5-(dibromomethylene)-2(5H)-furanone | 32323-44-7

• 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)-2(5H)-furanone
• 英文别名: 5-(dibromomethylene)furan-2(5H)-one；γ-(dibromomethylene)butenolide；5-dibromomethylene-5H-furan-2-one；5-Dibrommethylen-5H-furan-2-on；5,5-Dibrom-pentadien-(2,4)-olid-(1,4)；5,5-Dibromprotoanemonin；2(5H)-Furanone, 5-(dibromomethylene)-；5-(dibromomethylidene)furan-2-one
• CAS: 32323-44-7
• 化学式: C₅H₂Br₂O₂
• 分子量: 253.878
• InChiKey: BDLMXHQRTQCETQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  9
• 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：

  5-(dibromomethylene)-2(5H)-furanone 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 三苯胂 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成 (Z)-5-phenyl-2,4-pentadien-4-olide
  参考文献：
  名称：

  A Novel Access to γ-Alkylidenebutenolides: Sequential Stille Couplings of Dibromomethylenebutenolides

  摘要：

  δ-（二溴亚甲基）丁烯内酯（2）和δ-²-溴-δ-（溴亚甲基）丁烯内酯（Z-5）均由二溴乙酰丙酸（6）一步制得，它们在 Pd 催化下与苯基或苯乙烯基三丁基锡烷发生偶联反应，得到具有极佳立体和区域控制的单溴丁烯内酯。通过第二次 Stille 偶联或与 Zn 粉尘的还原反应，可得到不含溴的δ-亚烷基丁烯酸单立体异构体。

  DOI：

  10.1055/s-2003-44997
• 作为产物：
  描述：

  3,5-二溴-4-氧代戊酸 在 硫酸 作用下， 反应 0.1h， 以28%的产率得到5-(dibromomethylene)-2(5H)-furanone
  参考文献：
  名称：

  A Novel Access to γ-Alkylidenebutenolides: Sequential Stille Couplings of Dibromomethylenebutenolides

  摘要：

  δ-（二溴亚甲基）丁烯内酯（2）和δ-²-溴-δ-（溴亚甲基）丁烯内酯（Z-5）均由二溴乙酰丙酸（6）一步制得，它们在 Pd 催化下与苯基或苯乙烯基三丁基锡烷发生偶联反应，得到具有极佳立体和区域控制的单溴丁烯内酯。通过第二次 Stille 偶联或与 Zn 粉尘的还原反应，可得到不含溴的δ-亚烷基丁烯酸单立体异构体。

  DOI：

  10.1055/s-2003-44997
• 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

• METHYLENE FURANONE DERIVATIVES AND USE OF SAID DERIVATIVES AS A PHOTOPROTECTING OR ANTIOXIDANT OR DEPIGMENTATION AGENT IN COSMETIC OR DERMATOLOGICAL COMPOSITIONS
  申请人：Marchal Estelle

  公开号：US20110184059A1

  公开（公告）日：2011-07-28

  The present invention relates to novel methylene furanone derivatives as well as the use thereof as a protective, antioxidant, or depigmentation agent in cosmetic or dermatological compositions. The invention also relates to a method for preparing said derivatives involving a Suzuki-Miyaura coupling reaction from corresponding dibromofuranone derivatives. The invention also relates to a method of preparation involving a coupling reaction of 2-methoxy-furan derivatives with a ketone followed by dehydration.

  本发明涉及新型亚甲基呋喃酮衍生物，以及其作为化妆品或皮肤科组合物中的保护剂、抗氧化剂或脱色剂的用途。该发明还涉及一种制备所述衍生物的方法，涉及从相应的二溴呋喃酮衍生物中进行Suzuki-Miyaura偶联反应的方法。该发明还涉及一种涉及2-甲氧基呋喃衍生物与酮进行偶联反应，然后脱水的制备方法。
• 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。
• B. ANTHRACIS PREVENTION AND TREATMENT: MUTANT B. ANTHRACIS LACKING LUXS ACTIVITY AND FURANONE INHIBITION OF GROWTH, AI-2 QUORUM SENSING, AND TOXIN PRODUCTION
  申请人：Jones Marcus B.

