(E)-3-(6-Fluoro-4-oxo-4H-chromen-3-yl)acrylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (E)-3-(6-Fluoro-4-oxo-4H-chromen-3-yl)acrylic acid
• 英文别名: 3-(6-fluoro-4-oxochromen-3-yl)prop-2-enoic acid
• 化学式: C₁₂H₇FO₄
• 分子量: 234.184
• InChiKey: KOFJCOCNYHIPRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-3-(6-Fluoro-4-oxo-4H-chromen-3-yl)acrylic acid 在 盐酸 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 34.0h， 生成
  参考文献：
  名称：

  Synthesis and Anticholinesterase Activity of 3-{[4-Methyl-3-(4-methylpiperazin-1-yl)]pent-1-en-1-yl}-4H-chromen-4-ones

  摘要：

  A procedure has been developed and optimized for the synthesis of 3-{[4-methyl-3-(4-methylpiperazin-1-yl)]pent-1-en-1-yl}-4H-chromen-4-ones (as dihydrochlorides) by an unusual version of the Morita-Baylis-Hillman reaction. A number of the title compounds with various substituents in the chromene fragment and their deamination products have been synthesized, and their inhibitory activity against butyrylcholinesterase has been studied.

  DOI：

  10.1134/s1070363219120235
• 作为产物：
  描述：

  5-氟-2-羟基苯乙酮 在 吡啶 、 三氯氧磷 作用下， 反应 0.5h， 生成 (E)-3-(6-Fluoro-4-oxo-4H-chromen-3-yl)acrylic acid
  参考文献：
  名称：

  Discovery of Novel Chromone Derivatives Containing a Sulfonamide Moiety as Anti-ToCV Agents through the Tomato Chlorosis Virus Coat Protein-Oriented Screening Method

  摘要：

  DOI：

  10.1021/acs.jafc.1c02467

文献信息

• Synthesis of Chromone-Containing Allylmorpholines through a Morita-Baylis-Hillman-Type Reaction
  作者：Nikita M. Chernov、Roman V. Shutov、Oleg I. Barygin、Mikhail Y. Dron、Galina L. Starova、Nikolay N. Kuz'mich、Igor P. Yakovlev

  DOI：10.1002/ejoc.201801159

  日期：2018.12.6

  An unusual addition of enamines to chromone‐substituted acrylic acid is an efficient and versatile method of synthesis of allylamine derivatives. The reaction is catalyzed by amines and is highly likely of Morita–Baylis–Hillman‐type. The described compounds show combined moderate inhibitory action on BChE and antagonism towards NMDA receptors

  在色酮取代的丙烯酸中异常添加烯胺是一种高效且通用的烯丙基胺衍生物的合成方法。该反应是由胺催化的，很可能是森田-贝利斯-希尔曼型的。所述化合物显示出对BChE的适度抑制作用和对NMDA受体的拮抗作用
• Synthesis of New 4,4a-Dihydroxanthones via [4+2]-Cycloaddition Reaction
  作者：N. M. Chernov、T. V. Moroz、R. V. Shutov、N. N. Kuz’mich、A. E. Shchegolev、M. V. Sopova、I. P. Yakovlev

  DOI：10.1134/s1070363219120223

  日期：2019.12

  The effect of electronic properties of substituents in the reactants on the [4+2]-cycloaddition of 3-vinyl-chromen-4-ones (dienes) and N-vinylpyrrolidines (dienophiles) has been studied. The conditions determining the formation of 4,4a-dihydroxanthones or benzophenones as the major products have been found. The aromatization of 4,4a-dihydroxanthones via pyran ring opening has been interpreted by quantum

  已经研究了反应物中取代基的电子性质对3-乙烯基色烯-4-酮（二烯）和N-乙烯基吡咯烷酮（二亲亲烯）的[4 + 2]-环加成的影响。已经发现确定形成4,4a-二氢黄嘌呤或二苯甲酮作为主要产物的条件。通过吡喃开环将4,4a-二氢氧杂蒽芳构化已通过量子化学计算进行了解释。已分离出一系列新的4,4a-二氢黄酮和二苯甲酮衍生物。