6-(4-fluorophenyl)-4-hydroxy-2H-pyran-2-one | 256408-82-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 6-(4-fluorophenyl)-4-hydroxy-2H-pyran-2-one
• 英文别名: 6-(4-Fluorophenyl)-4-hydroxypyran-2-one；6-(4-fluorophenyl)-4-hydroxypyran-2-one
• CAS: 256408-82-9
• 化学式: C₁₁H₇FO₃
• 分子量: 206.173
• InChiKey: ATPSLXAGWQHKEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-甲基-2-丁烯醛 、 6-(4-fluorophenyl)-4-hydroxy-2H-pyran-2-one 在 哌啶 、 乙酸酐 作用下， 以 乙酸乙酯 为溶剂， 以83%的产率得到7-(4-Fluoro-phenyl)-2,2-dimethyl-2H-pyrano[4,3-b]pyran-5-one
  参考文献：
  名称：

  A Formal [3 + 3] Cycloaddition Reaction. Improved Reactivity Using α,β-Unsaturated Iminium Salts and Evidence for Reversibility of 6π-Electron Electrocyclic Ring Closure of 1-Oxatrienes

  摘要：

  A detailed account regarding a formal [3 + 3] cycloaddition method using 4-hydroxy-2-pyrones and 1,3-diketones is described here. This formal cycloaddition reaction or annulation reaction is synthetically useful for constructing 2H-pyranyl heterocycles. The usage of alpha,beta-unsaturated iminium salts is significant in controlling competing reaction pathways to give exclusively 2H-pyrans. Most significantly, experimental evidence is provided to support the mechanism of this reaction that involves a sequential Knoevenagel condensation and a reversible 6pi-electron electrocyclic ringclosure of 1-oxatrienes.

  DOI：

  10.1021/jo020688t
• 作为产物：
  描述：

  对氟苯甲酸甲酯 在 四甲基乙二胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， -78.0~150.0 ℃ 、399.97 Pa 条件下， 生成 6-(4-fluorophenyl)-4-hydroxy-2H-pyran-2-one
  参考文献：
  名称：

  Synthesis and UV Studies of A Small Library of 6-Aryl-4-hydroxy-2-pyrones. A Relevant Structural Feature for the Inhibitory Property of Arisugacin Against Acetylcholinesterase

  摘要：

  4-Hydroxypyrones belong to an important class of compounds not only because of their medicinal significance, but also because they represent a common structural feature among natural products that ale biologically relevant. We describe here preparations of a small library of 6-aryl-4-hydroxy-pyrones which represent structural analogs of the DE-ring of arisugacin, a potent and selective inhibitor against acetylcholinesterase. Given the structural significance of the DE-ring in the inhibitory activity of arisugacin, chemical shifts of relevant protons on the pyrone ring are compared, and distinct features in UV absorptions of these 6-aryl-4-hydroxy-pyrones are described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00847-9

文献信息

• Synthesis and antimicrobial activity of new prenylated 2-pyrone derivatives
  作者：Grace Obi、Jude C. Chukwujekwu、Fanie R. van Heerden

  DOI：10.1080/00397911.2020.1718710

  日期：2020.3.3

  Abstract A series of new monoprenylated and diprenylated 2-pyrone derivatives with different halogen substituents were synthesized from the corresponding 6-aryl-4-hydroxy-2-pyrones by prenylation reactions. The compounds were evaluated for antibacterial activity and displayed significant in vitro activity with the highest activity shown by the monoprenylated 6-aryl-2-pyrones. All the compounds except

  摘要 以相应的6-芳基-4-羟基-2-吡喃酮为原料，通过异戊二烯化反应合成了一系列具有不同卤素取代基的单异戊二烯化和二异戊二烯化2-吡喃酮衍生物。对化合物的抗菌活性进行了评估，并显示出显着的体外活性，其中单异戊二烯化 6-芳基-2-吡喃酮的活性最高。除含溴类似物外，所有化合物均对一种或多种测试细菌具有活性，其中大肠杆菌是最敏感的测试生物。由于其中八种化合物对产生耐药性 β-内酰胺酶的肺炎克雷伯菌具有显着的抗菌活性，因此对这些化合物中的每一种与氨苄青霉素之间的协同作用进行了评估。在研究的八种组合中，观察到两种化合物的协同作用，4-(3-methylbut-2-enoxy)-6-phenyl-2H-pyran-2-one 和 6-(4-fluorophenyl)-4-(3-methylbut-2-enoxy) )-2H-吡喃-2-一。两种化合物，在单个 MIC 值的一半时，都能够将氨苄青霉素组合的
• Antitumor agents 270. Novel substituted 6-phenyl-4H-furo[3,2-c]pyran-4-one derivatives as potent and highly selective anti-breast cancer agents
  作者：Yizhou Dong、Qian Shi、Kyoko Nakagawa-Goto、Pei-Chi Wu、Susan L. Morris-Natschke、Arnold Brossi、Kenneth F. Bastow、Jing-Yu Lang、Mien-Chie Hung、Kuo-Hsiung Lee