  公开号：US20080299153A1

  公开（公告）日：2008-12-04

  The present invention pertains to the discovery that B. anthracis possesses a luxS gene that encodes a functional LuxS polypeptide, and that B. anthracis synthesizes a functional AI-2 quorum-sensing molecule. The invention provides mutant B. anthracis bacteria lacking the function of the luxS gene, which do not produce a functional AI-2 molecule and have growth defects compared to wild-type B. anthracis . The invention also concerns methods for inhibiting the growth of B. anthracis , or for preventing or treating B. anthracis infection, by inhibiting the activity of the B. anthracis LuxS polypeptide, or by exposure of the B. anthracis to furanone. In particular, the invention concerns the use of furanone, a compound that inhibits AI-2-mediated quorum-sensing, to inhibit the growth of B. anthracis , to inhibit B. anthracis toxin production, particularly that of protective antigen, and to prevent or treat B. anthracis infection. The invention also provides methods to prevent B. anthracis infection, or enhance an immune response to B. anthracis infection, by administering a vaccine comprising a B. anthracis cell in which the luxS gene is mutated.

  本发明涉及到的发现是B. anthracis拥有一个编码功能性LuxS多肽的luxS基因，并且B. anthracis合成功能性AI-2类群体感应分子。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B. anthracis相比有生长缺陷的突变B. anthracis细菌。本发明还涉及通过抑制B. anthracis LuxS多肽的活性或暴露于呋喃酮来抑制B. anthracis的生长，或预防或治疗B. anthracis感染的方法。特别是，本发明涉及使用呋喃酮这种抑制AI-2介导的类群体感应的化合物来抑制B. anthracis的生长，抑制B. anthracis毒素的产生，特别是保护性抗原的产生，并预防或治疗B. anthracis感染。本发明还提供了通过给予包含luxS基因突变的B. anthracis细胞的疫苗来预防B. anthracis感染或增强对B. anthracis感染的免疫反应的方法。
• B. anthracis prevention and treatment: mutant B. anthracis lacking luxs activity and furanone inhibition of growth, AI-2 quorum sensing, and toxin production
  申请人：New York University

  公开号：US07955596B2

  公开（公告）日：2011-06-07

  The present invention pertains to the discovery that B. anthracis possesses a luxS gene that encodes a functional LuxS polypeptide, and that B. anthracis synthesizes a functional AI-2 quorum-sensing molecule. The invention provides mutant B. anthracis bacteria lacking the function of the luxS gene, which do not produce a functional AI-2 molecule and have growth defects compared to wild-type B. anthracis. The invention also concerns methods for inhibiting the growth of B. anthracis, or for preventing or treating B. anthracis infection, by inhibiting the activity of the B. anthracis LuxS polypeptide, or by exposure of the B. anthracis to furanone. In particular, the invention concerns the use of furanone, a compound that inhibits AI-2-mediated quorum-sensing, to inhibit the growth of B. anthracis, to inhibit B. anthracis toxin production, particularly that of protective antigen, and to prevent or treat B. anthracis infection. The invention also provides methods to prevent B. anthracis infection, or enhance an immune response to B. anthracis infection, by administering a vaccine comprising a B. anthracis cell in which the luxS gene is mutated.

  本发明涉及发现了炭疽杆菌具有编码功能性LuxS多肽的luxS基因，并且炭疽杆菌合成了功能性的AI-2群体感应分子。该发明提供了缺乏luxS基因功能、不产生功能性AI-2分子且与野生型炭疽杆菌相比具有生长缺陷的突变型炭疽杆菌细菌。该发明还涉及通过抑制炭疽杆菌LuxS多肽的活性或将炭疽杆菌暴露于呋喃酮中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。特别是，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。该发明还提供了通过给予包含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。
• 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。

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