3,3a,4,6a-tetrahydro-6a-methoxy-5-phenylfuro[2,3-b]pyrrole-3a(2H)-carbonitrile | 1210055-71-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3a,4,6a-tetrahydro-6a-methoxy-5-phenylfuro[2,3-b]pyrrole-3a(2H)-carbonitrile
• 英文别名: 6a-methoxy-5-phenyl-3,4-dihydro-2H-furo[2,3-b]pyrrole-3a-carbonitrile
• CAS: 1210055-71-2
• 化学式: C₁₄H₁₄N₂O₂
• 分子量: 242.277
• InChiKey: OZRZYTNFBLHWTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  54.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  sodium methylate 、 3-cyano-2-imino-3-phenacyltetrahydrofuran 以 甲醇 为溶剂， 反应 2.0h， 以65%的产率得到3,3a,4,6a-tetrahydro-6a-methoxy-5-phenylfuro[2,3-b]pyrrole-3a(2H)-carbonitrile
  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