(2'R,4a'R,5'R,6'R,7'S,8'R,8a'R,9'R)-7',8'-dimethyl-9'-(((E)-2-methylbut-2-enoyl)oxy)-8'-(2-((S)-2-oxotetrahydrofuran-3-yl)ethyl)octahydrospiro[oxirane-2,4'-[2,4a](epoxymethano)naphthalene]-5',6'-diyl diacetate | 148935-77-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2'R,4a'R,5'R,6'R,7'S,8'R,8a'R,9'R)-7',8'-dimethyl-9'-(((E)-2-methylbut-2-enoyl)oxy)-8'-(2-((S)-2-oxotetrahydrofuran-3-yl)ethyl)octahydrospiro[oxirane-2,4'-[2,4a](epoxymethano)naphthalene]-5',6'-diyl diacetate
• CAS: 148935-77-7
• 化学式: C₂₉H₄₀O₁₀
• 分子量: 548.631
• InChiKey: GDUGBAUQYSVWBF-SVCSIPHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  39.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  126.96
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2'R,4a'R,5'R,6'R,7'S,8'R,8a'R,9'R)-7',8'-dimethyl-9'-(((E)-2-methylbut-2-enoyl)oxy)-8'-(2-((S)-2-oxotetrahydrofuran-3-yl)ethyl)octahydrospiro[oxirane-2,4'-[2,4a](epoxymethano)naphthalene]-5',6'-diyl diacetate 在 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以50 mg的产率得到[(1R,2R,3R,4S,5R,6R,8R,10S,11R)-2-acetyloxy-10-hydroxy-4,5-dimethyl-5-[2-[(3S)-2-oxooxolan-3-yl]ethyl]spiro[9-oxatricyclo[6.2.2.01,6]dodecane-11,2'-oxirane]-3-yl] acetate
  参考文献：
  名称：

  Neo-clerodane insect antifeedants from Scutellaria galericulata

  摘要：

  Two new neo-clerodane diterpenoids, scutegalins A and B, have been isolated from the acetone extract of the aerial parts of Scutellaria galericulata, in addition to the known diterpenes jodrellin T and 14,15-dihydrojodrellin T. The structures of the new diterpenoids were established by chemical and spectroscopic means, including an X-ray diffraction analysis of a derivative of scutegalin B. The antifeedant activity of scutegalins A and B and derivatives against Spodoptera littoralis has been determined and structure-antifeedant activity relationships are discussed.

  DOI：

  10.1016/0031-9422(93)85509-p
• 作为产物：
  描述：

  7-O-acetylscutegalin B 在 chromium trioxide-pyridine complex 作用下， 反应 24.0h， 以350 mg的产率得到(2'R,4a'R,5'R,6'R,7'S,8'R,8a'R,9'R)-7',8'-dimethyl-9'-(((E)-2-methylbut-2-enoyl)oxy)-8'-(2-((S)-2-oxotetrahydrofuran-3-yl)ethyl)octahydrospiro[oxirane-2,4'-[2,4a](epoxymethano)naphthalene]-5',6'-diyl diacetate
  参考文献：
  名称：

  Neo-clerodane insect antifeedants from Scutellaria galericulata

  摘要：

  Two new neo-clerodane diterpenoids, scutegalins A and B, have been isolated from the acetone extract of the aerial parts of Scutellaria galericulata, in addition to the known diterpenes jodrellin T and 14,15-dihydrojodrellin T. The structures of the new diterpenoids were established by chemical and spectroscopic means, including an X-ray diffraction analysis of a derivative of scutegalin B. The antifeedant activity of scutegalins A and B and derivatives against Spodoptera littoralis has been determined and structure-antifeedant activity relationships are discussed.

  DOI：

  10.1016/0031-9422(93)85509-p

文献信息

• From a Phagostimulant Natural Product to Semisynthetic Antifeedants Against <i>Spodoptera </i><i>l</i><i>ittoralis</i> Larvae:  Chemical Transformations of the Neoclerodane Diterpenoid Scutegalin B
  作者：Beatriz Rodríguez、Benjamín Rodríguez、María C. de la Torre、Monique S. J. Simmonds、Wally M. Blaney

  DOI：10.1021/np9805286

  日期：1999.4.1

  Scutegalin B (4), a natural neoclerodane diterpenoid possessing phagostimulant activity against larvae of the lepidopteran Spodoptera littoralis, has been subjected to a series of chemical transformations obtaining several derivatives. The activity of some of these changes to antifeedant (10, 12, 16, and 17), although other derivatives are inactive (6, 7, and 15) or maintain phagostimulant activity

  Scutegalin B（4）是一种天然新环戊烷二萜类化合物，具有对鳞翅目斜纹夜蛾幼虫的诱食活性，已进行了一系列化学转化，获得了几种衍生物。尽管其他衍生物没有活性（6、7和15）或维持原料（4）的吞噬刺激活性（8和9），但其中一些改变对拒食剂的活性（10、12、16和17）。最有效的拒食剂是16，它具有16,15-内酯和（19S）-19，2α-半缩醛基团，而不是16,15-内酯和（19R）-（19-O-tigloyl）19,2α-吞噬刺激剂前体4的半缩醛。讨论了这些和其他结构活性关系，从而确定了生物作用受到最小结构变异的强烈调节。