ethyl 5-iodo-7-methoxy-1-benzofuran-3-carboxylate | 1448158-31-3

• 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: ethyl 5-iodo-7-methoxy-1-benzofuran-3-carboxylate
• CAS: 1448158-31-3
• 化学式: C₁₂H₁₁IO₄
• 分子量: 346.121
• InChiKey: HHMYJBIBCBQGTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 5-iodo-7-methoxy-1-benzofuran-3-carboxylate 、 1-甲氧基-3-三甲基硅氧基-1,3-丁二烯 在 氟化铵 作用下， 以 甲苯 、 甲醇 为溶剂， 反应 22.0h， 生成 rac-ethyl (5aS,9S,9aS)-2-iodo-4,9-dimethoxy-7-oxo-5a,6,7,8,9,9a-hexahydrodibenzo[b,d]furan-9a-carboxylate 、 rac-ethyl (5aS,9R,9aS)-2-iodo-4,9-dimethoxy-7-oxo-5a,6,7,8,9,9a-hexahydrodibenzo[b,d]furan-9a-carboxylate
  参考文献：
  名称：

  Diels-alder reactions with ethyl 1-benzofuran-3-carboxylates

  摘要：

  Substituted salicylaldehydes reacted with ethyl diazoacetate to give ethyl 1-benzofuran-3-carboxylates containing various substituents in the aromatic ring. The Diels-Alder reaction of these compounds with Danishefsky's diene was regioselective, and it provided an effective method for the construction of the heterocyclic skeleton of hexahydrodibenzo[b,d]furan-7-one or tetrahydrodibenzo[b,d]furan-7-one. The adducts were found to undergo rearrangement to substituted 4'-hydroxybiphenyl-2-yl methyl carbonates during column chromatography on silica gel.

  DOI：

  10.1134/s1070428013060134
• 作为产物：
  描述：

  在 硫酸 作用下， 反应 0.17h， 以1.00 g的产率得到ethyl 5-iodo-7-methoxy-1-benzofuran-3-carboxylate
  参考文献：
  名称：

  Diels-alder reactions with ethyl 1-benzofuran-3-carboxylates

  摘要：

  Substituted salicylaldehydes reacted with ethyl diazoacetate to give ethyl 1-benzofuran-3-carboxylates containing various substituents in the aromatic ring. The Diels-Alder reaction of these compounds with Danishefsky's diene was regioselective, and it provided an effective method for the construction of the heterocyclic skeleton of hexahydrodibenzo[b,d]furan-7-one or tetrahydrodibenzo[b,d]furan-7-one. The adducts were found to undergo rearrangement to substituted 4'-hydroxybiphenyl-2-yl methyl carbonates during column chromatography on silica gel.

  DOI：

  10.1134/s1070428013060134