4-hydroxy-6-methyl-2-pyrone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-hydroxy-6-methyl-2-pyrone
• 英文别名: 5-Hydroxy-3-methylpyran-2-one；5-hydroxy-3-methylpyran-2-one
• 化学式: C₆H₆O₃
• 分子量: 126.112
• InChiKey: AZJRVCZONRSRSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxy-6-methyl-2-pyrone 在 4-二甲氨基吡啶 、 N,N'-二异丙基碳二亚胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 、 甲苯 为溶剂， 反应 10.0h， 生成 6-(4-((t-butyldimethylsilyl)oxy)butyl)-4-hydroxy-3-propionyl-2H-pyran-2-one
  参考文献：
  名称：

  Novel Hybrid-Type Antimicrobial Agents Targeting the Switch Region of Bacterial RNA Polymerase

  摘要：

  The bacterial RNA polymerase (RNAP) is an ideal target for the development of antimicrobial agents against drug-resistant bacteria. Especially, the switch region within RNAP has been considered as an attractive binding site for drug discovery. Here, we designed and synthesized a series of novel hybrid-type inhibitors of bacterial RNAP. The antimicrobial activities were evaluated using a paper disk diffusion assay, and selected derivatives were tested to determine their MIC values. The hybrid-type antimicrobial agent 29 showed inhibitory activity against Escherichia coli RNAP. The molecular docking study suggested that the RNAP switch region would be the binding site of 29.

  DOI：

  10.1021/ml300350p

文献信息

• Lactic acid as an invaluable bio-based solvent for organic reactions
  作者：Jie Yang、Jia-Neng Tan、Yanlong Gu

  DOI：10.1039/c2gc36083g

  日期：——

  3-dicarbonyl compounds. In these reactions, lactic acid solvent exhibited many advantages including bio-based origin, superior synthetic efficiency, ease of isolating the product and good recyclability of the reaction medium. The concept of using lactic acid as a green solvent not only enriches the diversity and versatility of bio-based green solvents, but also offers us an effective means for designing

  乳酸 首次用作生物基绿色 溶剂 促进一些有机反应，例如三组分反应 苯乙烯类， 甲醛和活性酚化合物或N，N-二烷基乙酰乙酰胺，三组分反应乙炔二羧酸二乙酯， 苯胺 和芳香的 醛类， 苯胺醛与水杨醛的催化缩合反应 乙炔二羧酸二乙酯，以及取代的合成 喹啉 通过Friedländer环空 2'-氨基苯乙酮和1，3-二羰基化合物。在这些反应中乳酸 溶剂展示了许多优势，包括基于生物的来源，优异的合成效率，易于分离产物以及反应介质具有良好的可回收性。使用的概念乳酸 作为绿色 溶剂 不仅丰富了生物基绿色的多样性和多功能性 溶剂，但也为我们提供了一种设计对环境无害的合成系统的有效方法。
• [EN] SUBSTITUTED 4-PYRIDONES AND THEIR USE AS INHIBITORS OF NEUTROPHIL ELASTASE ACTIVITY<br/>[FR] 4-PYRIDONES SUBSTITUÉES ET LEUR UTILISATION COMME INHIBITEURS DE L'ACTIVITÉ DE L'ÉLASTASE NEUTROPHILE
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2014029830A1

  公开（公告）日：2014-02-27

  This invention relates to substituted 4-pyridones of formula (1) and their use as inhibitors of neutrophil elastase activity, pharmaceutical compositions containing the same, and methods of using the same as agents for treatment and/or prevention of pulmonary, gastrointestinal and genitourinary diseases, inflammatory diseases of the skin and the eye and other auto-immune and allergic disorders, allograft rejection, and oncological diseases.

