N-<3-(9-adeninyl)propyl>-4,13-diaza-18-crown-6 | 156488-53-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: N-<3-(9-adeninyl)propyl>-4,13-diaza-18-crown-6
• CAS: 156488-53-8
• 化学式: C₂₀H₃₅N₇O₄
• 分子量: 437.542
• InChiKey: XOMSGYGYAUUUCP-UHFFFAOYSA-N

物化性质

• 沸点：
  669.5±65.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.23
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  121.81
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  1-(3-溴丙基)胸腺嘧啶 、 N-<3-(9-adeninyl)propyl>-4,13-diaza-18-crown-6 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以55%的产率得到N-<3-(1-thyminyl)propyl>-N'-<3-(9-adeninyl)propyl>-4,13-diaza-18-crown-6
  参考文献：
  名称：

  Molecular Boxes Derived from Crown Ethers and Nucleotide Bases: Probes for Hoogsteen vs Watson-Crick H-Bonding and Other Base-Base Interactions in Self-Assembly Processes

  摘要：

  Bibracchial lariat ethers based upon 4, 13-diaza-18-crown-6 having -(CH2)(3)-sidearms terminated in adenine or thymine have been prepared and characterized. The three structures are as follows: adenine-(CH2)(3)-(N18N)(CH2)(3)-adenine (A-O-A), thymine-(CH2)(3)-(N18N)-(CH2)(3)-thymine (T-O-T), and adenine-(CH2)(3)-(N18N)-(CH2)(3)-thymine (A-O-T). Association of the nucleotide bases was expected to afford molecular boxes or other aggregates that would be stabilized by interactions between or among the nucleotide bases. These compounds have been studied in solution by H-1-NMR spectroscopy and by vapor pressure osmometry to determine the extent of association as well as what interactions occur between the bases. The H-1-NMR solution studies involved both temperature and concentration dependence and NOE studies. Several lines of evidence make clear that association does occur in CDCl3 with an association constant for A-O-A with T-O-T of 855 M(-1). Both intra- and intermolecular H-bonding interactions are detected. Hoogsteen binding modes appear to play a very important role in these flexible systems. The A-O-A.T-O-T box may also comprise a ditopic receptor system in which the sides of the box are Ade::Thy pairs and the ends are crown ethers. We have studied such systems in the presence of decanediyldiammonium and dodecanediyldiammonium salts and report evidence for a ternary induced-fit receptor complex.

  DOI：

  10.1021/ja00093a005
• 作为产物：
  描述：

  腺嘌呤 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 N-<3-(9-adeninyl)propyl>-4,13-diaza-18-crown-6
  参考文献：
  名称：

  Molecular Boxes Derived from Crown Ethers and Nucleotide Bases: Probes for Hoogsteen vs Watson-Crick H-Bonding and Other Base-Base Interactions in Self-Assembly Processes

  摘要：

  Bibracchial lariat ethers based upon 4, 13-diaza-18-crown-6 having -(CH2)(3)-sidearms terminated in adenine or thymine have been prepared and characterized. The three structures are as follows: adenine-(CH2)(3)-(N18N)(CH2)(3)-adenine (A-O-A), thymine-(CH2)(3)-(N18N)-(CH2)(3)-thymine (T-O-T), and adenine-(CH2)(3)-(N18N)-(CH2)(3)-thymine (A-O-T). Association of the nucleotide bases was expected to afford molecular boxes or other aggregates that would be stabilized by interactions between or among the nucleotide bases. These compounds have been studied in solution by H-1-NMR spectroscopy and by vapor pressure osmometry to determine the extent of association as well as what interactions occur between the bases. The H-1-NMR solution studies involved both temperature and concentration dependence and NOE studies. Several lines of evidence make clear that association does occur in CDCl3 with an association constant for A-O-A with T-O-T of 855 M(-1). Both intra- and intermolecular H-bonding interactions are detected. Hoogsteen binding modes appear to play a very important role in these flexible systems. The A-O-A.T-O-T box may also comprise a ditopic receptor system in which the sides of the box are Ade::Thy pairs and the ends are crown ethers. We have studied such systems in the presence of decanediyldiammonium and dodecanediyldiammonium salts and report evidence for a ternary induced-fit receptor complex.

  DOI：

  10.1021/ja00093a005