2-(4-fluorophenyl)-7-methyl-4H-chromen-4-one | 324526-82-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(4-fluorophenyl)-7-methyl-4H-chromen-4-one
• 英文别名: 2-(4-fluorophenyl)-7-methylchromen-4-one
• CAS: 324526-82-1
• 化学式: C₁₆H₁₁FO₂
• 分子量: 254.261
• InChiKey: DTPKTIRCRNFQNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-fluorophenyl)-7-methyl-4H-chromen-4-one 在 劳森试剂 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 2-(4-Fluorophenyl)-7-methylchromene-4-thione
  参考文献：
  名称：

  A new series of flavones, thioflavones, and flavanones as selective monoamine oxidase-B inhibitors

  摘要：

  A new series of synthetic flavones, thioflavones, and flavanones has been synthesized and evaluated as potential inhibitors of monoamine oxidase isoforms (MAO-A and -B). The most active series is the flavanone one with higher selective inhibitory activity against MAO-B. Some of these flavanones (mainly the most effective) have been separated and tested as single enantiomers. In order to investigate the MAOs recognition of the most active and selective compounds, a molecular modeling study has been performed using available Protein Data Bank (PDB) structures as receptor models for docking experiments. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.029
• 作为产物：
  描述：

  1-(2,2-二溴乙烯基)-4-氟苯 在 dipotassium peroxodisulfate 、 正丁基锂 、 silver nitrate 作用下， 以 四氢呋喃 、 正己烷 、 水 、 乙腈 为溶剂， 反应 5.0h， 生成 2-(4-fluorophenyl)-7-methyl-4H-chromen-4-one
  参考文献：
  名称：

  银催化的双脱羧自由基炔基化/芳基丙酸与α-酮酸的环化：在温和条件下获得壬酮和黄酮的途径

  摘要：

  壬烷由于其多功能性而成为杂环衍生物的各种有机合成中的重要组成部分，而黄酮是具有广泛生物活性的重要一类天然产物。我们描述了芳基丙酸与α-酮酸的催化双脱羧炔基化反应。以Ag（I）/过硫酸盐为催化体系，可以容易地获得带有各种取代基的有价值的炔酮。邻位羟基取代基的引入α-酮酸的位点使该策略进一步适用于通过异环戊烷以类似的银催化体系以中等到良好的收率构建黄酮衍生物。反应在相对温和的反应条件下进行，并能耐受多种官能团。对照实验表明，两个反应均经历自由基过程。

  DOI：

  10.1002/adsc.201701469

文献信息

• Pd catalyzed couplings of “superactive esters” and terminal alkynes: Application to flavones and γ-benzopyranones construction
  作者：Dandan Yang、Zhenhua Wang、Xiu Wang、Huaming Sun、Zunyuan Xie、Juan Fan、Guofang Zhang、Weiqiang Zhang、Ziwei Gao

  DOI：10.1016/j.molcata.2016.10.030

  日期：2017.1

  Lewis base, N-methylmorpholine (NMM) accelerated Pd-catalyzed Sonogashira coupling of steric hindered super active esters, la-le, and terminal alkynes. This approach provided an efficient synthetic protocol for a broad array of acylated o-alkynoylphenols compounds, 3a-3e, under moderate conditions. The mechanistic study clearly demonstrated that NNM stabilized the catalytic palladium species, and accelerated the leaving of triazine moiety during the catalytic cycle of the cross-coupling reactions. In addition, piperazine was found to efficiently catalyze the 6-endo cyclization of acylated o-alkynoylphenols, which achieved the diversity oriented synthesis of gamma-benzopyranones, 4aa-4eg, with 93-99% yields. (C) 2016 Elsevier B.V. All rights reserved.
• Silver-catalyzed Double Decarboxylative Radical Alkynylation/Annulation of Arylpropiolic Acids with α-keto Acids: Access to Ynones and Flavones under Mild Conditions
  作者：Mengting Meng、Guofang Wang、Liangfeng Yang、Kai Cheng、Chenze Qi

  DOI：10.1002/adsc.201701469

  日期：2018.3.20

  Ynones are privileged building blocks in various organic syntheses of heterocyclic derivatives due to their multifunctional nature, and flavones are an important class of natural products with a wide range of biological activities. We describe the catalytic double decarboxylative alkynylation of arylpropiolic acids with α‐keto acids. With Ag(I)/persulfate as the catalysis system, the valuable ynones

  壬烷由于其多功能性而成为杂环衍生物的各种有机合成中的重要组成部分，而黄酮是具有广泛生物活性的重要一类天然产物。我们描述了芳基丙酸与α-酮酸的催化双脱羧炔基化反应。以Ag（I）/过硫酸盐为催化体系，可以容易地获得带有各种取代基的有价值的炔酮。邻位羟基取代基的引入α-酮酸的位点使该策略进一步适用于通过异环戊烷以类似的银催化体系以中等到良好的收率构建黄酮衍生物。反应在相对温和的反应条件下进行，并能耐受多种官能团。对照实验表明，两个反应均经历自由基过程。
• A new series of flavones, thioflavones, and flavanones as selective monoamine oxidase-B inhibitors
  作者：Franco Chimenti、Rossella Fioravanti、Adriana Bolasco、Paola Chimenti、Daniela Secci、Francesca Rossi、Matilde Yáñez、Francisco Orallo、Francesco Ortuso、Stefano Alcaro、Roberto Cirilli、Rosella Ferretti、M. Luisa Sanna

  DOI：10.1016/j.bmc.2009.12.029

  日期：2010.2

  A new series of synthetic flavones, thioflavones, and flavanones has been synthesized and evaluated as potential inhibitors of monoamine oxidase isoforms (MAO-A and -B). The most active series is the flavanone one with higher selective inhibitory activity against MAO-B. Some of these flavanones (mainly the most effective) have been separated and tested as single enantiomers. In order to investigate the MAOs recognition of the most active and selective compounds, a molecular modeling study has been performed using available Protein Data Bank (PDB) structures as receptor models for docking experiments. (C) 2009 Elsevier Ltd. All rights reserved.