1,5-dihydro-1,3-dimethyl-5-thienyl-2H-pyrano[2,3-d]pyrimidine-2,4(3H)-dione | 1160635-83-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃嘧啶类
• 英文名称: 1,5-dihydro-1,3-dimethyl-5-thienyl-2H-pyrano[2,3-d]pyrimidine-2,4(3H)-dione
• 英文别名: 1,5-Dihydro-1,3-dimethyl-5-thienyl-2h-pyrano[2,3-d]-pyrimidine-2,4(3h)-dione；1,3-dimethyl-5-thiophen-2-yl-5H-pyrano[2,3-d]pyrimidine-2,4-dione
• CAS: 1160635-83-5
• 化学式: C₁₃H₁₂N₂O₃S
• 分子量: 276.316
• InChiKey: MSYMZDJQWPNCNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  78.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙烯基乙醚 、 1,3-dimethyl-5-(thiophen-2-ylmethylene)pyrimidine-2,4,6(1H,3H,5H)-trione 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 1,5-dihydro-1,3-dimethyl-5-thienyl-2H-pyrano[2,3-d]pyrimidine-2,4(3H)-dione 、 (5RS,7RS)-7-ethoxy-1,5,6,7-tetrahydro-1,3-dimethyl-5-(2-thienyl)-2H-pyrano[2,3-d]pyrimidine-2,4(3H)-dione 、 (5RS,7SR)-7-ethoxy-1,5,6,7-tetrahydro-1,3-dimethyl-5-(2-thienyl)-2H-pyrano[2,3-d]pyrimidine-2,4(3H)-dione
  参考文献：
  名称：

  Three-component one-pot synthesis of fused uracils – pyrano[2,3-d]‐pyrimidine-2,4-diones

  摘要：

  5-Arylidene-N,N-dimethylbarbituric acids undergo smooth hetero-Diels-Alder reactions with enol ethers to afford cis and trans diastereoisomers of 7-alkoxy-5-aryl-2H-pyrano[2,3-d]pyrimidine-2,4-diones in excellent yields (84-95%). Cycloadducts with cis-configuration were the major products. Three-component one-pot reactions of N,N-dimethylbarbituric acid, aromatic and heteroaromatic aldehydes, and enol ethers in the presence of piperidine gave uracils also in very good yields (87-95%). The structure of the cycloadducts is discussed in terms of configuration and preferred conformation.

  DOI：

  10.1007/s00706-008-0935-z

文献信息

• Three-component one-pot synthesis of fused uracils – pyrano[2,3-d]‐pyrimidine-2,4-diones
  作者：Aleksandra Pałasz

  DOI：10.1007/s00706-008-0935-z

  日期：2008.11

  5-Arylidene-N,N-dimethylbarbituric acids undergo smooth hetero-Diels-Alder reactions with enol ethers to afford cis and trans diastereoisomers of 7-alkoxy-5-aryl-2H-pyrano[2,3-d]pyrimidine-2,4-diones in excellent yields (84-95%). Cycloadducts with cis-configuration were the major products. Three-component one-pot reactions of N,N-dimethylbarbituric acid, aromatic and heteroaromatic aldehydes, and enol ethers in the presence of piperidine gave uracils also in very good yields (87-95%). The structure of the cycloadducts is discussed in terms of configuration and preferred conformation.