3-Fluoro-3-phenyl-1-pyrrolidin-1-ylpropan-1-one | 1428331-72-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3-Fluoro-3-phenyl-1-pyrrolidin-1-ylpropan-1-one
• 英文别名: 3-fluoro-3-phenyl-1-pyrrolidin-1-ylpropan-1-one
• CAS: 1428331-72-9
• 化学式: C₁₃H₁₆FNO
• 分子量: 221.275
• InChiKey: ZHAKPXBEDIQCNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-苯基-1-(吡咯烷-1-基)丙烷-1-酮 在 iron(II) acetylacetonate 、 Selectfluor 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以41%的产率得到3-Fluoro-3-phenyl-1-pyrrolidin-1-ylpropan-1-one
  参考文献：
  名称：

  Iron(II)-Catalyzed Benzylic Fluorination

  摘要：

  Direct C-F functionalization of benzylic sp(3) C-H bonds is a synthetic challenge that has yet to be propitiously overcome. A mild, one-pot synthesis of monofluorinated benzylic substrates is reported with commercially available iron(II) acetylacetonate and Selectfluor in good to excellent yields and selectivity. A convenient route to beta-fluorinated products of 3-aryl ketones is also highlighted, providing a synthetic equivalent to the difficult to accomplish conjugate addition of fluoride to alpha,beta-unsaturated ketones.

  DOI：

  10.1021/ol400424s

文献信息

• Iron(II)-Catalyzed Benzylic Fluorination
  作者：Steven Bloom、Cody Ross Pitts、Ryan Woltornist、Andrew Griswold、Maxwell Gargiulo Holl、Thomas Lectka

  DOI：10.1021/ol400424s

  日期：2013.4.5

  Direct C-F functionalization of benzylic sp(3) C-H bonds is a synthetic challenge that has yet to be propitiously overcome. A mild, one-pot synthesis of monofluorinated benzylic substrates is reported with commercially available iron(II) acetylacetonate and Selectfluor in good to excellent yields and selectivity. A convenient route to beta-fluorinated products of 3-aryl ketones is also highlighted, providing a synthetic equivalent to the difficult to accomplish conjugate addition of fluoride to alpha,beta-unsaturated ketones.