methyl 4'-benzyloxy-2'-(3-methylbut-2-enyloxy)cinnamate | 107052-29-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl 4'-benzyloxy-2'-(3-methylbut-2-enyloxy)cinnamate
• 英文别名: Methyl (2E)-3-{4-(benzyloxy)-2-[(3-methylbut-2-en-1-yl)oxy]phenyl}prop-2-enoate；methyl (E)-3-[2-(3-methylbut-2-enoxy)-4-phenylmethoxyphenyl]prop-2-enoate
• CAS: 107052-29-9
• 化学式: C₂₂H₂₄O₄
• 分子量: 352.43
• InChiKey: DLXYMMRFBAVOAS-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4'-benzyloxy-2'-(3-methylbut-2-enyloxy)cinnamate 在 N,N-二乙基苯胺 作用下， 反应 4.0h， 以71%的产率得到7-benzyloxy-6-prenylcoumarin
  参考文献：
  名称：

  Biological Activity of Marmesin and Demethylsuberosin against a Generalist Herbivore, Spodoptera exigua (Lepidoptera:  Noctuidae)

  摘要：

  No significant effects were observed in bioassays designed to measure impact of the furanocoumarin precursors demethylsuberosin and marmesin on typical physiological parameters (survival and development rate) of the generalist herbivore, Spodoptera exigua (Hubner). The linear furanocoumarin psoralen did increase developmental times and reduce survival. All of these compounds were demonstrated to have significant behavioral (feeding deterrence) effects against both first and third instars of S. exigua in diet-incorporation bioassays. In tests initiated with first instars, significantly (P < 0.05) more larvae preferred control diet to diet containing marmesin or psoralen on all five sample dates; control diets were significantly preferred to diets with demethylsuberosin on three of five sample dates. Similar results were observed for tests initiated with third instar larvae, but the avoidance of demethylsuberosin-containing diets was stronger. Therefore, assaying furanocoumarin precursors just for effects on growth and survival may not provide an accurate picture of the ecological importance of these compounds.

  DOI：

  10.1021/jf960156b
• 作为产物：
  描述：

  7-(benzyloxy)-2H-chromen-2-one 在 sodium methylate 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 methyl 4'-benzyloxy-2'-(3-methylbut-2-enyloxy)cinnamate
  参考文献：
  名称：

  通过香豆酸酯衍生物的对位-克莱森重排合成线性香豆素：全脂蛋白，去甲基亚脂蛋白和ostruthin的全合成

  摘要：

  加热4'- O-苄基香豆酸酯（3）的2'- O-烯丙基化衍生物（3），直接通过连续的对-克莱森重排和再内酯化作用提供相应的线性烯丙基化伞形酮（1）。

  DOI：

  10.1039/c39860001264

文献信息

• Synthesis of linear coumarins via para-Claisen rearrangement of coumarate ester derivatives: total synthesis of suberosin, demethylsuberosin, and ostruthin
  作者：Nicholas Cairns、Laurence M. Harwood、David P. Astles

  DOI：10.1039/c39860001264

  日期：——

  Heating 2′-O-prenylated derivatives of 4′-O-benzyl methyl coumarates (3) furnishes the corresponding linear prenylated umbelliferones (1) directly via sequential para-Claisen rearrangement and relactonisation.

  加热4'- O-苄基香豆酸酯（3）的2'- O-烯丙基化衍生物（3），直接通过连续的对-克莱森重排和再内酯化作用提供相应的线性烯丙基化伞形酮（1）。
• Cairns, Nicholas; Harwood, Laurence M.; Astles, David P., Journal of the Chemical Society. Perkin transactions I, 1994, # 21, p. 3101 - 3108
  作者：Cairns, Nicholas、Harwood, Laurence M.、Astles, David P.

  DOI：——

  日期：——
• Biological Activity of Marmesin and Demethylsuberosin against a Generalist Herbivore, <i>Spodoptera exigua </i>(Lepidoptera:  Noctuidae)
  作者：John T. Trumble、Jocelyn G. Millar

  DOI：10.1021/jf960156b

  日期：1996.1.1

  No significant effects were observed in bioassays designed to measure impact of the furanocoumarin precursors demethylsuberosin and marmesin on typical physiological parameters (survival and development rate) of the generalist herbivore, Spodoptera exigua (Hubner). The linear furanocoumarin psoralen did increase developmental times and reduce survival. All of these compounds were demonstrated to have significant behavioral (feeding deterrence) effects against both first and third instars of S. exigua in diet-incorporation bioassays. In tests initiated with first instars, significantly (P < 0.05) more larvae preferred control diet to diet containing marmesin or psoralen on all five sample dates; control diets were significantly preferred to diets with demethylsuberosin on three of five sample dates. Similar results were observed for tests initiated with third instar larvae, but the avoidance of demethylsuberosin-containing diets was stronger. Therefore, assaying furanocoumarin precursors just for effects on growth and survival may not provide an accurate picture of the ecological importance of these compounds.