5-(dibromomethylene)-3-methylfuran-2(5H)-one | 361145-60-0

• 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: 5-(dibromomethylene)-3-methylfuran-2(5H)-one
• 英文别名: 5-(dibromomethylene)-3-methylfuran-2-one；5-(Dibromomethylene)-3-methyl-furan-2-one；5-(dibromomethylidene)-3-methylfuran-2-one
• CAS: 361145-60-0
• 化学式: C₆H₄Br₂O₂
• 分子量: 267.905
• InChiKey: FOBOIEIIDMDQPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  5-(dibromomethylene)-3-methylfuran-2(5H)-one 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 12.0h， 以50%的产率得到3-(bromomethyl)-5-(dibromomethylene)furan-2(5H)-one
  参考文献：
  名称：

  确定溴化呋喃酮抑制大肠杆菌生物膜形成的重要结构元素。

  摘要：

  合成了结构上密切相关的呋喃酮的集合，以鉴定溴化呋喃酮中抑制细菌生物膜形成的最重要的结构元素。结果表明，呋喃酮环上的共轭环外乙烯基溴化物是最重要的无毒但对大肠杆菌生物膜形成具有抑制活性的结构元素。发现在饱和碳上带有单取代溴化物基团的呋喃酮具有减弱细菌生长的毒性作用。

  DOI：

  10.1016/j.bmcl.2007.12.032
• 作为产物：
  描述：

  Alpha-甲基乙酰丙酸 在 溴 、 溶剂黄146 、 硫酸 作用下， 反应 1.33h， 以13%的产率得到(Z)-4-bromo-5-(bromomethylene)-3-methylfuran-2(5H)-one
  参考文献：
  名称：

  确定溴化呋喃酮抑制大肠杆菌生物膜形成的重要结构元素。

  摘要：

  合成了结构上密切相关的呋喃酮的集合，以鉴定溴化呋喃酮中抑制细菌生物膜形成的最重要的结构元素。结果表明，呋喃酮环上的共轭环外乙烯基溴化物是最重要的无毒但对大肠杆菌生物膜形成具有抑制活性的结构元素。发现在饱和碳上带有单取代溴化物基团的呋喃酮具有减弱细菌生长的毒性作用。

  DOI：

  10.1016/j.bmcl.2007.12.032

文献信息

• NON-AMPHIPHILE-BASED WATER-IN-WATER EMULSION AND USES THEREOF
  申请人：LUK Yan-Yeung

  公开号：US20090269323A1

  公开（公告）日：2009-10-29

  The present invention relates to a non-amphiphile-based water-in-water emulsion composition. The non-amphiphile-based water-in-water emulsion composition includes a water-soluble polymer, a non-amphiphilic lyotropic mesogen encapsulated by the water-soluble polymer; and water. In one embodiment, the non-amphiphilic lyotropic mesogen includes, without limitation, a lyotropic chromonic liquid crystal, and more specifically disodium cromoglycate (DSCG). In another embodiment, the water-soluble polymer can include, without limitation, a polyacrylamide, a polyol, a polyvinylpyrrolidone, a polysaccharide, or a water-soluble fluoride-bearing polymer. The present invention also relates to a porous hydrogel made with the use of the non-amphiphile-based water-in-water emulsion. The present invention further relates to using the emulsion and hydrogel for various applications.

  本发明涉及一种非两亲性基材的水包水乳液组合物。该非两亲性基材的水包水乳液组合物包括水溶性聚合物、被水溶性聚合物封装的非两亲性溶致液晶；和水。在一个实施例中，非两亲性溶致液晶包括但不限于溶致色浆液晶，更具体地是无钠 Cromoglicate (DSCG)。在另一个实施例中，水溶性聚合物可以包括但不限于聚丙烯酰胺、聚醇、聚乙烯吡咯烷酮、多糖或水溶性含氟聚合物。本发明还涉及一种用非两亲性基材的水包水乳液制成的多孔水凝胶。本发明进一步涉及使用该乳液和水凝胶用于各种应用。
• SYSTEM AND METHOD FOR CONTROLLING GROWTH OF MICROORGANISMS WITH BROMINATED FURANONES
  申请人：Luk Yan-Yeung

  公开号：US20100120905A1

  公开（公告）日：2010-05-13

  A method for inhibiting the growth of a microorganism using an effective amount of one or more of the following synthetic brominated furanones: (i) 4-bromo-5Z-(bromomethylene)-3-methylfuran-2-one; (ii) 3-(dibromomethyl)-5-(dibromomethylene)furan-2-one; (iii) 3-(bromomethyl)-5-(dibromomethylene)furan-2-one; (iv) 4-bromo-3-(bromomethyl)-5Z-(bromomethylene)furan-2-one; or (v) 4-bromo-5-(dibromomethyl)-3-methylfuran-2(5H)-one. The brominated furanones inhibit the growth of both fungi and bacteria, including the fungal species Candida albicans, Gloeophyllum trabeum, Chaetomium globosum , and Trametes versicolor and the bacterial species Pseudomonas aeruginosa . The brominated furanones can be used topically or internally to treat human infections, and can be used to treat other objects, such as wood building supplies, to prevent fungal rot.

