Methyl (+/-)-3-<(1R*,2R*,3S*,4R*)-1-Cyano-3,4-dimethyl-1-<(1E,3Z)-4-(phenylthio)butadien-1-yl>-3-vinylcyclohex-2-yl>propionate

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: Methyl (+/-)-3-<(1R*,2R*,3S*,4R*)-1-Cyano-3,4-dimethyl-1-<(1E,3Z)-4-(phenylthio)butadien-1-yl>-3-vinylcyclohex-2-yl>propionate
• 英文别名: methyl 3-[(1R,2S,3R,6R)-6-cyano-2-ethenyl-2,3-dimethyl-6-[(1E,3Z)-4-phenylsulfanylbuta-1,3-dienyl]cyclohexyl]propanoate
• 化学式: C₂₅H₃₁NO₂S
• 分子量: 409.593
• InChiKey: BLJDDIXRIKWPEF-IDOWXRKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl (+/-)-3-<(1R*,2R*,3S*,4R*)-1-Cyano-3,4-dimethyl-1-<(1E,3Z)-4-(phenylthio)butadien-1-yl>-3-vinylcyclohex-2-yl>propionate 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以89%的产率得到(+/-)-3-<(1S*,2R*,3S*,4R*)-1-Cyano-3,4-dimethyl-1-<(1E,3Z)-4-(phenylthio)butadien-1-yl>-3-vinylcyclohex-2-yl>-1-propanol
  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
• 作为产物：
  描述：

  (+/-)-5,6-Dimethyl-2,3,4,4a,5,6,7,8-octahydro-2-oxo-5-vinylnaphthalene 在 lead(IV) acetate 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 硫酸 、 一水合肼 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 为溶剂， 反应 30.33h， 生成 Methyl (+/-)-3-<(1R*,2R*,3S*,4R*)-1-Cyano-3,4-dimethyl-1-<(1E,3Z)-4-(phenylthio)butadien-1-yl>-3-vinylcyclohex-2-yl>propionate
  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.