4-Decyloxypyridine-2,6-dicarboxylic acid 2-[(6-amino-4-decyloxypyridin-2-yl)amide] 6-[(6-decanoylamino-4-decyloxypyridin-2-yl)amide] | 362620-04-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-Decyloxypyridine-2,6-dicarboxylic acid 2-[(6-amino-4-decyloxypyridin-2-yl)amide] 6-[(6-decanoylamino-4-decyloxypyridin-2-yl)amide]
• CAS: 362620-04-0
• 化学式: C₅₇H₉₃N₇O₆
• 分子量: 972.409
• InChiKey: HTKVYRNSCKDYNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.6
• 重原子数：
  70.0
• 可旋转键数：
  43.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  179.68
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  4-Decyloxypyridine-2,6-dicarboxylic acid 2-[(6-amino-4-decyloxypyridin-2-yl)amide] 6-[(6-decanoylamino-4-decyloxypyridin-2-yl)amide] 、 4-Decyloxypyridine-2,6-dicarboxylic acid dichloride 以 甲苯 为溶剂， 反应 12.0h， 以43 mg的产率得到4-Decyloxypyridine-2,6-dicarboxylic acid bis(6-{[6-(6-decanoylamino-4-decyloxypyridin-2-ylcarbamoyl)-4-decyloxypyridine-2-carbonyl]amino}-4-decyloxypyridin-2-ylcarbamoyl)amide
  参考文献：
  名称：

  Helical Molecular Programming: Supramolecular Double Helices by Dimerization of Helical Oligopyridine-dicarboxamide Strands

  摘要：

  Helically preorganized oligopyridine-dicarboxamide strands are found to undergo dimerization into double helical supramolecular architectures. Dimerization of single helical strands with five or seven pyridine rings has been characterized by NMR and mass spectrometry in various solvent/ temperature conditions. Solution studies and stochastic dynamic simulations consistently show an increasing duplex stability with increasing strand length. The double helical structures of three different dimers was characterized in the solid phase by X-ray diffraction analysis. Both aromatic stacking and hydrogen bonding contribute the double helical arrangement of the oligopyridine-dicarboxamide strand. Inter-strand interactions involve extensive face-to-face overlap between aromatic rings, which is not possible in the single helical monomers. Most hydrogen bonds occur within each strand of the duplex and stabilize its helical shape. Some inter-strand hydrogen bonds are found in the crystal structures. Dynamic studies by NMR as well as by molecular modeling computations yield structural and kinetic information on the double helices and on monomer-dimer interconversion. In addition, they reveal the presence of a spring-like extension/compression as well as rotational displacement motions.

  DOI：

  10.1002/1521-3765(20010702)7:13<2810::aid-chem2810>3.0.co;2-5
• 作为产物：
  描述：

  在 氢氧化钾 、 正丁基锂 、 溴 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 甲苯 为溶剂， 反应 42.5h， 生成 4-Decyloxypyridine-2,6-dicarboxylic acid 2-[(6-amino-4-decyloxypyridin-2-yl)amide] 6-[(6-decanoylamino-4-decyloxypyridin-2-yl)amide]
  参考文献：
  名称：

  Helical Molecular Programming: Supramolecular Double Helices by Dimerization of Helical Oligopyridine-dicarboxamide Strands

  摘要：

  Helically preorganized oligopyridine-dicarboxamide strands are found to undergo dimerization into double helical supramolecular architectures. Dimerization of single helical strands with five or seven pyridine rings has been characterized by NMR and mass spectrometry in various solvent/ temperature conditions. Solution studies and stochastic dynamic simulations consistently show an increasing duplex stability with increasing strand length. The double helical structures of three different dimers was characterized in the solid phase by X-ray diffraction analysis. Both aromatic stacking and hydrogen bonding contribute the double helical arrangement of the oligopyridine-dicarboxamide strand. Inter-strand interactions involve extensive face-to-face overlap between aromatic rings, which is not possible in the single helical monomers. Most hydrogen bonds occur within each strand of the duplex and stabilize its helical shape. Some inter-strand hydrogen bonds are found in the crystal structures. Dynamic studies by NMR as well as by molecular modeling computations yield structural and kinetic information on the double helices and on monomer-dimer interconversion. In addition, they reveal the presence of a spring-like extension/compression as well as rotational displacement motions.

  DOI：

  10.1002/1521-3765(20010702)7:13<2810::aid-chem2810>3.0.co;2-5