7-(2-hydroxypropanoylamino)-2-(2-ethylhexanoylamino)-1,8-naphthyridine | 1071226-62-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 7-(2-hydroxypropanoylamino)-2-(2-ethylhexanoylamino)-1,8-naphthyridine
• CAS: 1071226-62-4
• 化学式: C₁₉H₂₆N₄O₃
• 分子量: 358.44
• InChiKey: WBCLJSQDAMDPMG-UEWDXFNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  104.21
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-(6-isocyanatohexylaminocarbonylamino)-6-methyl-4-pyrimidinone 、 7-(2-hydroxypropanoylamino)-2-(2-ethylhexanoylamino)-1,8-naphthyridine 在 二月桂酸二丁基锡 作用下， 以 氯仿 为溶剂， 反应 20.0h， 以67%的产率得到
  参考文献：
  名称：

  Influence of Selectivity on the Supramolecular Polymerization of AB-Type Polymers Capable of Both A·A and A·B Interactions

  摘要：

  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.

  DOI：

  10.1021/ja8046409
• 作为产物：
  描述：

  7-(2-(tert-butyldimethylsilyloxy)propanoylamino)-2-(2-ethylhexanoylamino)-1,8-naphthyridine 在 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以86%的产率得到7-(2-hydroxypropanoylamino)-2-(2-ethylhexanoylamino)-1,8-naphthyridine
  参考文献：
  名称：

  Influence of Selectivity on the Supramolecular Polymerization of AB-Type Polymers Capable of Both A·A and A·B Interactions

  摘要：

  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.

  DOI：

  10.1021/ja8046409