  DOI：10.1016/j.bmc.2009.11.049

  日期：2010.1

  synthesized and evaluated as novel anti-breast cancer agents. Compounds 10–13, 23, 25, and 27 showed potent inhibition against the SK-BR-3 breast cancer cell line. Importantly, 25 and 27 showed the highest cancer cell line selectivity, being approximately 100–250-fold more potent against SK-BR-3 (ED50 0.28 and 0.44 μM, respectively) compared with other cancer cell lines tested. In addition, 25 displayed

  6-Phenyl-4 H -furo [3,2 - c ]pyran-4-one 衍生物基于新 tashinlactone ( 1 ) 被合成并评估为新型抗乳腺癌药物。化合物10-13，23，25，和27显示出针对SK-BR-3乳腺癌细胞系有效抑制。重要的是，25和27显示出最高的癌细胞系选择性，与其他测试的癌细胞系相比，对 SK-BR-3（ED 50分别为 0.28 和 0.44 μM）的效力大约高出 100-250 倍。此外，25对正常乳腺细胞系 184A1 和 MCF10A 显示出低细胞毒性。化合物25和27值得在我们持续的项目中进一步研究，以生成和开发选择性抗乳腺癌药物。
• Bi(OTf)₃-promoted cascade annulation of hydroxy-pyranones and unsaturated γ-ketoesters for the construction of polycyclic bridged pyrano-furopyranones
  作者：Akshay B. Rathod、Balasaheb R. Borade、Pooja I. Sambherao、Ravindar Kontham

  DOI：10.1039/d3ob01862h

  日期：——

  three dimensional polycyclic bridged chromano-furopyranones and pyrano-furopyranones (closely related to bioactive natural products) via bismuth(III)-catalyzed cascade annulation of hydroxy-pyranones and unsaturated γ-ketoesters is presented. This process involves intermolecular Michael addition, intramolecular hemiketalization, lactonization, formation of one C–C bond and two C–O bonds, rings, and contiguous

  提出了一种通过铋（ III ）催化羟基吡喃酮和不饱和γ-酮酯的级联环化构建复杂三维多环桥联色并呋喃并吡喃酮和吡喃并呋喃吡喃酮（与生物活性天然产物密切相关）的有效方案。这一过程涉及分子间迈克尔加成、分子内半缩酮化、内酯化、形成一个 C-C 键和两个 C-O 键、环和连续的立体中心。
• A Formal [3 + 3] Cycloaddition Reaction. Improved Reactivity Using α,β-Unsaturated Iminium Salts and Evidence for Reversibility of 6π-Electron Electrocyclic Ring Closure of 1-Oxatrienes
  作者：Hong C. Shen、Jiashi Wang、Kevin P. Cole、Michael J. McLaughlin、Christopher D. Morgan、Christopher J. Douglas、Richard P. Hsung、Heather A. Coverdale、Aleksey I. Gerasyuto、Juliet M. Hahn、Jia Liu、Heather M. Sklenicka、Lin-Li Wei、Luke R. Zehnder、Craig A. Zificsak

  DOI：10.1021/jo020688t

  日期：2003.3.1

  A detailed account regarding a formal [3 + 3] cycloaddition method using 4-hydroxy-2-pyrones and 1,3-diketones is described here. This formal cycloaddition reaction or annulation reaction is synthetically useful for constructing 2H-pyranyl heterocycles. The usage of alpha,beta-unsaturated iminium salts is significant in controlling competing reaction pathways to give exclusively 2H-pyrans. Most significantly, experimental evidence is provided to support the mechanism of this reaction that involves a sequential Knoevenagel condensation and a reversible 6pi-electron electrocyclic ringclosure of 1-oxatrienes.
• Synthesis and UV Studies of A Small Library of 6-Aryl-4-hydroxy-2-pyrones. A Relevant Structural Feature for the Inhibitory Property of Arisugacin Against Acetylcholinesterase
  作者：Christopher J. Douglas、Heather M. Sklenicka、Hong C. Shen、David S. Mathias、Shane J. Degen、Geoffrey M. Golding、Christopher D. Morgan、Regina A. Shih、Kristen L. Mueller、Lisa M. Scurer、Erik W. Johnson、Richard P. Hsung

  DOI：10.1016/s0040-4020(99)00847-9

  日期：1999.11

  4-Hydroxypyrones belong to an important class of compounds not only because of their medicinal significance, but also because they represent a common structural feature among natural products that ale biologically relevant. We describe here preparations of a small library of 6-aryl-4-hydroxy-pyrones which represent structural analogs of the DE-ring of arisugacin, a potent and selective inhibitor against acetylcholinesterase. Given the structural significance of the DE-ring in the inhibitory activity of arisugacin, chemical shifts of relevant protons on the pyrone ring are compared, and distinct features in UV absorptions of these 6-aryl-4-hydroxy-pyrones are described. (C) 1999 Elsevier Science Ltd. All rights reserved.