5α-isobutyryloxysilphinen-3-one | 414896-80-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 5α-isobutyryloxysilphinen-3-one
• 英文别名: [(1R,5R,6S,8R,11R)-5,7,7,11-tetramethyl-4-oxo-6-tricyclo[6.3.0.01,5]undec-2-enyl] 2-methylpropanoate
• CAS: 414896-80-3
• 化学式: C₁₉H₂₈O₃
• 分子量: 304.43
• InChiKey: GAGHJRGICKXQAK-RUXMKHLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5α-isobutyryloxysilphinen-3-one 在 吡啶 、 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 5β-acetoxysilphinen-3-one
  参考文献：
  名称：

  C-5-Substituted Antifeedant Silphinene Sesquiterpenes from Senecio palmensis

  摘要：

  The new sesquiterpenes, 5alpha-senecioyloxysilphinen-3-one (5), 5alpha-tigloyloxysilphinen-3-one (7), and 3beta-hydroxy-5alpha-angeloyloxysilphinene (8), and the known compounds (6S)-2,10-bisaboladien-1-one (1), 6,7-epoxy-3(15)-caryophyllene (2), 6,7-epoxy-2,9-humuladiene (3), 5alpha-angeloyloxysilphinen-3-one (4), and 5alpha-acetoxysilphinen-3-one (6) were isolated from bioactive fractions of Senecio palmensis. The structures of these compounds were established by spectroscopic analysis and chemical evidence. The semisynthetic analogues silphinen-3,5-dione (9), 5alpha-hydroxysilphinen-3-one (10), 5beta-hydroxysilphinen-3-one (11), 5beta-acetoxysilphinen-3-one (12), and 5beta-isobutyryloxysilphinen-3-one (13) were generated to carry out a structure-activity study on the antifeedant action of these molecules against several divergent insect species.

  DOI：

  10.1021/np0105533
• 作为产物：
  描述：

  5α-angeloyloxysilphinen-3-one 在 吡啶 、 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 5α-isobutyryloxysilphinen-3-one
  参考文献：
  名称：

  C-5-Substituted Antifeedant Silphinene Sesquiterpenes from Senecio palmensis

  摘要：

  The new sesquiterpenes, 5alpha-senecioyloxysilphinen-3-one (5), 5alpha-tigloyloxysilphinen-3-one (7), and 3beta-hydroxy-5alpha-angeloyloxysilphinene (8), and the known compounds (6S)-2,10-bisaboladien-1-one (1), 6,7-epoxy-3(15)-caryophyllene (2), 6,7-epoxy-2,9-humuladiene (3), 5alpha-angeloyloxysilphinen-3-one (4), and 5alpha-acetoxysilphinen-3-one (6) were isolated from bioactive fractions of Senecio palmensis. The structures of these compounds were established by spectroscopic analysis and chemical evidence. The semisynthetic analogues silphinen-3,5-dione (9), 5alpha-hydroxysilphinen-3-one (10), 5beta-hydroxysilphinen-3-one (11), 5beta-acetoxysilphinen-3-one (12), and 5beta-isobutyryloxysilphinen-3-one (13) were generated to carry out a structure-activity study on the antifeedant action of these molecules against several divergent insect species.

  DOI：

  10.1021/np0105533