5-(cyclohexylmethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione | 144459-85-8

• 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: 5-(cyclohexylmethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione
• 英文别名: 5-cyclohexylmethyl-1,3-dimethyluracil；5-(Cyclohexylmethyl)-1,3-dimethylpyrimidine-2,4-dione
• CAS: 144459-85-8
• 化学式: C₁₃H₂₀N₂O₂
• 分子量: 236.314
• InChiKey: AKZWGOJIOXCECW-UHFFFAOYSA-N

物化性质

• 沸点：
  340.6±25.0 °C(Predicted)
• 密度：
  1.109±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-(cyclohexylmethyl)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione 在 samarium diiodide 、 水 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 2.02h， 以77%的产率得到5-(cyclohexylmethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Switching between Reaction Pathways by an Alcohol Cosolvent Effect: SmI₂–Ethylene Glycol vs SmI₂–H₂O Mediated Synthesis of Uracils

  摘要：

  A chemoselective switch between reaction pathways by an alcohol cosolvent effect in a general SmI2-mediated synthesis of uracil derivatives is described. The method relies on the use of coordinating solvents to increase the redox potential of Sm(II) and results in a chemoselective 1,2-reduction (SmI2H2O) or 1,2-migration via in situ generated N-acyliminium ions (SmI(2)ethylene glycol, EG). This work exploits the mild conditions of the SmI2-mediated monoreduction of barbituric acids and offers an attractive protocol for the synthesis of uracil derivatives with biological activity from readily accessible building blocks.

  DOI：

  10.1021/ol502775w

文献信息

• Free Radical Alkylation of 1,3-Dimethyluracils and Caffeine with Benzoyl Peroxide
  作者：Toshio Itahara、Naoko Ide

  DOI：10.1246/bcsj.65.2045

  日期：1992.8

  3-dimethyluracils, although a steric effect of the methyl group at 6-position complicated the reaction. On the other hand, a similar treatment of 1,3-dimethylthymine led to alkylation of the methyl group at 5-position. The reaction of caffeine gave 8-alkylcaffeines and alkyl acetates were used as favorable solvents with respect to synthesis of 8-alkylcaffeines.

  1,3-二甲基尿嘧啶和 1,3,6-三甲基尿嘧啶与过氧化苯甲酰在环己烷、乙酸乙酯和乙腈中反应得到相应的 5-烷基-1,3-二甲基尿嘧啶，尽管甲基在 6-位置使反应复杂化。另一方面，1,3-二甲基胸腺嘧啶的类似处理导致5-位甲基的烷基化。咖啡因反应得到 8-烷基咖啡因，乙酸烷基酯用作合成 8-烷基咖啡因的有利溶剂。
• Switching between Reaction Pathways by an Alcohol Cosolvent Effect: SmI₂–Ethylene Glycol vs SmI₂–H₂O Mediated Synthesis of Uracils
  作者：Michal Szostak、Malcolm Spain、Brice Sautier、David J. Procter

  DOI：10.1021/ol502775w

  日期：2014.11.7

  A chemoselective switch between reaction pathways by an alcohol cosolvent effect in a general SmI2-mediated synthesis of uracil derivatives is described. The method relies on the use of coordinating solvents to increase the redox potential of Sm(II) and results in a chemoselective 1,2-reduction (SmI2H2O) or 1,2-migration via in situ generated N-acyliminium ions (SmI(2)ethylene glycol, EG). This work exploits the mild conditions of the SmI2-mediated monoreduction of barbituric acids and offers an attractive protocol for the synthesis of uracil derivatives with biological activity from readily accessible building blocks.