4-(2-(2-aminoethoxy)ethoxy)-2,5-dimethyl-3(2H)-furanone | 1400789-60-7

• 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: 4-(2-(2-aminoethoxy)ethoxy)-2,5-dimethyl-3(2H)-furanone
• 英文别名: 4-(2-(2-aminoethoxy)ethoxy)-2,5-dimethylfuran-3(2H)-one；4-[2-(2-Aminoethoxy)ethoxy]-2,5-dimethylfuran-3-one；4-[2-(2-aminoethoxy)ethoxy]-2,5-dimethylfuran-3-one
• CAS: 1400789-60-7
• 化学式: C₁₀H₁₇NO₄
• 分子量: 215.249
• InChiKey: DQBQRYJNRKSAKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tert-butyl N-[2-[2-(2,5-dimethyl-4-oxofuran-3-yl)oxyethoxy]ethyl]carbamate 在 磷酸 、 水 作用下， 以 甲苯 为溶剂， 以78%的产率得到4-(2-(2-aminoethoxy)ethoxy)-2,5-dimethyl-3(2H)-furanone
  参考文献：
  名称：

  Immobilized Furanone Derivatives as Inhibitors for Adhesion of Bacteria on Modified Poly(styrene-co-maleic anhydride)

  摘要：

  The ability of brominated furanones and other furanone compounds with 2(3H) and 2(5H) cores to inhibit bacterial adhesion of surfaces as well deactivate (destroy) them has been previously reported. The furanone derivatives 4-(2-(2-aminoethoxy)-2,5-dimethyl-3(2H)-furanone and 5-(2-(2-aminoethoxy)-ethoxy)methyl)-2(5H)-furanone were synthesized in our laboratory. These furanone derivatives were then covalently immobilized onto poly(styrene-co-maleic anhydride) (SMA) and electrospun to fabricate nonwoven nanofibrous mats with antimicrobial and cell-adhesion inhibition properties. The electrospun nanofibrous mats were tested for their ability to inhibit cell attachment by strains of bacteria commonly found in water (Klebsiella pneumoniae Xen 39, Staphylococcus aureus Xen 36, Escherichia colt Xen 14, Pseudomonas aeruginosa Xen 5, and Salmonella tymphimurium Xen 26). Proton nuclear magnetic resonance spectroscopy H-1 NMR), electrospray mass spectroscopy (ES-MS), and attenuated total reflectance Fourier transform infrared spectroscopy (ATR-FTIR) were used to confirm the structures of the synthesized furanones as well as their successful immobilization on SMA. To ascertain that the immobilized furanone compounds do not leach into filtered water, samples of water, filtered through the nanofibrous mats were analyzed using gas chromatography coupled with mass spectroscopy (GC-MS). The morphology of the electrospun nanofibers was characterized using scanning electron microscopy (SEM).

  DOI：

  10.1021/bm300932u

文献信息

• A FURANONE CONTAINING POLYMER COMPOUND WITH BACTERIA-ADHESION PROPERTIES
  申请人：Stellenbosch University

  公开号：EP2875057B1

  公开（公告）日：2016-11-02
• US9457321B2
  申请人：——

  公开号：US9457321B2

  公开（公告）日：2016-10-04
• [EN] A FURANONE CONTAINING POLYMER COMPOUND WITH BACTERIA-ADHESION PROPERTIES<br/>[FR] COMPOSÉ POLYMÈRE CONTENANT UNE FURANONE AYANT DES PROPRIÉTÉS D'ADHÉRENCE AUX BACTÉRIES
  申请人：UNIV STELLENBOSCH

  公开号：WO2014013475A9

  公开（公告）日：2014-03-27

  [EN] A polymer compound (I) with bacteria-adhesion inhibition properties against bacteria such as P. aeruginosa Xen 5, E. coli Xen 14, S. typhimurium Xen 26, S. aureus Xen 36 and K. pneumoniae Xen 39 is described. The group R is provided by a substituted furanone linked by an alkyl chain or, more preferably a hydrophilic moiety such as oligo(ethylene oxide) ((CH2 -CH2 -O)i ) to the polymer backbone. The group R may be the same or different along the polymer backbone. The invention also provides nanofibres and coatings which include a polymer compound as defined above.
  [FR] Cette invention concerne un composé polymère (I) doué de propriétés d'inhibition de l'adhérence aux bactéries contre des bactéries telles que P. aeruginosa Xen 5, E. coli Xen 14, S. typhimurium Xen 26, S. aureus Xen 36 et K. pneumoniae Xen 39. Le groupe R est représenté par une furanone substituée liée par une chaîne alkyle ou, plus préférablement un fragment hydrophile tel qu'un oligo(oxyde d'éthylène) ((CH2 -CH2 -O)i) au squelette du polymère. Le groupe R peut être identique ou différent sur la longueur du squelette du polymère. Cette invention concerne également des nanofibres et des revêtements qui comprennent un composé polymère tel que défini ci-dessus. (I)
• Immobilized Furanone Derivatives as Inhibitors for Adhesion of Bacteria on Modified Poly(styrene-<i>co</i>-maleic anhydride)
  作者：Nonjabulo P. Gule、Osama Bshena、Michèle de Kwaadsteniet、Thomas E. Cloete、Bert Klumperman

  DOI：10.1021/bm300932u

  日期：2012.10.8

  The ability of brominated furanones and other furanone compounds with 2(3H) and 2(5H) cores to inhibit bacterial adhesion of surfaces as well deactivate (destroy) them has been previously reported. The furanone derivatives 4-(2-(2-aminoethoxy)-2,5-dimethyl-3(2H)-furanone and 5-(2-(2-aminoethoxy)-ethoxy)methyl)-2(5H)-furanone were synthesized in our laboratory. These furanone derivatives were then covalently immobilized onto poly(styrene-co-maleic anhydride) (SMA) and electrospun to fabricate nonwoven nanofibrous mats with antimicrobial and cell-adhesion inhibition properties. The electrospun nanofibrous mats were tested for their ability to inhibit cell attachment by strains of bacteria commonly found in water (Klebsiella pneumoniae Xen 39, Staphylococcus aureus Xen 36, Escherichia colt Xen 14, Pseudomonas aeruginosa Xen 5, and Salmonella tymphimurium Xen 26). Proton nuclear magnetic resonance spectroscopy H-1 NMR), electrospray mass spectroscopy (ES-MS), and attenuated total reflectance Fourier transform infrared spectroscopy (ATR-FTIR) were used to confirm the structures of the synthesized furanones as well as their successful immobilization on SMA. To ascertain that the immobilized furanone compounds do not leach into filtered water, samples of water, filtered through the nanofibrous mats were analyzed using gas chromatography coupled with mass spectroscopy (GC-MS). The morphology of the electrospun nanofibers was characterized using scanning electron microscopy (SEM).