N-(3a-cyano-2,3,3a,6a-tetrahydro-5-phenylfuro[2,3-b]furan-6a-yl)acetamide | 1210055-67-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: N-(3a-cyano-2,3,3a,6a-tetrahydro-5-phenylfuro[2,3-b]furan-6a-yl)acetamide
• 英文别名: N-(3a-cyano-5-phenyl-2,3-dihydrofuro[2,3-b]furan-6a-yl)acetamide
• CAS: 1210055-67-6
• 化学式: C₁₅H₁₄N₂O₃
• 分子量: 270.288
• InChiKey: QBSCLUCUXMJSJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酸酐 、 3-cyano-2-imino-3-phenacyltetrahydrofuran 反应 3.0h， 以89%的产率得到N-(3a-cyano-2,3,3a,6a-tetrahydro-5-phenylfuro[2,3-b]furan-6a-yl)acetamide
  参考文献：
  名称：

  A Simple Approach to the Synthesis of Furofurans and Furopyrroles Using 3-Phenacylated Tetrahydro-2-imino-3-furancarbonitriles

  摘要：

  A new and easy synthetic route to furo[2,3-b]furans 7a-d and furo[2,3-b]pyrroles 8a-d has been achieved by the C-phenacylation/cyclization reactions of 2-amino-4,5-dihydro-3-furancarbonitrile (5). Thermal treatment of the key intermediate 3-phenacylated tetrahydro-2-imino-3-furancarbonitriles 6a-d, which were prepared from compound 5 and phenacyl bromides, e.g. phenacyl bromide, 4-chlorophenacyl bromide, 4-methylphenacyl bromide and 4-methoxyphenacyl bromide, with acetic anhydride caused intramolecular cyclization to yield the corresponding furo[2,3-b]furans 7a-d. On the other hand, methanolic sodium methoxide-assisted cyclocondensation of compounds 6a-d gave the corresponding furo[2,3-b]pyrroles 8a-d.

  DOI：

  10.3987/com-09-s(s)48