(1R,3S)-N1,N3-bis(6-((tributyl-l5-phosphaneylidene)amino)pyridazin-3-yl)cyclopentane-1,3-diamine | 847946-53-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (1R,3S)-N1,N3-bis(6-((tributyl-l5-phosphaneylidene)amino)pyridazin-3-yl)cyclopentane-1,3-diamine
• CAS: 847946-53-6
• 化学式: C₃₇H₆₈N₈P₂
• 分子量: 686.948
• InChiKey: CFPAAQHPKYMPNS-CZFRINIUSA-N

物化性质

• 熔点：
  218-222 °C
• 沸点：
  833.6±75.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.18
• 重原子数：
  47.0
• 可旋转键数：
  24.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  100.34
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3,4,5-tri(n-butyloxy)benzoic acid 、 (1R,3S)-N1,N3-bis(6-((tributyl-l5-phosphaneylidene)amino)pyridazin-3-yl)cyclopentane-1,3-diamine 以 甲苯 为溶剂， 反应 24.0h， 以27%的产率得到3,4,5-tributoxy-N-[6-[[(1S,3R)-3-[[6-[(3,4,5-tributoxybenzoyl)amino]pyridazin-3-yl]amino]cyclopentyl]amino]pyridazin-3-yl]benzamide
  参考文献：
  名称：

  Duplex Molecular Strands Based on the 3,6-Diaminopyridazine Hydrogen Bonding Motif:  Amplifying Small-Molecule Self-Assembly Preferences through Preorganization and Iterative Arrangement of Binding Residues

  摘要：

  Structural parameters obtained through single-crystal X-ray diffraction analysis of the one-dimensional H-bonding motif expressed by 3,6-diaminopyridazine are applied to the design of related monomeric, dimeric, and trimeric duplex molecular strands. The mode of assembly and the interstrand affinity of the oligomers are established in solution by H-1 NMR dilution experiments, isothermal titration calorimetry (ITC), and vapor pressure osmometry. Single-crystal X-ray crystallographic analysis of the dimeric diaminopyriclazine 2a corroborates the intended duplex mode of assembly. Binding free energy per unimer (-DeltaGdegrees/n) increases upon extension from monomer to dimer to trimer, signifying a positive cooperative effect. Micromolar binding affinity (K-d = 1.25 +/- 0.1 muM) was determined for the duplex trimer by ITC in 1,2-dichloroethane at 20degreesC. These data provide further insight into the structural and interactional features of synthetic duplex oligomers required for high-affinity, high-specificity binding and define new recognition elements for use in nanoscale assembly.

  DOI：

  10.1021/ja044566p
• 作为产物：
  描述：

  cis-1,3-cyclopentyldiamine dihydrochloride 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 9.0h， 生成 (1R,3S)-N1,N3-bis(6-((tributyl-l5-phosphaneylidene)amino)pyridazin-3-yl)cyclopentane-1,3-diamine
  参考文献：
  名称：

  Duplex Molecular Strands Based on the 3,6-Diaminopyridazine Hydrogen Bonding Motif:  Amplifying Small-Molecule Self-Assembly Preferences through Preorganization and Iterative Arrangement of Binding Residues

  摘要：

  Structural parameters obtained through single-crystal X-ray diffraction analysis of the one-dimensional H-bonding motif expressed by 3,6-diaminopyridazine are applied to the design of related monomeric, dimeric, and trimeric duplex molecular strands. The mode of assembly and the interstrand affinity of the oligomers are established in solution by H-1 NMR dilution experiments, isothermal titration calorimetry (ITC), and vapor pressure osmometry. Single-crystal X-ray crystallographic analysis of the dimeric diaminopyriclazine 2a corroborates the intended duplex mode of assembly. Binding free energy per unimer (-DeltaGdegrees/n) increases upon extension from monomer to dimer to trimer, signifying a positive cooperative effect. Micromolar binding affinity (K-d = 1.25 +/- 0.1 muM) was determined for the duplex trimer by ITC in 1,2-dichloroethane at 20degreesC. These data provide further insight into the structural and interactional features of synthetic duplex oligomers required for high-affinity, high-specificity binding and define new recognition elements for use in nanoscale assembly.

  DOI：

  10.1021/ja044566p