2-(fluoro(phenyl)methyl)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-(fluoro(phenyl)methyl)cyclohexanone
• 英文别名: 2-[Fluoro(phenyl)methyl]cyclohexan-1-one；2-[fluoro(phenyl)methyl]cyclohexan-1-one
• 化学式: C₁₃H₁₅FO
• 分子量: 206.26
• InChiKey: AIHOCCRASAIZFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 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：
  2

反应信息

• 作为产物：
  描述：

  2-苄基环己酮 在 三乙基硼 、 Selectfluor 作用下， 以 正己烷 、 乙腈 为溶剂， 反应 4.0h， 以16.667%的产率得到
  参考文献：
  名称：

  Triethylborane-Initiated Radical Chain Fluorination: A Synthetic Method Derived from Mechanistic Insight

  摘要：

  We offer a mild, metal-free sp(3) C-H fluorination alternative using Selectfluor and a substoichiometric amount of triethylborane--an established radical initiator in the presence of O2. This radical-chain-based synthetic method is particularly noteworthy as an offspring of the insight gained from a mechanistic study of copper-promoted aliphatic fluorination, constructively turning O2 from an enemy to an ally. Furthermore, BEt3/O2 is a preferred initiator in industrial processes, as it is economical, is low in toxicity, and lends way to easier workup.

  DOI：

  10.1021/jo501520e

文献信息

• Triethylborane-Initiated Radical Chain Fluorination: A Synthetic Method Derived from Mechanistic Insight
  作者：Cody Ross Pitts、Bill Ling、Ryan Woltornist、Ran Liu、Thomas Lectka

  DOI：10.1021/jo501520e

  日期：2014.9.19

  We offer a mild, metal-free sp(3) C-H fluorination alternative using Selectfluor and a substoichiometric amount of triethylborane--an established radical initiator in the presence of O2. This radical-chain-based synthetic method is particularly noteworthy as an offspring of the insight gained from a mechanistic study of copper-promoted aliphatic fluorination, constructively turning O2 from an enemy to an ally. Furthermore, BEt3/O2 is a preferred initiator in industrial processes, as it is economical, is low in toxicity, and lends way to easier workup.