C56 | 199744-38-2

• 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: C56
• 英文别名: 5-(bromomethylene)-2(5H)-furanone；5-(bromomethylene)furan-2(5H)-one；5-(Bromomethylidene)furan-2(5H)-one；5-(bromomethylidene)furan-2-one
• CAS: 199744-38-2
• 化学式: C₅H₃BrO₂
• 分子量: 174.982
• InChiKey: LKFZLSZOWSMZDX-UHFFFAOYSA-N

物化性质

• 熔点：
  82-86°C
• 沸点：
  233.4±33.0 °C(Predicted)
• 密度：
  2.097±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  2-噻吩硼酸 、 C56 在 bis-triphenylphosphine-palladium(II) chloride 、 四丁基碘化铵 、 cesium fluoride 作用下， 以 水 、 甲苯 为溶剂， 反应 36.0h， 以62%的产率得到4--buten-(2)-olid (1.4)
  参考文献：
  名称：

  Suzuki-Miyaura反应合成新的芳基取代的呋喃-2（5 H）-一

  摘要：

  一系列新的5-芳基呋喃-2（5 H）-和5-芳基-4-芳基呋喃-2（5 H）-是通过氟溴化物衍生物5-（溴代亚甲基）呋喃-2的Suzuki-Miyaura反应合成的。 （5 H）-1和4-溴-5-（溴亚甲基）呋喃-2（5 H）-1 。在4-溴-5-（溴亚甲基）呋喃-2（5 H）-上的区域选择性Suzuki-Miyaura反应可以合成不对称取代的5-亚芳基-4-芳基呋喃-2（5 H）-。中间体5-亚芳基-4-溴呋喃-2（5 H）-one的晶体结构揭示了有趣的Br⋯O卤素键。

  DOI：

  10.1016/j.tet.2011.02.014
• 作为产物：
  描述：

  3-bromolevulinic acid 、 5-bromolaevulinic acid 在 硫酸 作用下， 生成 furanone 30 、 5-(dibromomethylene)-2(5H)-furanone 、 C56
  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
• 作为试剂：
  描述：

  、 (Z)-4-bromo-5-(bromomethylene)-3-butylfuran-2(5H)-one 、 3-butyl-5-(dibromomethylene)-2(5H)-furanone 在 (Z)-4-bromo-5-(bromomethylene)-3-butylfuran-2(5H)-one 、 3-butyl-5-(dibromomethylene)-2(5H)-furanone 、 C56 、 furanone 30 、 5-(dibromomethylene)-2(5H)-furanone 作用下， 生成 5-(dibromomethylene)-2(5H)-furanone
  参考文献：
  名称：

  B. Anthracis Prevention and Treatment: Mutant B. Anthracis Lacking Luxs Activity and Furanone Inhibition of Growth, AI-2 Quorum Sensing, and Toxin Production

  摘要：

  本发明涉及到的发现是，炭疽杆菌具有编码功能性LuxS多肽的luxS基因，并且炭疽杆菌合成功能性的AI-2群体感应分子。本发明提供了缺乏luxS基因功能、不产生功能性AI-2分子并且与野生型炭疽杆菌相比具有生长缺陷的突变炭疽杆菌细菌。本发明还涉及通过抑制炭疽杆菌LuxS多肽的活性或暴露于呋喃酮来抑制炭疽杆菌的生长，或预防或治疗炭疽杆菌感染的方法。特别地，本发明涉及使用呋喃酮这种抑制AI-2介导的群体感应的化合物来抑制炭疽杆菌的生长，抑制炭疽杆菌毒素的产生，特别是保护性抗原的产生，并预防或治疗炭疽杆菌感染。本发明还提供了通过给予含有luxS基因突变的炭疽杆菌细胞的疫苗来预防炭疽杆菌感染或增强对炭疽杆菌感染的免疫反应的方法。

  公开号：

  US20120157522A1

文献信息

• Furanone compounds and lactam analogues thereof
  申请人：Kumar Naresh

  公开号：US20100035948A1

  公开（公告）日：2010-02-11

  The present invention provides a compound of formula I and a compound of formula II, methods of use and formulations thereof.

  本发明提供了一种I式化合物和一种II式化合物，以及其使用方法和配方。
• Synthesis of new aryl substituted furan-2(5H)-ones using the Suzuki–Miyaura reaction
  作者：Ruonan Zhang、George Iskander、Paulo da Silva、Daniel Chan、Valentina Vignevich、Vi Nguyen、Mohan M. Bhadbhade、David StC Black、Naresh Kumar

  DOI：10.1016/j.tet.2011.02.014

  日期：2011.4

  5-arylidenefuran-2(5H)-ones and 5-arylidene-4-arylfuran-2(5H)-ones were synthesized via the Suzuki–Miyaura reactions of fimbrolide derivatives 5-(bromomethylene)furan-2(5H)-one and 4-bromo-5-(bromomethylene)furan-2(5H)-one, respectively. A regioselective Suzuki–Miyaura reaction on 4-bromo-5-(bromomethylene)furan-2(5H)-one allowed the synthesis of unsymmetrically substituted 5-arylidene-4-arylfuran-2(5H)-ones. The

  一系列新的5-芳基呋喃-2（5 H）-和5-芳基-4-芳基呋喃-2（5 H）-是通过氟溴化物衍生物5-（溴代亚甲基）呋喃-2的Suzuki-Miyaura反应合成的。 （5 H）-1和4-溴-5-（溴亚甲基）呋喃-2（5 H）-1 。在4-溴-5-（溴亚甲基）呋喃-2（5 H）-上的区域选择性Suzuki-Miyaura反应可以合成不对称取代的5-亚芳基-4-芳基呋喃-2（5 H）-。中间体5-亚芳基-4-溴呋喃-2（5 H）-one的晶体结构揭示了有趣的Br⋯O卤素键。
• 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.