3,6-Dimethylbenzofuran-4-ol | 131475-44-0

• 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: 3,6-Dimethylbenzofuran-4-ol
• 英文别名: 3,6-dimethyl-1-benzofuran-4-ol
• CAS: 131475-44-0
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: AZBSWJRPXCNZDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 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：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 3,6-Dimethylbenzofuran-4-ol
  参考文献：
  名称：

  Karrer et al., Helvetica Chimica Acta, 1921, vol. 4, p. 723

  摘要：

  DOI：

文献信息

• Foster et al., Journal of the Chemical Society, 1948, p. 2254,2258
  作者：Foster et al.

  DOI：——

  日期：——
• v. Pechmann; Hanke, Chemische Berichte, 1901, vol. 34, p. 356
  作者：v. Pechmann、Hanke

  DOI：——

  日期：——
• 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：——