3-环戊基-1,1,1-三氟-3-苯基丙烷-2-酮 | 922527-34-2

• 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: 3-环戊基-1,1,1-三氟-3-苯基丙烷-2-酮
• 英文名称: 3-cyclopentyl-1,1,1-trifluoro-3-phenylpropan-2-one
• 英文别名: 3-Cyclopentyl-1,1,1-trifluoro-3-phenylpropan-2-one
• CAS: 922527-34-2
• 化学式: C₁₄H₁₅F₃O
• 分子量: 256.268
• InChiKey: POCWBQUPMRFWPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  三氟乙酸乙酯 、 α-苯基环戊基乙酸 在 lithium diisopropyl amide 、 盐酸 作用下， 以 四氢呋喃 、 环己烷 、 水 为溶剂， 反应 0.25h， 以72%的产率得到3-环戊基-1,1,1-三氟-3-苯基丙烷-2-酮
  参考文献：
  名称：

  Trifluoromethyl Ketones from Enolizable Carboxylic Acids via Enediolate Trifluoroacetylation/Decarboxylation

  摘要：

  Primary and secondary (enolizable) carboxylic acids were converted in a single step to trifluoromethyl ketones. Treatment of the acid with 2.2 equiv of LDA generated an enediolate that was trifluoroacetylated with EtO2CCF3. Quenching the reaction mixture with aqueous HCI resulted in rapid decarboxylation and provided the trifluoromethyl ketone product in good yield. The process may be performed at -20 degrees C with a slight reduction in yield. The reaction was extended to the preparation of pentafluoroethyl and chlorodifluoromethyl ketones.

  DOI：

  10.1021/jo801737c

文献信息

• Direct conversion of primary and secondary carboxylic acids to trifluoromethyl ketones
  作者：Jonathan T. Reeves、Fabrice Gallou、Jinhua J. Song、Zhulin Tan、Heewon Lee、Nathan K. Yee、Chris H. Senanayake

  DOI：10.1016/j.tetlet.2006.11.068

  日期：2007.1

  Primary and secondary carboxylic acids were converted in one step to the corresponding trifluoromethyl ketones by treatment with trifluoroacetic anhydride (TFAA) and pyridine in toluene at 60–100 °C followed by hydrolysis/decarboxylation with water at 45 °C.

  通过在60–100°C下用三氟乙酸酐（TFAA）和吡啶在甲苯中处理，然后在45°C的水中进行水解/脱羧，一步一步将伯和仲羧酸转化为相应的三氟甲基酮。
• Synthesis of Trifluoromethyl Ketones from Carboxylic Acids: 4-(3,4-Dibromophenyl)-1,1,1-trifluoro-4-methylpentan-2-one
  作者：Reeves, Jonathan T.、Tan, Zhulin、Fandrick, Daniel R.、Song, Jinhua J.、Yee, Nathan K.、Senanayake, Chris H.

  DOI：10.15227/orgsyn.089.0210

  日期：——
• Trifluoromethyl Ketones from Enolizable Carboxylic Acids via Enediolate Trifluoroacetylation/Decarboxylation
  作者：Jonathan T. Reeves、Jinhua J. Song、Zhulin Tan、Heewon Lee、Nathan K. Yee、Chris H. Senanayake

  DOI：10.1021/jo801737c

  日期：2008.12.5

  Primary and secondary (enolizable) carboxylic acids were converted in a single step to trifluoromethyl ketones. Treatment of the acid with 2.2 equiv of LDA generated an enediolate that was trifluoroacetylated with EtO2CCF3. Quenching the reaction mixture with aqueous HCI resulted in rapid decarboxylation and provided the trifluoromethyl ketone product in good yield. The process may be performed at -20 degrees C with a slight reduction in yield. The reaction was extended to the preparation of pentafluoroethyl and chlorodifluoromethyl ketones.