(+/-)-(4aR*,5S*,6R*,8aS*)-8a-(Acetoxymethyl)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,6-dimethyl-2,2-(ethylenedioxy)-5-vinylnaphthalene

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-(4aR*,5S*,6R*,8aS*)-8a-(Acetoxymethyl)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,6-dimethyl-2,2-(ethylenedioxy)-5-vinylnaphthalene
• 英文别名: [(4'aR,7'R,8'S,8'aR)-8'-ethenyl-7',8'-dimethylspiro[1,3-dioxolane-2,3'-2,4,5,6,7,8a-hexahydro-1H-naphthalene]-4'a-yl]methyl acetate
• 化学式: C₁₉H₃₀O₄
• 分子量: 322.445
• InChiKey: BCBCLZWKLAKEJV-BGTYHANMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (+/-)-5,6-Dimethyl-2,3,4,4a,5,6,7,8-octahydro-2-oxo-5-vinylnaphthalene 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 高氯酸 、 silica gel 、 二异丁基氢化铝 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 42.0h， 生成 (+/-)-(4aR*,5S*,6R*,8aS*)-8a-(Acetoxymethyl)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,6-dimethyl-2,2-(ethylenedioxy)-5-vinylnaphthalene
  参考文献：
  名称：

  Stereoselective Construction of the Diterpene Part of Indole Alkaloids, Radarins, by Way of Intramolecular Diels-Alder Reaction

  摘要：

  The tricyclic diterpene part of the indole alkaloids, radarins A-D (1-4), was synthesized in a highly stereoselective manner by the exploitation of an intramolecular Diels-Alder reaction. (+/-)-5,6-Dimethyl-2,3,4,4a,5,6,7,8-octahydro-2-oxo-5-vinylnaphthalene (7) was converted into trienes 28 and 29, possessing (1E,3E)- and (1E,3Z)-4-(phenylthio)butadiene moieties. Intramolecular [4 + 2] cycloadditions of 28 and 29 yielded tricyclic 32 selectively, producing the ABC carbon skeleton of radarins.

  DOI：

  10.1021/jo00122a042

文献信息

• Stereoselective Construction of the Diterpene Part of Indole Alkaloids, Radarins, by Way of Intramolecular Diels-Alder Reaction
  作者：Masataka Ihara、Akira Katsumata、Michiko Egashira、Shuichi Suzuki、Yuji Tokunaga、Keiichiro Fukumoto

  DOI：10.1021/jo00122a042

  日期：1995.9

  The tricyclic diterpene part of the indole alkaloids, radarins A-D (1-4), was synthesized in a highly stereoselective manner by the exploitation of an intramolecular Diels-Alder reaction. (+/-)-5,6-Dimethyl-2,3,4,4a,5,6,7,8-octahydro-2-oxo-5-vinylnaphthalene (7) was converted into trienes 28 and 29, possessing (1E,3E)- and (1E,3Z)-4-(phenylthio)butadiene moieties. Intramolecular [4 + 2] cycloadditions of 28 and 29 yielded tricyclic 32 selectively, producing the ABC carbon skeleton of radarins.