(4aβ,8aβ)-3,8a-Dimethyl-4,4a,8a,9-tetrahydronaphtho<2,3-b>furan-6(5H)-one

• 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: (4aβ,8aβ)-3,8a-Dimethyl-4,4a,8a,9-tetrahydronaphtho<2,3-b>furan-6(5H)-one
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: RPRMYUWFOPEHGP-IINYFYTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  30.21
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (4aβ,8aβ)-3,8a-Dimethyl-4,4a,8a,9-tetrahydronaphtho<2,3-b>furan-6(5H)-one 在 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.67h， 生成 3,5,8-Trimethyl-4,4a,5,6,8a,9-hexahydronaphtho<2,3-b>furan-6-ol
  参考文献：
  名称：

  Total Syntheses of Marine Furanosesquiterpenoids, Tubipofurans

  摘要：

  The first total syntheses of marine furanosesquiterpenoids, tubipofuran (1) and 15-acetoxytubipofuran (2), have been achieved via the common intermediate 3. The syntheses were begun by our newly improved fused 3-methylfuran construction method by the reaction of allenic sulfonium salt with the enolate anion of a cyclic 1,3-diketone. Using this fused furan synthesis, multigram quantities of bicyclic 3-methylfurans were readily obtained in only one step. The cis-fused furanodecalin system was constructed by the regioselective Diels-Alder reaction of benzofuran-quinone 5 and Danishefsky diene 4. The Diels-Alder adduct 9 was transformed into the intermediate 3 by sequential radical deoxygenations of the two hydroxy groups derived from benzofuranquinone 5.

  DOI：

  10.1021/jo00099a028
• 作为产物：
  描述：

  在 盐酸 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.33h， 生成 (4aβ,8aβ)-3,8a-Dimethyl-4,4a,8a,9-tetrahydronaphtho<2,3-b>furan-6(5H)-one
  参考文献：
  名称：

  Total Syntheses of Marine Furanosesquiterpenoids, Tubipofurans

  摘要：

  The first total syntheses of marine furanosesquiterpenoids, tubipofuran (1) and 15-acetoxytubipofuran (2), have been achieved via the common intermediate 3. The syntheses were begun by our newly improved fused 3-methylfuran construction method by the reaction of allenic sulfonium salt with the enolate anion of a cyclic 1,3-diketone. Using this fused furan synthesis, multigram quantities of bicyclic 3-methylfurans were readily obtained in only one step. The cis-fused furanodecalin system was constructed by the regioselective Diels-Alder reaction of benzofuran-quinone 5 and Danishefsky diene 4. The Diels-Alder adduct 9 was transformed into the intermediate 3 by sequential radical deoxygenations of the two hydroxy groups derived from benzofuranquinone 5.

  DOI：

  10.1021/jo00099a028

文献信息

• Total Syntheses of Marine Furanosesquiterpenoids, Tubipofurans
  作者：Akio Ojida、Fumiyo Tanoue、Ken Kanematsu

  DOI：10.1021/jo00099a028

  日期：1994.10

  The first total syntheses of marine furanosesquiterpenoids, tubipofuran (1) and 15-acetoxytubipofuran (2), have been achieved via the common intermediate 3. The syntheses were begun by our newly improved fused 3-methylfuran construction method by the reaction of allenic sulfonium salt with the enolate anion of a cyclic 1,3-diketone. Using this fused furan synthesis, multigram quantities of bicyclic 3-methylfurans were readily obtained in only one step. The cis-fused furanodecalin system was constructed by the regioselective Diels-Alder reaction of benzofuran-quinone 5 and Danishefsky diene 4. The Diels-Alder adduct 9 was transformed into the intermediate 3 by sequential radical deoxygenations of the two hydroxy groups derived from benzofuranquinone 5.