2-methyl-6-trifluoromethyl-cyclohexanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-6-trifluoromethyl-cyclohexanone
• 英文别名: 2-Methyl-6-(trifluoromethyl)cyclohexan-1-one
• 化学式: C₈H₁₁F₃O
• mdl: MFCD08166601
• 分子量: 180.17
• InChiKey: FXWOJJUXDKHUMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.875
• 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：

  三氟碘甲烷 、 2-甲基环己酮 在 lithium diisopropyl amide 、 三乙基硼 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 2-methyl-6-trifluoromethyl-cyclohexanone
  参考文献：
  名称：

  Radical trifluoromethylation of ketone Li enolates

  摘要：

  It has generally been believed that highly basic Li enolates cannot be applied as substrates for radical trifluoromethylation due to defluorination of the alpha-CF3 product. However, Li enolates can be in fact employed for radical trifluoromethylation. Moreover, the reaction is extremely fast and the minimum reaction time is only similar to 1 s. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.115

文献信息

• Zn-mediated rhodium-catalyzed α-trifluoromethylation of ketones via silyl enol ethers
  作者：Kazuyuki Sato、Takashi Yuki、Atsushi Tarui、Masaaki Omote、Itsumaro Kumadaki、Akira Ando

  DOI：10.1016/j.tetlet.2008.04.030

  日期：2008.5

  The treatment of silyl enol ethers of ketones with CF3–I and Et2Zn in the presence of RhCl(PPh3)3 in DME gave α-trifluoromethyl ketones in good yields. The reaction can be widely applicable to silyl enol ethers derived from aliphatic or aromatic ketones. In the absence of the rhodium catalyst, the reaction was very slow and the yields were quite poor.

  在DME中，在RhCl（PPh 3）3存在下，用CF 3 –I和Et 2 Zn处理酮的甲硅烷基烯醇醚可得到高产率的α-三氟甲基酮。该反应可广泛应用于衍生自脂族或芳族酮的甲硅烷基烯醇醚。在没有铑催化剂的情况下，反应非常缓慢并且收率很差。
• Radical Trifluoromethylation of Ketone Silyl Enol Ethers by Activation with Dialkylzinc
  作者：Koichi Mikami、Yuichi Tomita、Yoshiyuki Ichikawa、Kazutoshi Amikura、Yoshimitsu Itoh

  DOI：10.1021/ol0611301

  日期：2006.10.1

  [reaction: see text] The radical trifluoromethylation of ketone silyl enol ethers gave alpha-CF(3) ketones in good yields with wide scope of the ketonic substrates including acyclic ketones and cyclopentanone. The use of dialkylzinc to activate the silyl enol ethers is the key to the efficient radical trifluoromethylation.

  [反应：见正文]酮甲硅烷基烯醇醚的自由基三氟甲基化反应可得到高产率的α-CF（3）酮，并具有广泛的酮基底物，包括无环酮和环戊酮。使用二烷基锌活化甲硅烷基烯醇醚是有效的自由基三氟甲基化的关键。
• Dialkylzinc-accelerated α-Trifluoromethylation of Carbonyl Compounds Catalyzed by Late-transition-metal Complexes
  作者：Yuichi Tomita、Yoshimitsu Itoh、Koichi Mikami

  DOI：10.1246/cl.2008.1080

  日期：2008.10.5

  Trifluoromethylation of ketone silyl enol ethers is found to be significantly accelerated by late-transition-metal catalysts and dialkylzincs to give α-trifluoromethyl ketones in good yields. Addition of dialkylzinc is the key to the high yielding α-trifluoromethylation of carbonyl compounds.

  发现后过渡金属催化剂和二烷基锌显着加速了酮甲硅烷基烯醇醚的三氟甲基化，以良好的产率生成α-三氟甲基酮。二烷基锌的加成是羰基化合物高产率α-三氟甲基化的关键。
• Facile Radical Trifluoromethylation of Lithium Enolates
  作者：Yoshimitsu Itoh、Koichi Mikami

  DOI：10.1021/ol0517574

  日期：2005.10.1

  [GRAPHICS]Highly basic lithium enolates are shown to be applicable to radical trifluoromethylation. The reaction is extremely fast, and the minimum reaction time is similar to 1 s.