13-oxo-epi-costuslactone | 1170682-21-9

• 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: 13-oxo-epi-costuslactone
• 英文别名: (3R,3aS,6aR,9aR,9bS)-6,9-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-3-carbaldehyde
• CAS: 1170682-21-9
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: PSPACFCJQGYFON-PEDHHIEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  2-bromo-4-methyl-2H-furan-5-one 、 13-oxo-epi-costuslactone 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 (3E,3aS,6aR,9aR,9bS)-6,9-dimethylidene-3-[[(2S)-4-methyl-5-oxo-2H-furan-2-yl]oxymethylidene]-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one 、 (3E,3aS,6aR,9aR,9bS)-6,9-dimethylidene-3-[[(2R)-4-methyl-5-oxo-2H-furan-2-yl]oxymethylidene]-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
  参考文献：
  名称：

  New Chemical Clues for Broomrape-Sunflower Host−Parasite Interactions: Synthesis of Guaianestrigolactones

  摘要：

  A comparative structure-activity relationship (SAR) study has been conducted with several guaianolide sesquiterpene lactones (SLs) as inducers of the germination of sunflower broomrape (Orobanche cumana) seeds. Compounds were selected and synthesized to study the influence of the lactone-enol-gamma-lactone moiety on the selectivity of SLs toward the stimulation of sunflower broomrape germination. The results clearly illustrate that SLs are recognized only by O. cumana, while the introduction of a strigol-like second lactone moiety in the guaianolide backbone results in the loss of specificity and hence the germination of other broomrape species. We have named this new class of compounds guaianestrigolactones (GELs).

  DOI：

  10.1021/jf900870j
• 作为产物：
  描述：

  11α-hydroxymethyldehydrocostuslactone 在 戴斯-马丁氧化剂 作用下， 以57%的产率得到13-oxo-epi-costuslactone
  参考文献：
  名称：

  New Chemical Clues for Broomrape-Sunflower Host−Parasite Interactions: Synthesis of Guaianestrigolactones

  摘要：

  A comparative structure-activity relationship (SAR) study has been conducted with several guaianolide sesquiterpene lactones (SLs) as inducers of the germination of sunflower broomrape (Orobanche cumana) seeds. Compounds were selected and synthesized to study the influence of the lactone-enol-gamma-lactone moiety on the selectivity of SLs toward the stimulation of sunflower broomrape germination. The results clearly illustrate that SLs are recognized only by O. cumana, while the introduction of a strigol-like second lactone moiety in the guaianolide backbone results in the loss of specificity and hence the germination of other broomrape species. We have named this new class of compounds guaianestrigolactones (GELs).

  DOI：

  10.1021/jf900870j

文献信息

• New Chemical Clues for Broomrape-Sunflower Host−Parasite Interactions: Synthesis of Guaianestrigolactones
  作者：Francisco A. Macías、María D. García-Díaz、Alejandro Pérez-de-Luque、Diego Rubiales、Juan C. G. Galindo

  DOI：10.1021/jf900870j

  日期：2009.7.8

  A comparative structure-activity relationship (SAR) study has been conducted with several guaianolide sesquiterpene lactones (SLs) as inducers of the germination of sunflower broomrape (Orobanche cumana) seeds. Compounds were selected and synthesized to study the influence of the lactone-enol-gamma-lactone moiety on the selectivity of SLs toward the stimulation of sunflower broomrape germination. The results clearly illustrate that SLs are recognized only by O. cumana, while the introduction of a strigol-like second lactone moiety in the guaianolide backbone results in the loss of specificity and hence the germination of other broomrape species. We have named this new class of compounds guaianestrigolactones (GELs).