2-氟-1-(4-硝基苯基)-2-丙烯-1-酮 | 506437-42-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氟-1-(4-硝基苯基)-2-丙烯-1-酮
• 英文名称: 2-fluoro-1-(4-nitrophenyl)-2-propen-1-one
• 英文别名: 2-Fluoro-1-(4-nitrophenyl)prop-2-en-1-one
• CAS: 506437-42-9
• 化学式: C₉H₆FNO₃
• 分子量: 195.15
• InChiKey: QZNYYBZBUGNBTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 三乙胺 作用下， 以 乙腈 为溶剂， 以0.069 g的产率得到2-氟-1-(4-硝基苯基)-2-丙烯-1-酮
  参考文献：
  名称：

  2-Fluoroenones via an Umpolung Morita–Baylis–Hillman Reaction of Enones

  摘要：

  enone-α-H to F substitution, leading to 2-fluoroenones in a single step from ubiquitous enones in 63–90% yield. The reaction is applicable to a wide range of aromatic and alkenyl enones and is carried out at room temperature using HF-pyridine complex as the fluoride source. Mechanistic investigations support that the reaction takes place through a rare umpolung Morita–Baylis–Hillman-type mechanism.

  DOI：

  10.1021/acs.orglett.3c00313

文献信息

• Palladium-Catalyzed Carbonylative Coupling of Tributyl(1-fluorovinyl)stannane with Aryl Halides and Aryl Triflates
  作者：Takeshi Hanamoto、Kumiko Handa、Tomonori Mido

  DOI：10.1246/bcsj.75.2497

  日期：2002.11

  catalytic amount of CsF in DMF in good yields. The palladium-catalyzed carbonylative cross-coupling reaction of 2 with aryl iodides bearing various functional groups smoothly proceeded giving the corresponding aryl 1-fluorovinyl ketones in good yields under an atmospheric pressure of carbon monoxide. A similar carbonylative cross-coupling reaction of 2 with aryl triflates was also accomplished in the presence

  我们发现三丁基（1-氟乙烯基）锡烷（2）可以很容易地由（1-氟乙烯基）甲基二苯基硅烷1（1）和双（三丁基锡）氧化物在DMF中催化量的CsF存在下反应制备产量。钯催化的 2 与带有各种官能团的芳基碘化物的羰基化交叉偶联反应顺利进行，在一氧化碳的大气压下以良好的产率得到相应的芳基 1-氟乙烯基酮。2 与芳基三氟甲磺酸酯的类似羰基化交叉偶联反应也在四丁基碘化铵 (Bu4NI) 作为添加剂的存在下完成。
• 2-Fluoroenones via an Umpolung Morita–Baylis–Hillman Reaction of Enones
  作者：Subrata Maity、Alex M. Szpilman

  DOI：10.1021/acs.orglett.3c00313

  日期：2023.2.24

  enone-α-H to F substitution, leading to 2-fluoroenones in a single step from ubiquitous enones in 63–90% yield. The reaction is applicable to a wide range of aromatic and alkenyl enones and is carried out at room temperature using HF-pyridine complex as the fluoride source. Mechanistic investigations support that the reaction takes place through a rare umpolung Morita–Baylis–Hillman-type mechanism.