N-(6-isocyanatohexyl)-N'-(6-ethyl-4-oxo-1,4-dihydropyrimidin-2-yl)urea | 1261138-69-5

• 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: N-(6-isocyanatohexyl)-N'-(6-ethyl-4-oxo-1,4-dihydropyrimidin-2-yl)urea
• CAS: 1261138-69-5
• 化学式: C₁₄H₂₁N₅O₃
• 分子量: 307.352
• InChiKey: UFXWABCCFOYRAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.35
• 重原子数：
  22.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  116.31
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-氨基-4-羟基-6-乙基嘧啶 、 1,6-己二异氰酸酯 反应 2.0h， 以70%的产率得到N-(6-isocyanatohexyl)-N'-(6-ethyl-4-oxo-1,4-dihydropyrimidin-2-yl)urea
  参考文献：
  名称：

  Variable Microwave Effects in the Synthesis of Ureidopyrimidinones: the Role of Heterogeneity

  摘要：

  Microwave-irradiated and conventionally heated nucleophilic additions of various C-6 substituted isocytosines (methyl, ethyl, isopropyl, and phenyl) to (di)isocyanates have been compared. As compared to conventional heating, the heterogeneous reaction mixtures showed higher reaction rates on using microwave heating. Variation of C-6 substituent, temperature, and amount of cosolvent influenced significantly the magnitude of these microwave effects. The magnitude of the microwave effect was governed by the solubility and the intrinsic reactivity of the variation in C-6 substitution on isocytosine. Presumably, the liquid layer near the solid surface is the area where selective heating by microwaves is occurring. As a consequence of locally higher temperatures, the solubility of the reactant as well as the rate coefficient of the reaction increase. Thus, higher reaction rates are observed than those corresponding with the measured bulk temperature. The observed microwave effects have a thermal rationale based on direct, fast, and selective heating, and the local heating effect is not found during conventional heating. This finding is crucial for a justified process scale-up scenario.

  DOI：

  10.1021/op100202j