征。氢键的常规直接检测，尤其是在多组分混合物中，即使借助 2D NMR 实验进行完整分配，也更具挑战性。我们描述了一个基本的快速1 H– 15 N HMQC NMR 实验，该实验无需复杂的脉冲序列即可应对这些挑战。在易于获得的条件下（243/263 K，50 mM 溶液）和天然15 N 丰度，15的明确分配N 共振有助于直接检测机械互锁结构中的分子内和分子间氢键以及四重氢键二聚体─二烷基氨基脲基嘧啶酮、脲基嘧啶酮和二氨基萘啶酮─在单组分或多组分混合物中建立互变异构构型、构象，并解析自分类物种形成。
• 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.
• Supramolecular Buffering by Ring–Chain Competition
  作者：Tim F. E. Paffen、Gianfranco Ercolani、Tom F. A. de Greef、E. W. Meijer

  DOI：10.1021/ja5110377

  日期：2015.2.4

  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.