  本发明涉及式（1）的取代4-吡啶酮及其用作中性粒细胞弹性蛋白酶活性抑制剂，含有相同物质的药物组合物，以及将其用作治疗和/或预防肺部、消化道和泌尿道疾病、皮肤和眼睛的炎症性疾病以及其他自身免疫和过敏性疾病、移植排斥反应和肿瘤性疾病的药剂的方法。
• An efficient green chemical approach for the synthesis of structurally diverse spiroheterocycles with fused heterosystems
  作者：Anand Kumar Arya、Mahendra Kumar

  DOI：10.1039/c1gc00008j

  日期：——

  Structurally diverse spiroheterocycles with fused heterosystems; spiro[benzothiazolo[2,3-b] chromeno[3,4-e]pyrimidine-7,3′-indoline]-2′,6-diones, spiro[benzothiazolo[2,3-b]pyrimido[5,4-e]pyrimidine-5,3′-indoline]-2,2′,4-triones, spiro[benzothiazolo[2,3-b]quinazolin-5,3′-indoline]-2′,4-diones and spiro[benzothiazolo[2,3-b]pyrano[3,4-e]pyrimidine-5,3′-indoline]-2′,4-diones incorporating medicinally privileged heterosystems have been synthesized by an environmentally benign, efficient and convenient synthesis involving the sulfamic acid-catalyzed multicomponent domino reaction of 2-aminobenzothiazoles with isatin and cyclic 1,3-diketones in an aqueous medium.

  结构多样的具有融合杂系统的螺杂环；螺[苯并噻唑并[2,3-b]色烯并[3,4-e]嘧啶-7,3′-吲哚啉]-2′,6-二酮、螺[苯并噻唑并[2,3-b]嘧啶并[5,4-e]嘧啶-5,3′-吲哚啉]-2、2′，4-三酮、螺[苯并噻唑并[2,3-b]喹唑啉-5,3′-吲哚啉]-2′，4-二酮和螺[苯并噻唑并[2,3-b]吡喃并[3,4-e]嘧啶-5,3′-吲哚啉]-2′、通过氨基磺酸催化的多组分多米诺反应，2-氨基苯并噻唑与异靛红和环状 1,3-二酮在水介质中合成了具有药用价值的 4-二酮杂环。
• Design, synthesis and biological evaluation of 4-(alkyloxy)-6-methyl-2H-pyran-2-one derivatives as quorum sensing inhibitors
  作者：Suzie Park、Han-Shin Kim、Kiwon Ok、YunHye Kim、Hee-Deung Park、Youngjoo Byun

  DOI：10.1016/j.bmcl.2015.05.054

  日期：2015.8

  Novel pyrone-derived quorum sensing (QS) ligands to inhibit the binding of OdDHL to the LasR of Pseudomonas aeruginosa were designed, synthesized and evaluated. Among the analogs, the most potent compound 8 exhibited strong in vitro inhibitory activities against biofilm formation and down-regulated OdDHL/LasR-associated genes by 35–67%. The binding mode of 8 in silico was highly similar to that of

  设计，合成和评估新型的吡喃衍生的群体感应（QS）配体，以抑制OdDHL与铜绿假单胞菌的LasR的结合。在这些类似物中，最有效的化合物8对生物膜形成具有强大的体外抑制活性，并且OdDHL / LasR相关基因的表达下调了35-67％。8在计算机上的结合模式与LasR活性位点中的晶体配体OdDHL的结合模式高度相似。
• One-Pot Synthesis of Macrocyclic Di- and Tetralactones Using [2+2] Photocycloaddition Reactions of Di-2-pyrones with α,ω-Diolefins
  作者：Tetsuro Shimo、Kazuya Kawabata、Hideki Miyauchi、Hui Min Zhang

  DOI：10.3987/com-11-12378

  日期：——

  Sensitized photocycloaddition reactions of 6,6'-dimethyl-4,4' -[1,4-bis(methylenoxy)phenylene]-di-pyrone (1) with poly(ethyleneglycol)divinyl ethers (2a, b) or 2,2'-dimethyltrimethylene dimethacrylate (4), together with the reactions of 6,6'-dimethyl-4,4'-polymethylenedioxy-2-pyrones (6a, b) with 4 were described. The reactions of 1 with 2a, b gave crown ether type macrocyclic compounds (3a and 3a' (isomer of 3a), 3b and 3b' (isomer of 3b)) possessing 19- and 22-membered rings across the C3-C4 and C3'-C4' double bonds in 1, respectively. Similar reactions of 1 with 4 and 6a, b with 4 afforded different types of macrocycles (5 and 5', 7a, b and 7a', b') having 19- to 21-membered rings across the C5-C6 and C5'-C6' double bonds in 2-pyrone ring. The stereochemical features of 3a' and 5 were determined by X-ray crystal analysis. The reaction mechanism was inferred by MO methods.