4-oxo-4,5,6,7-tetrahydrobenzofuran-7-carboxylic acid methyl ester | 174676-67-6

• 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: 4-oxo-4,5,6,7-tetrahydrobenzofuran-7-carboxylic acid methyl ester
• 英文别名: methyl 4-oxo-6,7-dihydro-5H-1-benzofuran-7-carboxylate
• CAS: 174676-67-6
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: BZYYZLHPKGICLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-oxo-4,5,6,7-tetrahydrobenzofuran-7-carboxylic acid methyl ester 在 palladium on activated charcoal 作用下， 以 二苯醚 为溶剂， 以70%的产率得到4-hydroxybenzofuran-7-carboxylic acid methyl ester
  参考文献：
  名称：

  Site Selectivity of the Diels−Alder Reactions of 3-[1-(tert-Butyldimethylsilyloxy)vin-1-yl]furan and 3-(Propen-2-yl)furan. Synthesis of 4-Substituted Benzofurans

  摘要：

  The Diels-Alder reaction of 5-vinylfurans 5 and 27 with DMAD, N-phenylmaleimide, and dimethyl maleate afforded products derived both from addition to the furan ring diene system (intraannular addition) and to the furan 2,3-double bond 3-vinyl group diene system (extraannular addition). For example, compounds 6 and 7 were obtained from 5 and DMAD. In contrast, dienophiles containing a phenylsulfinyl group, such as 19-21, gave products derived exclusively from the extraannular reaction mode. These products are useful precursors of 4-substituted benzofurans, especially 4-hydroxybenzofurans.

  DOI：

  10.1021/jo951546k
• 作为产物：
  描述：

  1-呋喃-3-乙酮 在 三乙胺 、 对苯二酚 、 zinc(II) chloride 作用下， 以 甲苯 、 苯 为溶剂， 反应 12.0h， 生成 4-oxo-4,5,6,7-tetrahydrobenzofuran-7-carboxylic acid methyl ester
  参考文献：
  名称：

  Site Selectivity of the Diels−Alder Reactions of 3-[1-(tert-Butyldimethylsilyloxy)vin-1-yl]furan and 3-(Propen-2-yl)furan. Synthesis of 4-Substituted Benzofurans

  摘要：

  The Diels-Alder reaction of 5-vinylfurans 5 and 27 with DMAD, N-phenylmaleimide, and dimethyl maleate afforded products derived both from addition to the furan ring diene system (intraannular addition) and to the furan 2,3-double bond 3-vinyl group diene system (extraannular addition). For example, compounds 6 and 7 were obtained from 5 and DMAD. In contrast, dienophiles containing a phenylsulfinyl group, such as 19-21, gave products derived exclusively from the extraannular reaction mode. These products are useful precursors of 4-substituted benzofurans, especially 4-hydroxybenzofurans.

  DOI：

  10.1021/jo951546k