(5aα,9aβ)-3-Methyl-5a,6,7,8,9,9a-hexahydronaphtho<1,2-b>furan-4(5H)one | 131475-42-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: (5aα,9aβ)-3-Methyl-5a,6,7,8,9,9a-hexahydronaphtho<1,2-b>furan-4(5H)one
• 英文别名: (5aS,9aR)-3-methyl-5a,6,7,8,9,9a-hexahydro-5H-benzo[g][1]benzofuran-4-one
• CAS: 131475-42-8
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: GKMGFVICPDJXPI-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  Allenyldimethylsulfonium bromide 、 六氢萘-1,3-二酮 生成 (5aα,9aβ)-3-Methyl-5a,6,7,8,9,9a-hexahydronaphtho<1,2-b>furan-4(5H)one
  参考文献：
  名称：

  ASO, MARIKO;SAKAMOTO, MIZUE;URAKAWA, NARUMI;KANEMATSU, KEN, HETEROCYCLES, 31,(1990) N, C. 1003-1006

  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; 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：——