9,12,15-octadecatrien-6-ynoic acid methyl ester | 69287-41-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 9,12,15-octadecatrien-6-ynoic acid methyl ester
• 英文别名: Methyl-9,12,15-octadecatrien-6-ynoat；dicranin methyl ester；methyl (9Z,12Z,15Z)-octadeca-9,12,15-trien-6-ynoate
• CAS: 69287-41-8
• 化学式: C₁₉H₂₈O₂
• 分子量: 288.43
• InChiKey: FEGFXBKBZCJHCW-YSTUJMKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9,12,15-octadecatrien-6-ynoic acid methyl ester 在 N-溴代丁二酰亚胺(NBS) 、 水 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 13.0h， 以73%的产率得到(9Z,12Z)-methyl 14-(3-ethyloxiran-2-yl)tetradeca-9,12-dien-6-ynoate
  参考文献：
  名称：

  A Reactive Conjugated Allene Involved in the Biosynthesis of Volatile Oxylipins in the Moss Dicranum scoparium

  摘要：

  We addressed the role of the unusual acetylenic fatty acid dicranin as a precursor for volatile oxylipins in the moss Dicranum scoparium. Dicranin is transformed immediately after mechanical wounding of moss tissue to volatile C5- and C6-oxylipins. The transformation of synthetic deuterium labeled dicranin was monitored using LC/MS analysis and multivariate statistics to identify polar metabolites produced during volatile formation. Among the newly formed oxylipins is a highly reactive conjugated C13 allene with similar degrees of labeling compared to the C5 volatiles suggesting that it results as second cleavage product from the biosynthesis of pentenal and pentenone.

  DOI：

  10.1021/ol201114g

文献信息

• Novel Acetylenic Oxylipins from the Moss Dicranum scoparium with Antifeeding Activity against Herbivorous Slugs
  作者：Martin Rempt、Georg Pohnert

  DOI：10.1002/anie.201000825

  日期：2010.6.28

  A slug stopper: The defensive properties of oxylipins from the moss Dicranum scoparium are far more active than required to fend off herbivory by a common slug. The precursor‐guided structure elucidation of seven novel and several known unusual oxylipins was supported by chemometric data mining.

  塞子塞：来自苔藓龙骨草（Dicranum scoparium）的脂环素的防御特性远比通过普通塞子抵御草食动物所需的活性高得多。化学计量学数据挖掘支持了对七个新颖的和几种已知的不寻常的脂蛋白的前体导向结构的阐明。