ethyl 2-(4-acetylphenyl)-2-oxoacetate | 1417619-13-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-(4-acetylphenyl)-2-oxoacetate
• 英文别名: (4-acetylphenyl)oxoacetic acid ethyl ester；Ethyl 2-(4-acetylphenyl)-2-oxoacetate
• CAS: 1417619-13-6
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: FYMDTGFMYIKOLN-UHFFFAOYSA-N

物化性质

• 沸点：
  357.7±25.0 °C(predicted)
• 密度：
  1.165±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4-acetylphenyl)-2-oxoacetate 在 双(三甲基硅烷基)氨基钾 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.25h， 生成 2-(4-Acetylphenyl)prop-2-enoic acid
  参考文献：
  名称：

  缺电子烯烃的导向基团辅助的铜催化烯烃三氟甲基化

  摘要：

  提供的协助：标题反应中的引导基团不仅激活底物，而且还允许顺式三氟甲基化产物的立体定向形成。该反应操作简单并耐受多种官能团的，从而提供了β-CF的立体选择性合成的有效方法，3 -官能化的丙烯酰胺衍生物。

  DOI：

  10.1002/anie.201307245
• 作为产物：
  描述：

  ethyl 2-(4-acetylphenyl)-2-nitroacetate 在 potassium fluoride 、 四丁基氟化铵 、 碘甲烷 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以51%的产率得到ethyl 2-(4-acetylphenyl)-2-oxoacetate
  参考文献：
  名称：

  2-Aryl-2-nitroacetates as Central Precursors to Aryl Nitromethanes, α-Ketoesters, and α-Amino Acids

  摘要：

  Nitroarylacetates are useful small molecular building blocks that act as precursors to alpha-ketoesters and aryl nitromethanes as well as alpha-amino acids. Methods were developed that produce each of these compound types in good yields. Two different conditions for decarboxylation are discussed for substrates with neutral and electron-poor aryl groups versus electron-rich aryl groups. For formation of the alpha-ketoesters, new mild conditions for the Nef disproportionation were identified.

  DOI：

  10.1021/jo302071s

文献信息

• In Situ Generated Ag^II-Catalyzed Selective Oxo-Esterification of Alkyne with Alcohol to α-Ketoester: Photophysical Study
  作者：Radha M. Laha、Saikat Khamarui、Saikat K. Manna、Dilip K. Maiti

  DOI：10.1021/acs.orglett.5b03484

  日期：2016.1.4

  An expert and easy one-step catalytic method for the multi O-C coupling of alkyne is developed for the synthesis of valuable alpha-ketoesters and their chiral analogues, in contrast to the generation of esters by a noncatalytic method. The in situ generated powerful Ag-II catalyst from AgOTf is the workhorse in the oxidative grafting of alkyne with PhIO and alcohol. The radical mechanism is confirmed in our controlled experiments and UV-vis study.
• Directing-Group-Assisted Copper-Catalyzed Olefinic Trifluoromethylation of Electron-Deficient Alkenes
  作者：Chao Feng、Teck-Peng Loh

  DOI：10.1002/anie.201307245

  日期：2013.11.18

  Assistance provided: The directing group in the title reaction not only activates the substrates but also allows the stereospecific formation of cis‐trifluoromethylated products. The reaction is operationally simple and tolerates a wide variety of functional groups, thus providing an efficient method for the stereoselective synthesis of β‐CF3‐functionalized acrylamide derivatives.

  提供的协助：标题反应中的引导基团不仅激活底物，而且还允许顺式三氟甲基化产物的立体定向形成。该反应操作简单并耐受多种官能团的，从而提供了β-CF的立体选择性合成的有效方法，3 -官能化的丙烯酰胺衍生物。
• 2-Aryl-2-nitroacetates as Central Precursors to Aryl Nitromethanes, α-Ketoesters, and α-Amino Acids
  作者：Alison E. Metz、Marisa C. Kozlowski

  DOI：10.1021/jo302071s

  日期：2013.1.18

  Nitroarylacetates are useful small molecular building blocks that act as precursors to alpha-ketoesters and aryl nitromethanes as well as alpha-amino acids. Methods were developed that produce each of these compound types in good yields. Two different conditions for decarboxylation are discussed for substrates with neutral and electron-poor aryl groups versus electron-rich aryl groups. For formation of the alpha-ketoesters, new mild conditions for the Nef disproportionation were identified.