3,6-Dimethylbenzofuran-4,7-dione | 131475-45-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,6-Dimethylbenzofuran-4,7-dione
• 英文别名: 3,6-Dimethyl-1-benzofuran-4,7-dione
• CAS: 131475-45-1
• 化学式: C₁₀H₈O₃
• 分子量: 176.172
• InChiKey: MLPOFINHGBTSGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  47.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(tert-butyldimethylsilyloxy)-1-methoxy-1,3-butadiene 、 3,6-Dimethylbenzofuran-4,7-dione 以 甲苯 为溶剂， 反应 12.0h， 以80%的产率得到(4aβ,8α,8aβ)-6-(tert-Butyldimethylsiloxy)-8-methoxy-3,8a-dimethyl-4a,5,8,8a-tetrahydronaphtho<2,3-b>furan-4,9-dione
  参考文献：
  名称：

  Total Syntheses of Marine Furanosesquiterpenoids, Tubipofurans

  摘要：

  The first total syntheses of marine furanosesquiterpenoids, tubipofuran (1) and 15-acetoxytubipofuran (2), have been achieved via the common intermediate 3. The syntheses were begun by our newly improved fused 3-methylfuran construction method by the reaction of allenic sulfonium salt with the enolate anion of a cyclic 1,3-diketone. Using this fused furan synthesis, multigram quantities of bicyclic 3-methylfurans were readily obtained in only one step. The cis-fused furanodecalin system was constructed by the regioselective Diels-Alder reaction of benzofuran-quinone 5 and Danishefsky diene 4. The Diels-Alder adduct 9 was transformed into the intermediate 3 by sequential radical deoxygenations of the two hydroxy groups derived from benzofuranquinone 5.

  DOI：

  10.1021/jo00099a028
• 作为产物：
  描述：

  3,6-Dimethylbenzofuran-4-ol 在 potassium dihydrogenphosphate 、 potassium nitrososulfonate 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以69%的产率得到3,6-Dimethylbenzofuran-4,7-dione
  参考文献：
  名称：

  Furannulation strategy for synthesis of the naturally occurring fused 3-methylfurans: efficient synthesis of evodone and menthofuran and regioselective synthesis of maturone via a Lewis acid catalyzed Diels-Alder reactions. Some comments for its mechanistic aspects

  摘要：

  Fused 3-methylfurans are readily obtained by the reaction of allenic sulfonium salt 1 and the enolate anions of cyclic 1,3-dicarbonyl compounds in two steps. Using these fused 3-methylfuran compounds as intermediates, furanoterpenoids such as menthofuran (8) and evodone (4b) are synthesized efficiently. Moreover, maturone (15) is also obtained regioselectivity by Lewis acid CatalYzed Diels-Alder reaction of benzofuranquinone (12) with piperylene. In the context with the regioselectivity observed in the Diels-Alder reaction of 12, semiempirical molecular orbital calculations are applied to gain its theoretical interpretation based upon frontier molecular orbital theory and transition state analysis.

  DOI：

  10.1021/jo00067a031

文献信息

• Furannulation strategy for synthesis of the naturally occurring fused 3-methylfurans: efficient synthesis of evodone and menthofuran and regioselective synthesis of maturone via a Lewis acid catalyzed Diels-Alder reactions. Some comments for its mechanistic aspects
  作者：Mariko Aso、Akio Ojida、Guang Yang、Ok Ja Cha、Eiji Osawa、Ken Kanematsu

  DOI：10.1021/jo00067a031

  日期：1993.7

  Fused 3-methylfurans are readily obtained by the reaction of allenic sulfonium salt 1 and the enolate anions of cyclic 1,3-dicarbonyl compounds in two steps. Using these fused 3-methylfuran compounds as intermediates, furanoterpenoids such as menthofuran (8) and evodone (4b) are synthesized efficiently. Moreover, maturone (15) is also obtained regioselectivity by Lewis acid CatalYzed Diels-Alder reaction of benzofuranquinone (12) with piperylene. In the context with the regioselectivity observed in the Diels-Alder reaction of 12, semiempirical molecular orbital calculations are applied to gain its theoretical interpretation based upon frontier molecular orbital theory and transition state analysis.
• Aso, Mariko; Sakamoto, Mizue; Urakawa, Narumi, Heterocycles, 1990, vol. 31, # 6, p. 1003 - 1006
  作者：Aso, Mariko、Sakamoto, Mizue、Urakawa, Narumi、Kanematsu, Ken

  DOI：——

  日期：——
• ASO, MARIKO;SAKAMOTO, MIZUE;URAKAWA, NARUMI;KANEMATSU, KEN, HETEROCYCLES, 31,(1990) N, C. 1003-1006
  作者：ASO, MARIKO、SAKAMOTO, MIZUE、URAKAWA, NARUMI、KANEMATSU, KEN

  DOI：——

  日期：——
• Total Syntheses of Marine Furanosesquiterpenoids, Tubipofurans
  作者：Akio Ojida、Fumiyo Tanoue、Ken Kanematsu

  DOI：10.1021/jo00099a028

  日期：1994.10

  The first total syntheses of marine furanosesquiterpenoids, tubipofuran (1) and 15-acetoxytubipofuran (2), have been achieved via the common intermediate 3. The syntheses were begun by our newly improved fused 3-methylfuran construction method by the reaction of allenic sulfonium salt with the enolate anion of a cyclic 1,3-diketone. Using this fused furan synthesis, multigram quantities of bicyclic 3-methylfurans were readily obtained in only one step. The cis-fused furanodecalin system was constructed by the regioselective Diels-Alder reaction of benzofuran-quinone 5 and Danishefsky diene 4. The Diels-Alder adduct 9 was transformed into the intermediate 3 by sequential radical deoxygenations of the two hydroxy groups derived from benzofuranquinone 5.