4-Decyloxypyridine-2,6-dicarboxylic acid bis[(6-amino-4-decyloxypyridin-2-yl)amide] | 362620-03-9

• 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 bis[(6-amino-4-decyloxypyridin-2-yl)amide]
• 英文别名: 2-N,6-N-bis(6-amino-4-decoxypyridin-2-yl)-4-decoxypyridine-2,6-dicarboxamide
• CAS: 362620-03-9
• 化学式: C₄₇H₇₅N₇O₅
• 分子量: 818.156
• InChiKey: ABKDNWDLRDVUBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.4
• 重原子数：
  59
• 可旋转键数：
  34
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  177
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  癸酰氯 、 4-Decyloxypyridine-2,6-dicarboxylic acid bis[(6-amino-4-decyloxypyridin-2-yl)amide] 在 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 13.0h， 以60 mg的产率得到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
• 作为产物：
  描述：

  dimethyl 4-decyloxy-2,6-pyridinedicarboxylate 在 氢氧化钾 、 正丁基锂 、 氨 、 溴 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 正己烷 为溶剂， 反应 41.5h， 生成 4-Decyloxypyridine-2,6-dicarboxylic acid bis[(6-amino-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

文献信息

• Double versus single helical structures of oligopyridine-dicarboxamide strands. Part 1: Effect of oligomer length
  作者：Hua Jiang、Victor Maurizot、Ivan Huc

  DOI：10.1016/j.tet.2004.07.078

  日期：2004.10

  strands. NMR studies show that both double helices and single helices become more stable when strand length increases. The measured values of enthalpy and entropy of hybridization for oligomers of various length show that the enthalpic gain constantly decreases with strand length. This can be interpreted as being the result of an increasing enthalpic price of the spring-like extension that the strand undergoes

  先前显示2，6-二氨基吡啶和2，6-吡啶二甲酸的低聚酰胺折叠成单螺旋单体并杂交成双螺旋二聚体。使用新的收敛方案合成了一系列新的包含5至15个吡啶单元，4-癸氧基残基和氨基甲酸苄酯端基的低聚物，该方案涉及二胺和二酸的早期不对称化。这些化合物杂交成双螺旋的方法为1在各种温度下于氯仿溶液中的1 H NMR光谱。出乎意料的是，这些研究表明，二聚化随着寡聚体长度的增加而增加，直到某个点，然后降低到最长链的不可检测水平。NMR研究表明，当链长增加时，双螺旋和单螺旋都变得更稳定。各种长度的寡聚物的焓和杂交熵的测量值表明，焓增益随着链长的增加而不断减小。这可以解释为由于链长随着杂交而经历的弹簧状延伸的焓价增加的结果。另一方面，杂交的熵损失也随着链长的增加而不断减少。想必，单体的螺旋预组织随着链长度的增加而增加，这允许较长的链以最小的运动自由度杂交，即以较低的熵价杂交。这两个因素之间的竞争导致具有中等长度的链的杂交达到最大。