1,3-dimethyl-7,8,9,9a-tetrahydrobenzofuro[3,2-d]pyrimidine-2,4-dione | 370877-15-9

• 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-dimethyl-7,8,9,9a-tetrahydrobenzofuro[3,2-d]pyrimidine-2,4-dione
• 英文别名: 1,3-Dimethyl-7,8,9,9a-tetrahydro-[1]benzofuro[3,2-d]pyrimidine-2,4-dione；1,3-dimethyl-7,8,9,9a-tetrahydro-[1]benzofuro[3,2-d]pyrimidine-2,4-dione
• CAS: 370877-15-9
• 化学式: C₁₂H₁₄N₂O₃
• 分子量: 234.255
• InChiKey: KOPGCBSQTQIYQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-dimethyl-7,8,9,9a-tetrahydrobenzofuro[3,2-d]pyrimidine-2,4-dione 在 palladium on activated charcoal 作用下， 以 二苯醚 为溶剂， 反应 0.5h， 以40%的产率得到1,3-dimethylbenzofuro[3,2-d]pyrimidine-2,4-dione
  参考文献：
  名称：

  Regioselective synthesis of pyrimidine annelated heterocycles from 6-(cyclohex-2-enyl)-1,3-dimethyl-5-hydroxyuracil

  摘要：

  6-(Cyclohex-2-enyl)-1,3-dimethyl-5-hydroxyuracil when treated with bromine in chloroform at 0-5 degreesC for 6 h furnishes 6-bromo-1,3-dimethylhexahydrobenzofuro[3,2-d]pyrimidine-2,4-dione in 80% yield. The same heterocycle is also obtained in 90% yield on treatment of the same substrate with pyridine hydrobromide perbromide for 30 min or with hexamethylenetetramine hydrotribromide for 15 min in methylene chloride at 0-5 degreesC. Cyclization of the same substrate with bis-benzonitrile palladium(II) chloride in benzene in the presence of sodium methoxide afforded 1,3-dimethyl-6,7,8,9-tetrahydrobenzofuro[3,2-d]pyrimidine-2,4-dione in 82% yield. The same substrate on treatment with cold cone. sulfuric acid at 0-5 degreesC for 2 h gave 1,3-dimethyl-5-oxabicyclo[3.3.1]nonano[3,2-d]pyrimidine-2,4-dione in 94% yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00656-1
• 作为产物：
  描述：

  5-羟基-1,3-二甲基嘧啶-2,4-二酮 在 氢氧化钾 、 pyridinium hydrobromide perbromide 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 13.5h， 生成 1,3-dimethyl-7,8,9,9a-tetrahydrobenzofuro[3,2-d]pyrimidine-2,4-dione
  参考文献：
  名称：

  Regioselective synthesis of pyrimidine annelated heterocycles from 6-(cyclohex-2-enyl)-1,3-dimethyl-5-hydroxyuracil

  摘要：

  6-(Cyclohex-2-enyl)-1,3-dimethyl-5-hydroxyuracil when treated with bromine in chloroform at 0-5 degreesC for 6 h furnishes 6-bromo-1,3-dimethylhexahydrobenzofuro[3,2-d]pyrimidine-2,4-dione in 80% yield. The same heterocycle is also obtained in 90% yield on treatment of the same substrate with pyridine hydrobromide perbromide for 30 min or with hexamethylenetetramine hydrotribromide for 15 min in methylene chloride at 0-5 degreesC. Cyclization of the same substrate with bis-benzonitrile palladium(II) chloride in benzene in the presence of sodium methoxide afforded 1,3-dimethyl-6,7,8,9-tetrahydrobenzofuro[3,2-d]pyrimidine-2,4-dione in 82% yield. The same substrate on treatment with cold cone. sulfuric acid at 0-5 degreesC for 2 h gave 1,3-dimethyl-5-oxabicyclo[3.3.1]nonano[3,2-d]pyrimidine-2,4-dione in 94% yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00656-1

文献信息

• Regioselective synthesis of pyrimidine annelated heterocycles from 6-(cyclohex-2-enyl)-1,3-dimethyl-5-hydroxyuracil
  作者：K.C. Majumdar、U. Das、U.K. Kundu、A. Bandyopadhyay

  DOI：10.1016/s0040-4020(01)00656-1

  日期：2001.8

  6-(Cyclohex-2-enyl)-1,3-dimethyl-5-hydroxyuracil when treated with bromine in chloroform at 0-5 degreesC for 6 h furnishes 6-bromo-1,3-dimethylhexahydrobenzofuro[3,2-d]pyrimidine-2,4-dione in 80% yield. The same heterocycle is also obtained in 90% yield on treatment of the same substrate with pyridine hydrobromide perbromide for 30 min or with hexamethylenetetramine hydrotribromide for 15 min in methylene chloride at 0-5 degreesC. Cyclization of the same substrate with bis-benzonitrile palladium(II) chloride in benzene in the presence of sodium methoxide afforded 1,3-dimethyl-6,7,8,9-tetrahydrobenzofuro[3,2-d]pyrimidine-2,4-dione in 82% yield. The same substrate on treatment with cold cone. sulfuric acid at 0-5 degreesC for 2 h gave 1,3-dimethyl-5-oxabicyclo[3.3.1]nonano[3,2-d]pyrimidine-2,4-dione in 94% yield. (C) 2001 Elsevier Science Ltd. All rights reserved.