1-propyl-5-cyclopropyluracil

• 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: 1-propyl-5-cyclopropyluracil
• 英文别名: 5-Cyclopropyl-1-propylpyrimidine-2,4-dione
• 化学式: C₁₀H₁₄N₂O₂
• 分子量: 194.233
• InChiKey: TZRDPLISURBYIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  环丙乙酸 在 吡啶 、 正丁基锂 、 草酰氯 、 N-环己基异丙基胺 、 N,N-二甲基甲酰胺 、 氯乙酸 作用下， 以 水 、 苯 为溶剂， 反应 22.75h， 生成 1-propyl-5-cyclopropyluracil
  参考文献：
  名称：

  Free Radical Rearrangements in Uracil Derivatives

  摘要：

  As part of an effort to develop general probes for radical reactions involving DNA bases, several uracil derivatives were synthesized. The rates of the cyclopropyl carbinyl rearrangement in these systems were evaluated by means of competition experiments. The results indicate that when a cyclopropyl group is substituted in the 5-position of uracil, the rearrangement occurs very slowly-with a rate constant of <2.5 x 10(4) s(-1). On the other hand, the analog of the 5-hexenyl radical cyclization onto the 5,6-double bond of uracil derivatives occurs with rates which were similar to the parent process: (4.0-8.9) x 10(4) s(-1). The experimental results along with semiempirical calculations show that radicals 23 and 25 are unusually stable species. These results explain why no rearrangements are observed when a cyclopropyl-substituted thymine dimer is cleaved by reductive single electron transfer.

  DOI：

  10.1021/jo00096a021

文献信息

• Free Radical Rearrangements in Uracil Derivatives
  作者：David J. Fenick、Daniel E. Falvey

  DOI：10.1021/jo00096a021

  日期：1994.8

  As part of an effort to develop general probes for radical reactions involving DNA bases, several uracil derivatives were synthesized. The rates of the cyclopropyl carbinyl rearrangement in these systems were evaluated by means of competition experiments. The results indicate that when a cyclopropyl group is substituted in the 5-position of uracil, the rearrangement occurs very slowly-with a rate constant of <2.5 x 10(4) s(-1). On the other hand, the analog of the 5-hexenyl radical cyclization onto the 5,6-double bond of uracil derivatives occurs with rates which were similar to the parent process: (4.0-8.9) x 10(4) s(-1). The experimental results along with semiempirical calculations show that radicals 23 and 25 are unusually stable species. These results explain why no rearrangements are observed when a cyclopropyl-substituted thymine dimer is cleaved by reductive single electron transfer.