4'-(1-fluorovinyl)acetophenone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4'-(1-fluorovinyl)acetophenone
• 英文别名: 1-[4-(1-Fluoroethenyl)phenyl]ethanone
• 化学式: C₁₀H₉FO
• 分子量: 164.179
• InChiKey: HOXKLYUWYXSHNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4'-(1-fluorovinyl)acetophenone 在 叠氮基三甲基硅烷 、 Selectfluor 、 三氟乙酸 作用下， 以 水 、 乙腈 为溶剂， 以10 %的产率得到
  参考文献：
  名称：

  Radical Amido‐ and Azido‐Fluorination of α ‐Fluorostyrene Derivatives: An Innovative Approach Towards β ‐Aryl‐ β , β ‐difluoroamino Motifs

  摘要：

  AbstractAn innovative one‐step synthesis towards β‐aryl‐β,β‐difluorocarbamates and β‐aryl‐β,β‐difluoroazides is presented. The described approach relies on the use of α‐fluorostyrene substrates in a radical addition/fluorination reaction with N‐centered radicals in the presence of Selectfluor®. The best results were obtained for the azidofluorination reaction. The resultant β‐aryl‐β,β‐difluoroazides were further transformed into Nitrogen‐based heterocycles (e. g. pyrrole, triazole, and tetrazole) and in more elaborated azide derivatives.

  DOI：

  10.1002/ejoc.202201165
• 作为产物：
  描述：

  4-碘代苯乙酮 以66%的产率得到
  参考文献：
  名称：

  Matthews Donald P., Waid Philip P., Sabol Jeffrey S., McCarthy James R., Tetrahedron Lett, 35 (1994) N 29, S 5177-5180

  摘要：

  DOI：

文献信息

• Cross-Coupling Reactions of (1-Fluorovinyl)methydiphenylsilane¹ with Aryl Halides and Aryl Triflates
  作者：Takeshi Hanamoto、Tomoko Kobayashi

  DOI：10.1021/jo030111r

  日期：2003.8.1

  of functional groups (nitro, ester, ketone, and ether) on the aromatic rings can be tolerated under these mild conditions. Aryl iodides are superior to aryl bromides as the coupling reaction partner. The cross-coupling reaction of 1 with aryl triflates instead of aryl halides was also accomplished in the presence of tetrabutylammonium iodide (n-Bu(4)NI) as the additive under similar conditions.

  研究了（1-氟乙烯基）甲基二苯基硅烷（1）与芳基卤化物和芳基三氟甲磺酸酯的氟化铯（CsF）辅助交叉偶联反应。与芳基碘化物的反应平稳进行，在非质子极性溶剂（例如DMF，DMI，DMA和DFA）中，在催化量的CuI和Pd（PPh（3））（4）存在的情况下，提供了相应的（1-氟乙烯基）芳烃。 NMP产量高。在这些温和条件下，可以容忍芳香环上的各种官能团（硝基，酯，酮和醚）。作为偶联反应伙伴，芳基碘化物优于芳基溴化物。在存在四丁基碘化铵（n-Bu（4）NI）作为添加剂的情况下，在相似的条件下，也完成了1与芳基三氟甲磺酸酯而不是芳基卤化物的交叉偶联反应。
• The synthesis of (1-fluorovinyl)tributyltin: A synthetic equivalent for the 1-fluoroethene anion
  作者：Donald P. Matthews、Philip P. Waid、Jeffrey S. Sabol、James R. McCarthy

  DOI：10.1016/s0040-4039(00)77057-2

  日期：1994.7

  The synthesis of (1-fluorovinyl)tributyltin () is reported, and the utility of as a synthetic equivalent for the 1-fluoroethene anion through palladium-catalyzed couplings is demonstrated.

  报道了（1-氟乙烯基）三丁基锡（）的合成，并且证明了其通过钯催化的偶联作为1-氟乙烯阴离子的合成等同物的实用性。
• Fluoride Ion-Assisted Cross-Coupling Reactions of (α-Fluorovinyl)diphenylmethylsilane with Aryl Iodides Catalyzed by Pd(0)/Cu(I) Systems
  作者：Takeshi Hanamoto、Tomoko Kobayashi、Michio Kondo

  DOI：10.1055/s-2001-10791

  日期：——

  The palladium-catalyzed cross-coupling reactions of (α-fluorovinyl)diphenylmethylsilane with organic halides in the presence of Cu(I) halide afford good yields of α-fluorovinyl organic compounds.

  在卤化铜（I）的存在下，钯催化的（δ-氟乙烯基）二苯基甲基硅烷与有机卤化物的交叉偶联反应可以得到产率很高的δ-氟乙烯基有机化合物。
• Matthews Donald P., Waid Philip P., Sabol Jeffrey S., McCarthy James R., Tetrahedron Lett, 35 (1994) N 29, S 5177-5180
  作者：Matthews Donald P., Waid Philip P., Sabol Jeffrey S., McCarthy James R.

  DOI：——

  日期：——
• Radical Amido‐ and Azido‐Fluorination of <i>α</i> ‐Fluorostyrene Derivatives: An Innovative Approach Towards <i>β</i> ‐Aryl‐ <i>β</i> , <i>β</i> ‐difluoroamino Motifs
  作者：Alphonsine Ngo Ndimba、Émilie Vincent、Julien Brioche

  DOI：10.1002/ejoc.202201165

  日期：2022.11.18

  AbstractAn innovative one‐step synthesis towards β‐aryl‐β,β‐difluorocarbamates and β‐aryl‐β,β‐difluoroazides is presented. The described approach relies on the use of α‐fluorostyrene substrates in a radical addition/fluorination reaction with N‐centered radicals in the presence of Selectfluor®. The best results were obtained for the azidofluorination reaction. The resultant β‐aryl‐β,β‐difluoroazides were further transformed into Nitrogen‐based heterocycles (e. g. pyrrole, triazole, and tetrazole) and in more elaborated azide derivatives.

表征谱图