(5E)-3-(4-bromobenzyl)-5-(2,4,6-trimethoxybenzylidene)-5H-furan-2-one | 959407-15-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (5E)-3-(4-bromobenzyl)-5-(2,4,6-trimethoxybenzylidene)-5H-furan-2-one
• 英文别名: (5E)-3-[(4-bromophenyl)methyl]-5-[(2,4,6-trimethoxyphenyl)methylidene]furan-2-one
• CAS: 959407-15-9
• 化学式: C₂₁H₁₉BrO₅
• 分子量: 431.283
• InChiKey: VDXRSHGRWWIPPC-LICLKQGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-(4-bromobenzyl)-furan-2(5H)-one 、 2,4,6-三甲氧基苯甲醛 在 叔丁基二甲硅基三氟甲磺酸酯 、 N,N-二异丙基乙胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以39%的产率得到(5E)-3-(4-bromobenzyl)-5-(2,4,6-trimethoxybenzylidene)-5H-furan-2-one
  参考文献：
  名称：

  Synthesis of 3-(4-Bromobenzyl)-5-(aryl methylene)-5H-furan-2-ones and Their Activity as Inhibitors of the Photosynthetic Electron Transport Chain

  摘要：

  A series of 12 3-(4-bromobenzyl)-5-(arylmethylene)-5H-furan-2-one lactones, designed using the naturally occurring toxin nostoclides as a lead structure, were synthesized and screened as potential inhibitors of photosynthetic electron transport. The structures were confirmed by H-1 and C-13 NMR, MS, and IR analyses. Their biological activity was evaluated both in vitro, as the ability to interfere with light-driven reduction of ferricyanide by isolated spinach chloroplast-s, and in vivo, as the capability to inhibite the oxygen production by intact Chlorella cells. Some of the compounds exhibited inhibitory properties in the micromolar range against basal and phosphorylating electron flow from water to K-3[Fe(CN)(6)], with no effect on uncoupled electron flow. Thus, they seem to behave as energy-transfer inhibitors. Although poor solubility in water may limit their effectiveness, the active derivatives could present structures to be exploited for the design of new substances endowed with herbicidal activity.

  DOI：

  10.1021/jf072120x

文献信息

• Synthesis of 3-(4-Bromobenzyl)-5-(aryl methylene)-5<i>H</i>-furan-2-ones and Their Activity as Inhibitors of the Photosynthetic Electron Transport Chain
  作者：Luiz C. A. Barbosa、Marcelo E. Rocha、Róbson R. Teixeira、Célia R.A. Maltha、Giuseppe Forlani

  DOI：10.1021/jf072120x

  日期：2007.10.1

  A series of 12 3-(4-bromobenzyl)-5-(arylmethylene)-5H-furan-2-one lactones, designed using the naturally occurring toxin nostoclides as a lead structure, were synthesized and screened as potential inhibitors of photosynthetic electron transport. The structures were confirmed by H-1 and C-13 NMR, MS, and IR analyses. Their biological activity was evaluated both in vitro, as the ability to interfere with light-driven reduction of ferricyanide by isolated spinach chloroplast-s, and in vivo, as the capability to inhibite the oxygen production by intact Chlorella cells. Some of the compounds exhibited inhibitory properties in the micromolar range against basal and phosphorylating electron flow from water to K-3[Fe(CN)(6)], with no effect on uncoupled electron flow. Thus, they seem to behave as energy-transfer inhibitors. Although poor solubility in water may limit their effectiveness, the active derivatives could present structures to be exploited for the design of new substances endowed with herbicidal activity.