2-(3-nitrophenyl)-2,3,6,7-tetrahydrobenzofuran-4(5H)-one

• 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: 2-(3-nitrophenyl)-2,3,6,7-tetrahydrobenzofuran-4(5H)-one
• 英文别名: 2-(3-nitrophenyl)-3,5,6,7-tetrahydro-2H-1-benzofuran-4-one
• 化学式: C₁₄H₁₃NO₄
• 分子量: 259.262
• InChiKey: NFYNCWAYYGQXOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3-环己二酮 在 dirhodium tetraacetate 、 potassium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.03h， 生成 1-(3-nitrophenyl)spiro[2.5]octa-4,8-dione 、 2-(3-nitrophenyl)-2,3,6,7-tetrahydrobenzofuran-4(5H)-one
  参考文献：
  名称：

  Metal-Catalyzed Thermal Reactions of Cyclic β-Dicarbonyl Phenyliodonium Ylide with Styrenes

  摘要：

  A cyclic beta-dicarbonyl phenyliodonium ylide reacted with various substituted styrenes under Rh-2(OAc)(4) catalysis to give cyclopropanes and dihydrofurans in a highly regioselective fashion. When styrenes with electron-donating substituents or disubstituted were employed, only dihydrofurans were isolated instead. A mechanism involving two competing pathways rationalizes the results.

  DOI：

  10.1021/jo502611x

文献信息

• Metal-Catalyzed Thermal Reactions of Cyclic β-Dicarbonyl Phenyliodonium Ylide with Styrenes
  作者：Alexandra-Eleni Bosnidou、Dimitra Kalpogiannaki、Sofia Karanestora、John A. Nixas、Lazaros P. Hadjiarapoglou

  DOI：10.1021/jo502611x

  日期：2015.1.16

  A cyclic beta-dicarbonyl phenyliodonium ylide reacted with various substituted styrenes under Rh-2(OAc)(4) catalysis to give cyclopropanes and dihydrofurans in a highly regioselective fashion. When styrenes with electron-donating substituents or disubstituted were employed, only dihydrofurans were isolated instead. A mechanism involving two competing pathways rationalizes the results.