3-(Methoxymethoxymethyl)-6,7-dihydrobenzofuran-4(5H)-one | 149705-59-9

• 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-(Methoxymethoxymethyl)-6,7-dihydrobenzofuran-4(5H)-one
• 英文别名: 3-(methoxymethoxymethyl)-6,7-dihydro-5H-1-benzofuran-4-one
• CAS: 149705-59-9
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: VONZUQOAYSWLMU-UHFFFAOYSA-N

物化性质

• 沸点：
  306.5±42.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯亚硫酸甲酯 、 3-(Methoxymethoxymethyl)-6,7-dihydrobenzofuran-4(5H)-one 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 5-Benzenesulfinyl-3-methoxymethoxymethyl-6,7-dihydro-5H-benzofuran-4-one
  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：

  3-methylidene-6,7-dihydro-5H-1-benzofuran-4-one 在 N-溴代丁二酰亚胺(NBS) 、 四丁基碘化铵 、 magnesium monoperoxyphthalate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 22.5h， 生成 3-(Methoxymethoxymethyl)-6,7-dihydrobenzofuran-4(5H)-one
  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