2-(6-hydroxyhexylureido)-6-tridecyl-4[1H]-pyrimidinone | 288569-71-1

• 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: 2-(6-hydroxyhexylureido)-6-tridecyl-4[1H]-pyrimidinone
• CAS: 288569-71-1
• 化学式: C₂₄H₄₄N₄O₃
• 分子量: 436.638
• InChiKey: DQCYEXUMMSOHLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  31.0
• 可旋转键数：
  19.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  107.11
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-芘丁酸 、 2-(6-hydroxyhexylureido)-6-tridecyl-4[1H]-pyrimidinone 在 4-二甲氨基吡啶 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 以49%的产率得到2-((4-(1-pyrenyl)-1-oxo-butyloxy)hexylureido)-6-tridecyl-4[1H]pyrimidinone
  参考文献：
  名称：

  Stability and Lifetime of Quadruply Hydrogen Bonded 2-Ureido-4[1H]-pyrimidinone Dimers

  摘要：

  2-Ureido-4[1H]-pyrimidinones are known to dimerize via a strong quadruple hydrogen bond array. A. detailed study of the dimerization constant and lifetime of the dimer is presented here. Excimer fluorescence of pyrene-labeled 2-ureido-4[1H]-pyrimidinone Ib was used to determine a dimerization constant K-dim, of 6 x 10(7) M-1 in CHCl3, 1 x 10(7) M-1 in chloroformsaturated with water, and 6 x 10(8) M-1 in toluene (all at 298 K). Under these conditions, the preexchange lifetime of the similar dimers of both 1d and 1e is 170 ms in CDCl3, 80 ms in wet CDCl3, and 1.7 s in toluene-dp, as determined by dynamic NMR spectroscopy Association rate constants were calculated from the Kdim values and the preexchange lifetimes. The resulting values are significantly lower than the diffusion-controlled association rate constants calculated using the Stokes-Einstein and the Debeije equations. This difference is ascribed to a tautomeric equilibrium of the monomer between the dimerizing 4[1K]-pyrimidinone and nondimerizing 6[1H]-pyrimidinone tautomers, which is unfavorable for dimerization.

  DOI：

  10.1021/ja000435m
• 作为产物：
  描述：

  6-氨基-1-己醇 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2-(6-hydroxyhexylureido)-6-tridecyl-4[1H]-pyrimidinone
  参考文献：
  名称：

  Stability and Lifetime of Quadruply Hydrogen Bonded 2-Ureido-4[1H]-pyrimidinone Dimers

  摘要：

  2-Ureido-4[1H]-pyrimidinones are known to dimerize via a strong quadruple hydrogen bond array. A. detailed study of the dimerization constant and lifetime of the dimer is presented here. Excimer fluorescence of pyrene-labeled 2-ureido-4[1H]-pyrimidinone Ib was used to determine a dimerization constant K-dim, of 6 x 10(7) M-1 in CHCl3, 1 x 10(7) M-1 in chloroformsaturated with water, and 6 x 10(8) M-1 in toluene (all at 298 K). Under these conditions, the preexchange lifetime of the similar dimers of both 1d and 1e is 170 ms in CDCl3, 80 ms in wet CDCl3, and 1.7 s in toluene-dp, as determined by dynamic NMR spectroscopy Association rate constants were calculated from the Kdim values and the preexchange lifetimes. The resulting values are significantly lower than the diffusion-controlled association rate constants calculated using the Stokes-Einstein and the Debeije equations. This difference is ascribed to a tautomeric equilibrium of the monomer between the dimerizing 4[1K]-pyrimidinone and nondimerizing 6[1H]-pyrimidinone tautomers, which is unfavorable for dimerization.

  DOI：

  10.1021/ja000435m