3-ethyl-2-thioxo-2,3-dihydrobenzofuro[3,2-d]pyrimidin-4(1H)-one | 1233397-53-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3-ethyl-2-thioxo-2,3-dihydrobenzofuro[3,2-d]pyrimidin-4(1H)-one
• CAS: 1233397-53-9
• 化学式: C₁₂H₁₀N₂O₂S
• 分子量: 246.29
• InChiKey: HTDSEGWLZCNLRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  50.93
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-(2-(bromomethyl)phenyl)-3-methoxyacrylate 、 3-ethyl-2-thioxo-2,3-dihydrobenzofuro[3,2-d]pyrimidin-4(1H)-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以88%的产率得到methyl (2E)-3-methoxy-2-(2-{[(3-ethyl-4-oxo-3,4-dihydrobenzofuro[3,2-d]pyrimidin-2-yl)thio]methyl}phenyl)acrylate
  参考文献：
  名称：

  Efficient Synthesis and Fungicidal Activities of 2-Alkylthiobenzofuro[3,2-d]Pyrimidinones

  摘要：

  2-Alkylthiobenzofuro[3,2-d]pyrimidinones 5 and 6 were synthesized by S-alkylation of 2,3-dihydro-2-thioxobenzofuro[3,2-d]pyrimidin-4(1H)-ones 4, which were obtained via aza-Wittig reaction of iminophosphorane 2 with CS2 and further reaction of the product with various amines. Compounds 5 and 6 exhibited fungicidal activity. For example, compound 6a, which has a small N-substituted methyl group, showed the best inhibitive activity (91%) against Dothiorella gregaria at 50 mg/L. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

  DOI：

  10.1080/10426500903008922
• 作为产物：
  描述：

  ethyl 3-isothiocyanato-1-benzofuran-2-carboxylate 、 乙胺 以 乙腈 为溶剂， 反应 0.5h， 以86%的产率得到3-ethyl-2-thioxo-2,3-dihydrobenzofuro[3,2-d]pyrimidin-4(1H)-one
  参考文献：
  名称：

  Efficient Synthesis and Fungicidal Activities of 2-Alkylthiobenzofuro[3,2-d]Pyrimidinones

  摘要：

  2-Alkylthiobenzofuro[3,2-d]pyrimidinones 5 and 6 were synthesized by S-alkylation of 2,3-dihydro-2-thioxobenzofuro[3,2-d]pyrimidin-4(1H)-ones 4, which were obtained via aza-Wittig reaction of iminophosphorane 2 with CS2 and further reaction of the product with various amines. Compounds 5 and 6 exhibited fungicidal activity. For example, compound 6a, which has a small N-substituted methyl group, showed the best inhibitive activity (91%) against Dothiorella gregaria at 50 mg/L. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

  DOI：

  10.1080/10426500903008922