4-nitronaphtho<1,2-b>furan-6,9-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 4-nitronaphtho<1,2-b>furan-6,9-dione
• 英文别名: 4-Nitrobenzo[g][1]benzofuran-6,9-dione
• 化学式: C₁₂H₅NO₅
• 分子量: 243.175
• InChiKey: PGOOVXRVHCAUKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  93.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  cis-3a,9b-dihydro-6,9-dihydroxy-4-nitronaphtho<1,2-b>furan 在 manganese(IV) oxide 作用下， 以 苯 为溶剂， 反应 2.0h， 以53%的产率得到4-nitronaphtho<1,2-b>furan-6,9-dione
  参考文献：
  名称：

  Synthesis of Angular Quinoid Heterocycles from 2-(2-Nitrovinyl)-1,4-benzoquinone

  摘要：

  Reactions of 2-(2-nitrovinyl)-1,4-benzoquinone with furans, indoles, and endocyclic enol ethers form angular fused heterocyclic quinoid ring systems. The reaction proceeds by a formal inverse electron-demand [4 + 2] cycloaddition reaction of the nitrovinylquinone and a double bond of the heterocycle. The initial quinoid cycloadducts can be readily tautomerized to hydroquinoid species, which may be dehydrogenated to fully aromatic quinones. In the case of furans, the tautomerized adducts may be ring-opened to give 6,7-di- or 5,6,7-tri-substituted-1,4-naphthalenediols. In the case of endocyclic enol ethers, formation of benzofuran products competes with [4 + 2] cycloaddition.

  DOI：

  10.1021/jo981899u

文献信息

• Synthesis of Angular Quinoid Heterocycles from 2-(2-Nitrovinyl)-1,4-benzoquinone
  作者：Wayland E. Noland、Brant L. Kedrowski

  DOI：10.1021/jo981899u

  日期：1999.1.1

  Reactions of 2-(2-nitrovinyl)-1,4-benzoquinone with furans, indoles, and endocyclic enol ethers form angular fused heterocyclic quinoid ring systems. The reaction proceeds by a formal inverse electron-demand [4 + 2] cycloaddition reaction of the nitrovinylquinone and a double bond of the heterocycle. The initial quinoid cycloadducts can be readily tautomerized to hydroquinoid species, which may be dehydrogenated to fully aromatic quinones. In the case of furans, the tautomerized adducts may be ring-opened to give 6,7-di- or 5,6,7-tri-substituted-1,4-naphthalenediols. In the case of endocyclic enol ethers, formation of benzofuran products competes with [4 + 2] cycloaddition.