3-(Hydroxymethyl)benzofuran-4,7-dione | 148587-53-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(Hydroxymethyl)benzofuran-4,7-dione
• 英文别名: 3-hydroxymethylbenzofuranquinone；3-(Hydroxymethyl)-1-benzofuran-4,7-dione
• CAS: 148587-53-5
• 化学式: C₉H₆O₄
• 分子量: 178.144
• InChiKey: CUDOHTROKYTDBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  67.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  间戊二烯 、 3-(Hydroxymethyl)benzofuran-4,7-dione 在 二异丙氧基二氯化钛 、 四氯苯醌 作用下， 生成 maturone 、 isomaturone
  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
• 作为产物：
  描述：

  Acetic acid 4-hydroxy-benzofuran-3-ylmethyl ester 在 KH₂PO₄ buffer 、 potassium nitrososulfonate 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 生成 3-(Hydroxymethyl)benzofuran-4,7-dione
  参考文献：
  名称：

  Aso, Mariko; Ojida, Akio; Yang, Guang, Heterocycles, 1993, vol. 35, # 1, p. 33 - 36

  摘要：

  DOI：

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; Ojida, Akio; Yang, Guang, Heterocycles, 1993, vol. 35, # 1, p. 33 - 36
  作者：Aso, Mariko、Ojida, Akio、Yang, Guang、Kanematsu, Ken

  DOI：——

  日期：——