2-phenyl-6-trifluoromethyl-cyclohexanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-phenyl-6-trifluoromethyl-cyclohexanone
• 英文别名: 2-Phenyl-6-(trifluoromethyl)cyclohexan-1-one
• 化学式: C₁₃H₁₃F₃O
• 分子量: 242.241
• InChiKey: WWQQJHXDAFIUFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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 、 6-phenyl-1-(trimethylsilyloxy)cyclohex-1-ene 在 diethylzinc 、 air 、 三乙基硼 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 25.0h， 以60%的产率得到2-phenyl-6-trifluoromethyl-cyclohexanone
  参考文献：
  名称：

  通过用二烷基锌活化使酮甲硅烷基烯醇醚自由基三氟甲基化。

  摘要：

  [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。

  DOI：

  10.1021/ol0611301

文献信息

• 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。
• 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.
• Radical trifluoromethylation of ketone Li enolates
  作者：Yoshimitsu Itoh、Koichi Mikami

  DOI：10.1016/j.tet.2006.03.115

  日期：2006.7

  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.
• Zincate-type enolate for radical α-trifluoromethylation
  作者：Yuichi Tomita、Yoshiyuki Ichikawa、Yoshimitsu Itoh、Kosuke Kawada、Koichi Mikami

  DOI：10.1016/j.tetlet.2007.10.041

  日期：2007.12

  Ketone zincate-type enolates can be applied to radical trifluoromethylation for the general synthesis of alpha-CF3-ketones, cyclopentanones in particular. The addition of diethylzinc to lithium enolates is the key in the preparation of the zincate-type enolates for efficient radical trifluoromethylation. (c) 2007 Elsevier Ltd. All rights reserved.
• 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。