(Z)-4-bromo-5-(bromomethylene)-3-hexyl-2(5H)-furanone | 183792-79-2

• 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-hexyl-2(5H)-furanone
• 英文别名: (5Z)-4-bromo-5-(bromomethylidene)-3-hexylfuran-2-one
• CAS: 183792-79-2
• 化学式: C₁₁H₁₄Br₂O₂
• 分子量: 338.039
• InChiKey: FLVMUOPUHKLSSG-CLFYSBASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  15
• 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

• 作为反应物：
  描述：

  (Z)-4-bromo-5-(bromomethylene)-3-hexyl-2(5H)-furanone 在 对甲苯磺酸 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 5.0h， 生成 (5Z)-4-bromo-5-(bromomethylidene)-3-hexyl-1-phenylpyrrol-2-one
  参考文献：
  名称：

  An efficient lactamization of fimbrolides to novel 1,5-dihydropyrrol-2-ones

  摘要：

  A new versatile method for the conversion of fimbrolides to the corresponding novel dihydropyrrol-2-ones is described. This new efficient lactamization protocol has the advantage of higher yields and can be used for the synthesis of a series of new dihydropyrrol-2-ones with interesting anti-bacterial properties. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.01.165
• 作为产物：
  描述：

  Ethyl-β-carethoxy-α-hexyl-levulinat 在 sodium hydroxide 、 硫酸 、 氢溴酸 、 溴 、 溶剂黄146 作用下， 以 水 、 甲苯 为溶剂， 反应 9.33h， 生成 (Z)-4-bromo-5-(bromomethylene)-3-hexyl-2(5H)-furanone
  参考文献：
  名称：

  硫酸催化的溴化2-烷基乙酰丙酸环化成3-烷基-5-亚甲基-2（5 H）-呋喃酮的再研究

  摘要：

  描述了由烷基取代的乙酰丙酸衍生物通过溴化和酸促进的内酯化合成乙基，丁基，己基和十二烷基取代的溴化物。使用乙酰丙酸作为模型，研究了潜在的反应，并讨论了改变溴化条件和改变酸浓度对产物分布的影响。二溴化在CHCl 3中进行得最好，在无EtOH的CHCl 3中进行，而不会形成酯。在98–100％H 2 SO 4中伴随氧化发生环化反应，但在100％H 2 SO 4中产生环戊内酯的产率最高。还描述了相关的贝克雷利物质的形成。

  DOI：

  10.1016/s0040-4020(97)10034-5

文献信息

• Furanone derivatives and methods of making same
  申请人：Kumar Naresh

  公开号：US20050215772A1

  公开（公告）日：2005-09-29

  Novel synthesis methods, to the products of such novel methods, and to uses of these products. In particular, the present invention provides methods for the reactions of furanones, in particular fimbrolides, with amines. The invention has particular application in the synthesis of halogenated 1,5-dihydro-pyrrol-2-one, 5-halomethylene substituted 1,5-dihydropyrrol-2-ones (lactam analogues of fimbriolides), 5-amino substituted furanones and 5-aminomethylene-2(5H)-furanones and their synthetic analogues. The invention also relates to novel compounds and uses thereof.

  本发明涉及新型合成方法、这些新型方法的产物及其用途。具体而言，本发明提供了一种将呋喃酮，特别是纤毛菌素与胺反应的方法。本发明在合成卤代1,5-二氢吡咯-2-酮、5-卤代亚甲基取代的1,5-二氢吡咯-2-酮（纤毛菌素的内酰胺类似物）、5-氨基取代的呋喃酮和5-氨基亚甲基-2（5H）-呋喃酮及其合成类似物方面具有特殊的应用。本发明还涉及新的化合物及其用途。
• 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.
• Reinvestigation of the sulfuric acid-catalysed cyclisation of brominated 2-alkyllevulinic acids to 3-alkyl-5-methylene-2(5H)-furanones
  作者：Anthony J. Manny、Staffan Kjelleberg、Naresh Kumar、Rocky de Nys、Roger W. Read、Peter Steinberg

  DOI：10.1016/s0040-4020(97)10034-5

  日期：1997.11

  through bromination and acid promoted lactonisation is described. The underlying reactions have been investigated using levulinic acid as a model, and the effects of varying the bromination conditions and changing acid concentration on product distribution are discussed. Dibromination proceeds best in CHCl3 and proceeds in EtOH-free CHCl3 without the complication of ester formation. Cyclisation occurs

  描述了由烷基取代的乙酰丙酸衍生物通过溴化和酸促进的内酯化合成乙基，丁基，己基和十二烷基取代的溴化物。使用乙酰丙酸作为模型，研究了潜在的反应，并讨论了改变溴化条件和改变酸浓度对产物分布的影响。二溴化在CHCl 3中进行得最好，在无EtOH的CHCl 3中进行，而不会形成酯。在98–100％H 2 SO 4中伴随氧化发生环化反应，但在100％H 2 SO 4中产生环戊内酯的产率最高。还描述了相关的贝克雷利物质的形成。
• An efficient lactamization of fimbrolides to novel 1,5-dihydropyrrol-2-ones
  作者：Wai Kean Goh、George Iskander、David StC Black、Naresh Kumar

  DOI：10.1016/j.tetlet.2007.01.165

  日期：2007.3

  A new versatile method for the conversion of fimbrolides to the corresponding novel dihydropyrrol-2-ones is described. This new efficient lactamization protocol has the advantage of higher yields and can be used for the synthesis of a series of new dihydropyrrol-2-ones with interesting anti-bacterial properties. (c) 2007 Elsevier Ltd. All rights reserved.