melampomagnolide A | 93930-16-6

• 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: melampomagnolide A
• 英文别名: (1S,4R,6R,9E,11R)-4-(hydroxymethyl)-9-methyl-14-methylidene-5,12-dioxatricyclo[9.3.0.04,6]tetradec-9-en-13-one
• CAS: 93930-16-6
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: KDQGMEXTUQAXLS-ZMRUPOPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  melampomagnolide A 在 叔丁基过氧化氢 、 selenium(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 以3%的产率得到14,15-dihydroxy-1β,10β-epoxide-cis,cis-germacranolide
  参考文献：
  名称：

  Synthesis of melampolides and cis,cis-germacranolides as natural herbicide models

  摘要：

  The comparative study between the theoretical molecular properties of the starting materials and the yields in the transformation of melampolides to cis,cis-germacranolides using SeO2/t-BuOOH (TBHP) as oxidant allows to establish a feasible relationship with their values of dipolar moment. Conditions for this transformation are optimized and some mechanistic considerations are made based in this finding. Cluster analysis of the phytotoxic activity of the melampolides and cis, cis-germacranolides obtained shows that the activity is greatly influenced by the spatial shape of the backbone, prevailing upon other factors such as the presence of reactive functional groups. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.128
• 作为产物：
  描述：

  木香烃内酯 在 叔丁基过氧化氢 、 selenium(IV) oxide 、 sodium acetate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 melampomagnolide A
  参考文献：
  名称：

  Synthesis of melampolides and cis,cis-germacranolides as natural herbicide models

  摘要：

  The comparative study between the theoretical molecular properties of the starting materials and the yields in the transformation of melampolides to cis,cis-germacranolides using SeO2/t-BuOOH (TBHP) as oxidant allows to establish a feasible relationship with their values of dipolar moment. Conditions for this transformation are optimized and some mechanistic considerations are made based in this finding. Cluster analysis of the phytotoxic activity of the melampolides and cis, cis-germacranolides obtained shows that the activity is greatly influenced by the spatial shape of the backbone, prevailing upon other factors such as the presence of reactive functional groups. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.128

文献信息

• Potential allelopathic activity of several sesquiterpene lactone models
  作者：Francisco A. Macías、Juan Carlos G. Galindo、Guillermo M. Massanet

  DOI：10.1016/0031-9422(92)80343-d

  日期：1992.6

  and synthetic sesquiterpene lactones with eudesmanolide, melampolide, cis,cis -germacranolide, and guaianolide skeletons have been prepared and tested as allelochemicals. The effect of a series of aqueous solutions at 10 −4 -10 −9 M ofthis collection is evaluated. The specific structural requirements related to their activity is discussed. The natural sesquiterpene lactones soulangianolide A, melampomagnolide

  摘要 已制备并测试了 12 种天然和合成倍半萜内酯的集合，这些内酯具有 eudesmanolide、melampolide、cis、cis-germacranolide 和 guaianolide 骨架。评估了该集合的10 -4 -10 -9 M 处的一系列水溶液的效果。讨论了与其活动相关的具体结构要求。已使用SeO 2 和叔丁基过氧化氢从木香内酯、小白菊内酯和脱氢木香内酯合成天然倍半萜内酯soulangianolide A、melampomagnolide A和B、zaluzanin C和isozaluzanin C。合成化合物的结构通过核磁共振光谱确定。
• Melampolides from Magnolia grandiflora
  作者：Farouk S. El-Feraly

  DOI：10.1016/s0031-9422(00)80557-9

  日期：1984.1

  Abstract Two isomeric melampolides, melampomagnolide A and melampomagnolide B, were isolated from the newly formed leaves of Magnolia grandiflora . Their stereochemical structures were established by spectroscopic means, and by chemical correlation with soulangianolide A and parthenolide, respectively.

  摘要 从广玉兰新形成的叶片中分离得到两种异构体melampolides，melampomagnolide A和melampomagnolide B。它们的立体化学结构是通过光谱方法建立的，并分别通过与 Soulangianolide A 和小白菊内酯的化学相关性建立。
• Synthesis of melampolides and cis,cis-germacranolides as natural herbicide models
  作者：Francisco A. Macías、Raúl F. Velasco、José A. Álvarez、Diego Castellano、Juan C.G. Galindo

  DOI：10.1016/j.tet.2004.06.128

  日期：2004.9

  The comparative study between the theoretical molecular properties of the starting materials and the yields in the transformation of melampolides to cis,cis-germacranolides using SeO2/t-BuOOH (TBHP) as oxidant allows to establish a feasible relationship with their values of dipolar moment. Conditions for this transformation are optimized and some mechanistic considerations are made based in this finding. Cluster analysis of the phytotoxic activity of the melampolides and cis, cis-germacranolides obtained shows that the activity is greatly influenced by the spatial shape of the backbone, prevailing upon other factors such as the presence of reactive functional groups. (C) 2004 Elsevier Ltd. All rights reserved.