3-hexyl-4-bromo-5-methylene-2(5H)-furanone | 1245286-58-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 3-hexyl-4-bromo-5-methylene-2(5H)-furanone
• 英文别名: 4-Bromo-3-hexyl-5-methylidenefuran-2-one
• CAS: 1245286-58-1
• 化学式: C₁₁H₁₅BrO₂
• 分子量: 259.143
• InChiKey: AVZPXKJOALWIJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-hexyl-5-hydroxy-5-methyl-2(5H)-furanone 在 溴 、 吡啶 作用下， 以 氯仿 为溶剂， 反应 1.83h， 以24%的产率得到3-hexyl-4-bromo-5-methylene-2(5H)-furanone
  参考文献：
  名称：

  Structure–activity relationship of brominated 3-alkyl-5-methylene-2(5H)-furanones and alkylmaleic anhydrides as inhibitors of Salmonella biofilm formation and quorum sensing regulated bioluminescence in Vibrio harveyi

  摘要：

  A library of 25 10-unsubstituted and 10-bromo or 10-acetoxy 3-alkyl-5-methylene-2(5H)-furanones and two 3-alkylmaleic anhydrides was synthesized using existing and new methods. This library was tested for the antagonistic effect against the biofilm formation by Salmonella Typhimurium and the quorum sensing regulated bioluminescence of Vibrio harveyi. The length of the 3-alkyl chain and the bromination pattern of the ring structure were found to have a major effect on the biological activity of the 10-unsubstituted furanones. Remarkably, the introduction of a bromine atom on the 10 position of the 3-alkyl chain did drastically enhance the activity of the furanones in both biological test systems. The introduction of an acetoxy function in this position did in general not improve the activity. Finally, the potential of the (bromo) alkylmaleic anhydrides as a new and chemically easily accessible class of biofilm and quorum sensing inhibitors was demonstrated. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.055

文献信息

• Structure–activity relationship of brominated 3-alkyl-5-methylene-2(5H)-furanones and alkylmaleic anhydrides as inhibitors of Salmonella biofilm formation and quorum sensing regulated bioluminescence in Vibrio harveyi
  作者：Hans P. Steenackers、Jeremy Levin、Joost C. Janssens、Ami De Weerdt、Jan Balzarini、Jos Vanderleyden、Dirk E. De Vos、Sigrid C. De Keersmaecker

  DOI：10.1016/j.bmc.2010.05.055

  日期：2010.7

  A library of 25 10-unsubstituted and 10-bromo or 10-acetoxy 3-alkyl-5-methylene-2(5H)-furanones and two 3-alkylmaleic anhydrides was synthesized using existing and new methods. This library was tested for the antagonistic effect against the biofilm formation by Salmonella Typhimurium and the quorum sensing regulated bioluminescence of Vibrio harveyi. The length of the 3-alkyl chain and the bromination pattern of the ring structure were found to have a major effect on the biological activity of the 10-unsubstituted furanones. Remarkably, the introduction of a bromine atom on the 10 position of the 3-alkyl chain did drastically enhance the activity of the furanones in both biological test systems. The introduction of an acetoxy function in this position did in general not improve the activity. Finally, the potential of the (bromo) alkylmaleic anhydrides as a new and chemically easily accessible class of biofilm and quorum sensing inhibitors was demonstrated. (C) 2010 Elsevier Ltd. All rights reserved.