(Z)-4-bromo-5-(bromomethylene)-3-(1'-bromoethyl)-2(5H)-furanone | 247167-53-9

• 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: (Z)-4-bromo-5-(bromomethylene)-3-(1'-bromoethyl)-2(5H)-furanone
• 英文别名: 4-Bromo-5-(bromomethylene)-3-(1-bromoethyl)-2(5H)-furanone；(5Z)-4-bromo-3-(1-bromoethyl)-5-(bromomethylidene)furan-2-one
• CAS: 247167-53-9
• 化学式: C₇H₅Br₃O₂
• 分子量: 360.827
• InChiKey: PJBLEHRNJNWSMS-RQOWECAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  (Z)-4-bromo-5-(bromomethylene)-3-ethyl-2(5H)-furanone 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 18.0h， 生成 (Z)-4-bromo-5-(bromomethylene)-3-(1'-bromoethyl)-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

• Production of furanones
  申请人：Unisearch Limited, A.C.N.

  公开号：US07064220B1

  公开（公告）日：2006-06-20

  The present invention relates to the side chain functionalization of fimbrolides (halogenated 3-alkyl-5-methylene-2(5H)-furanones) and their synthetic analogues, that yields fimbrolides substituted with a halogen, an oxygen or a nitrogen functionality in the alkyl chain, especially fimbrolide alcohols, carboxylate and sulfinate and sulfonate esters, ethers, aldehydes, ketones, acids, amides, nitro derivatives, hydrophobic, hydrophilic and fluorophilic alkyl derivatives and a polymers.

  本发明涉及对菌毛环内酯（卤代的3-烷基-5-亚甲基-2（5H）-呋喃酮）及其合成类似物的侧链官能化，得到用卤素、氧或氮官能团取代烷基链的菌毛环内酯，特别是菌毛环内酯醇、羧酸盐和磺酸盐酯、醚、醛、酮、酸、酰胺、硝基衍生物、亲水、疏水和亲氟烷基衍生物以及聚合物。
• Production of Furanones
  申请人：Read Roger

  公开号：US20080167373A1

  公开（公告）日：2008-07-10

  The present invention relates to the side chain functionalization of fimbrolides (halogenated 3 -alkyl- 5 -methylene- 2 ( 5 H)-furanones) and their synthetic analogues, that yields fimbrolides substituted with a halogen, an oxygen or a nitrogen functionality in the alkyl chain, especially fimbrolide alcohols, caboxylate and sulfinate and sulfonate esters, ethers, aldehydes, ketones, acids, amides, nitro derivatives, hydrophobic, hydrophilic and fluorophilic alkyl derivatives and polymers.

  本发明涉及纤毛菌素（卤代3-烷基-5-亚甲基-2（5H）-呋喃酮）及其合成类似物的侧链官能化，产生取代了卤素，氧或氮官能团的纤毛菌素，特别是纤毛菌素醇，羧酸酯，磺酸酯，醚，醛，酮，酸，酰胺，硝基衍生物，疏水，亲水和亲氟烷基衍生物和聚合物。
• 抗汚れ重合体組成物
  申请人：アクアカルチャー、シーアールシー、リミテッド

  公开号：JP2002508800A

  公开（公告）日：2002-03-19

  \n (57)【要約】\n抗汚れ性を有する押出成形可能な重合体であって、１以上の有機抗汚れ剤を含有し、かつ、天然の水性環境に実質的に浸漬させた場合に少なくとも１００日という長期間にわたって広範囲の抗汚れ活性を有する重合体。\n

  \(57)/(57)/(57)/(57)/(57)/(57)/(57)}[Summary] 一种具有防染色特性的可挤出聚合物，含有一种或多种有机防染色剂，在长时间（至少 100 天）浸泡在天然水环境中时具有广泛的防染色活性。\n
• ANTIFOULING POLYMERS
  申请人：Aquaculture CRC Limited

  公开号：EP0996681A1

  公开（公告）日：2000-05-03
• EP0996681A4
  申请人：——

  公开号：EP0996681A4

  公开（公告）日：2005-01-05