6',7'-Dihydro-3',6'-dimethylspiro<1,3-dithiane-2,4'(5'H)benzofuran> | 131475-43-9

• 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: 6',7'-Dihydro-3',6'-dimethylspiro<1,3-dithiane-2,4'(5'H)benzofuran>
• 英文别名: 3',6'-dimethylspiro[1,3-dithiane-2,4'-6,7-dihydro-5H-1-benzofuran]
• CAS: 131475-43-9
• 化学式: C₁₃H₁₈OS₂
• 分子量: 254.417
• InChiKey: OZVNJYNLCYSTPG-UHFFFAOYSA-N

物化性质

• 沸点：
  378.6±42.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6',7'-Dihydro-3',6'-dimethylspiro<1,3-dithiane-2,4'(5'H)benzofuran> 在 镍 作用下， 以 乙醚 为溶剂， 反应 0.25h， 以55%的产率得到薄荷呋喃
  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：

  5-甲基环己烷-1,3-二酮 在 三氟化硼乙醚 、 sodium ethanolate 、 对甲苯磺酸 作用下， 以 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 5.0h， 生成 6',7'-Dihydro-3',6'-dimethylspiro<1,3-dithiane-2,4'(5'H)benzofuran>
  参考文献：
  名称：

  Aso, Mariko; Sakamoto, Mizue; Urakawa, Narumi, Heterocycles, 1990, vol. 31, # 6, p. 1003 - 1006

  摘要：

  DOI：

文献信息

• 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：——
• 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：——