[(E,6R)-6-hydroxy-2-methyl-5-oxo-6-[(2S,8S,9R,10R,13R,14S,17S)-4,4,9,13,14-pentamethyl-2-(4-methylphenyl)sulfonyloxy-3,11,16-trioxo-1,2,7,8,10,12,15,17-octahydrocyclopenta[a]phenanthren-17-yl]hept-3-en-2-yl] acetate | 1440419-72-6

• 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: [(E,6R)-6-hydroxy-2-methyl-5-oxo-6-[(2S,8S,9R,10R,13R,14S,17S)-4,4,9,13,14-pentamethyl-2-(4-methylphenyl)sulfonyloxy-3,11,16-trioxo-1,2,7,8,10,12,15,17-octahydrocyclopenta[a]phenanthren-17-yl]hept-3-en-2-yl] acetate
• CAS: 1440419-72-6
• 化学式: C₃₉H₅₀O₁₀S
• 分子量: 710.886
• InChiKey: IIAMMJHSVGOEET-MNLUEQDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  50
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  167
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(E,6R)-6-hydroxy-2-methyl-5-oxo-6-[(2S,8S,9R,10R,13R,14S,17S)-4,4,9,13,14-pentamethyl-2-(4-methylphenyl)sulfonyloxy-3,11,16-trioxo-1,2,7,8,10,12,15,17-octahydrocyclopenta[a]phenanthren-17-yl]hept-3-en-2-yl] acetate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Chemical Modification Produces Species-Specific Changes in Cucurbitacin Antifeedant Effect

  摘要：

  Cucurbitacins are secondary metabolites that mediate insect plant interactions not only as allomones against generalists but also as kairomones for specialist herbivores. This study was undertaken to identify the potential of cucurbitacin derivatives as insect antifeedant agents. The antifeedant capacity against a Cucurbitaceae specialist [Epilachna paenulata (Coleoptera: Coccinellidae)] and a polyphagous insect [Pseudaletia adultera (Lepidoptera: Noctuidae)] was evaluated in preference tests in which the insects were given a choice between food plants either treated with the cucurbitacin derivatives or treated with the solvent. The activity was found not to be related to the basic cucurbitacin skeleton, as only IS of the 28 tested cucurbitacin derivatives were active. Only one of the tested compounds was phagostimulant to the specialist insect (the hemissuccinate of 16-oxo-dihydrocucurbitacin B derivative), while all other active derivatives were deterrent against one of the insects (13 compounds) or both of them (3 compounds). Changes in ring A of the cucurbitacins, as well as in the side chain, modified the activity. As a general trend, when chemical modifications of the basic structure produced a change in activity, the response was opposite in both insects used as biodetectors, indicating that a selective variation in the activity may be achieved by chemical modifications of the cucurbitacin skeleton.

  DOI：

  10.1021/jf4002457
• 作为产物：
  描述：

  葫芦素 B 在 三乙烯二胺 、 barium carbonate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 [(E,6R)-6-hydroxy-2-methyl-5-oxo-6-[(2S,8S,9R,10R,13R,14S,17S)-4,4,9,13,14-pentamethyl-2-(4-methylphenyl)sulfonyloxy-3,11,16-trioxo-1,2,7,8,10,12,15,17-octahydrocyclopenta[a]phenanthren-17-yl]hept-3-en-2-yl] acetate
  参考文献：
  名称：

  Chemical Modification Produces Species-Specific Changes in Cucurbitacin Antifeedant Effect

  摘要：

  Cucurbitacins are secondary metabolites that mediate insect plant interactions not only as allomones against generalists but also as kairomones for specialist herbivores. This study was undertaken to identify the potential of cucurbitacin derivatives as insect antifeedant agents. The antifeedant capacity against a Cucurbitaceae specialist [Epilachna paenulata (Coleoptera: Coccinellidae)] and a polyphagous insect [Pseudaletia adultera (Lepidoptera: Noctuidae)] was evaluated in preference tests in which the insects were given a choice between food plants either treated with the cucurbitacin derivatives or treated with the solvent. The activity was found not to be related to the basic cucurbitacin skeleton, as only IS of the 28 tested cucurbitacin derivatives were active. Only one of the tested compounds was phagostimulant to the specialist insect (the hemissuccinate of 16-oxo-dihydrocucurbitacin B derivative), while all other active derivatives were deterrent against one of the insects (13 compounds) or both of them (3 compounds). Changes in ring A of the cucurbitacins, as well as in the side chain, modified the activity. As a general trend, when chemical modifications of the basic structure produced a change in activity, the response was opposite in both insects used as biodetectors, indicating that a selective variation in the activity may be achieved by chemical modifications of the cucurbitacin skeleton.

  DOI：

  10.1021/jf4002457