1,3-diethyl-5-(4-nitrobenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione | 1356399-52-4

• 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: 1,3-diethyl-5-(4-nitrobenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
• CAS: 1356399-52-4
• 化学式: C₁₅H₁₅N₃O₅
• 分子量: 317.301
• InChiKey: FWFZRJCGMSXQJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  100.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1,3-二乙基嘧啶-2,4,6(1H,3H,5H)-三酮 、 1,3-diethyl-5-(4-nitrobenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione 在 溴 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以92%的产率得到1,1′,3,3′-tetraethyl-5-(4-nitrophenyl)-1,5-dihydro-2H,2′H-spiro[furo[2,3-d]pyrimidine-6,5′-pyrimidine]-2,2′,4,4′,6′(1′H,3H,3′H)-pentaone
  参考文献：
  名称：

  Electrocatalytic and chemical assembling of N,N′-dialkylbarbituric acids and aldehydes: efficient cascade approach to the spiro-[furo[2,3-d]pyrimidine-6,5′-pyrimidine]-2,2′,4,4′,6′-(1′H,3H,3′H)-pentone framework

  摘要：

  Electrocatalytic assembling of aldehydes and N,N'-dialkylbarbituric acids leads to selective and efficient formation of substituted 1,5-dihydro-2H,2'H-spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine]-2,2',4,4',6'-(1'H,3H,3'H)-pentones in 70-85% yields as a result of the complex cascade process. The electrocatalytic process smoothly proceeds with aromatic aldehydes bearing both electron-donating and electron-withdrawing groups, and allows for the selective and efficient one-step formation of spirobarbiturates containing furo[2,3-d]pyrimidine scaffold, which are a perspective class of compounds with prominent pharmacological and physiological activity. The application of the effective electrocatalytic cascade method to the formation of medicinally relevant spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine]-2,2',4,4',6'-(1'H,3H,3'H)-pentones is also beneficial from the viewpoint of diversity-oriented large-scale processes and represents a novel, facile and environmentally benign synthetic concept for electrocatalytic cascade reaction strategy. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.057