  使用以下合成溴化呋喃酮之一或多个有效量，抑制微生物的生长：（i）4-溴-5Z-（溴甲烯基）-3-甲基呋喃-2-酮；（ii）3-（二溴甲基）-5-（二溴甲烯基）呋喃-2-酮；（iii）3-（溴甲基）-5-（二溴甲烯基）呋喃-2-酮；（iv）4-溴-3-（溴甲基）-5Z-（溴甲烯基）呋喃-2-酮；或（v）4-溴-5-（二溴甲基）-3-甲基呋喃-2（5H）-酮。 溴化呋喃酮抑制真菌和细菌的生长，包括真菌物种Candida albicans，Gloeophyllum trabeum，Chaetomium globosum和Trametes versicolor，以及细菌物种Pseudomonas aeruginosa。 溴化呋喃酮可用于局部或内部治疗人类感染，并可用于治疗其他物体，例如木材建筑用品，以预防真菌腐烂。
• Synthesis and Reactivity of Dihalofuranones
  作者：Timothy P. O'Sullivan、Thérèse A. Lyons、Cormac G.M. Gahan

  DOI：10.2174/1570178618666211027103633

  日期：2022.8

  Halogenated furanones have been found to act as potent quorum sensing inhibitors in several bacterial species. It is believed that dihalofuranones covalently bind to the LuxS enzyme, which is necessary for autoinducer-2 synthesis. In addition to their antimicrobial activity, halogenated furanones also possess anti-cancer, antioxidant, and depigmentation properties. However, traditional routes to these compounds are low-yielding and capricious.

  The aim of this study was to investigate higher-yielding preparations of gemdihalofuranones and compare their reactivity using Suzuki chemistry.

  Ramirez dibromoolefination of maleic anhydride was optimised using a variety of conditions. A similar route was investigated for the preparation of bromofluorofuranones and dichlorofuranones. The conversion of a dichlorofuranone to the corresponding iodofuranone derivatives using microwave-assisted Finkelstein chemistry was also studied. Lastly, the reactivity of the different dihalofuranones was compared by Pd-mediated coupling with phenylboronic acid.

  A higher-yielding, concise synthesis of dibromofuranones was developed using a modified Ramirez reaction. Additionally, a telescoped preparation of dichlorofuranone was higher yielding than previous approaches. Bromine- and iodine-substituted dihalofuranones proved more reactive than their chlorine-substituted analogues.

  Higher yielding routes to bromine-, fluorine-, chlorine- and iodine-containing dihalofuranones were successfully developed. Suzuki couplings of gem-dihalofuranones were found to proceed with high stereoselectivity.

  背景：已经发现卤代呋喃酮在几种细菌物种中作为强力的群体感应抑制剂。据信二卤代呋喃酮与LuxS酶共价结合，后者对于自发诱导素-2的合成是必需的。除了它们的抗微生物活性外，卤代呋喃酮还具有抗癌、抗氧化和美白的特性。然而，传统的合成这些化合物的方法产率低且难以控制。 目的：本研究旨在研究高产率的制备双卤代呋喃酮，并比较它们在铃木化学中的反应性。 方法：通过使用各种条件来优化Ramirez二溴代烯丙酸酐的制备。还研究了类似的方法来制备溴氟代呋喃酮和二氯代呋喃酮。还研究了使用微波辅助的Finkelstein化学方法将二氯代呋喃酮转化为相应的碘代呋喃酮衍生物。最后，通过Pd介导的与苯基硼酸的偶联反应比较了不同双卤代呋喃酮的反应性。 结果：使用改进的Ramirez反应开发了高产率、简洁的二溴代呋喃酮合成方法。此外，望远镜式的二氯代呋喃酮制备方法比以前的方法产率更高。溴和碘取代的双卤代呋喃酮比其氯取代的类似物更具反应性。 结论：成功地开发了制备含溴、氟、氯和碘的双卤代呋喃酮的高产率路线。发现宝石双卤代呋喃酮的铃木偶联反应具有高立体选择性。
• Synthesis and evaluation of novel furanones as biofilm inhibitors in opportunistic human pathogens
  作者：Andromeda-Celeste Gómez、Thérèse Lyons、Uwe Mamat、Daniel Yero、Marc Bravo、Xavier Daura、Osama Elshafee、Sascha Brunke、Cormac G.M. Gahan、Michelle O'Driscoll、Isidre Gibert、Timothy P. O'Sullivan

  DOI：10.1016/j.ejmech.2022.114678

  日期：2022.11
• PATIENT INTERFACE
  申请人：KONINKLIJKE PHILIPS N.V.

  公开号：US20160317771A1

  公开（公告）日：2016-11-03

  Patient interface ( 50 ) optically indicating a user that a member ( 22 ) of the patient interface ( 50 ) needs to be replaced due to wear. In particular, it relates to a member ( 22 ) for patient interface ( 50 ) which comprises at least one functional material ( 32, 34 ) having a predefined functionality and at least one indicator ( 28, 30 ) wherein the concentration of said at least one indicator ( 28, 30 ) in said member ( 22 ) correlates with the predefined functionality of said at least one functional material ( 32, 34 ).