2,2,2-trifluoro-1-(3-vinylphenyl)ethan-1-one | 1256467-22-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,2-trifluoro-1-(3-vinylphenyl)ethan-1-one
• 英文别名: 2,2,2-Trifluoro-1-(3-vinylphenyl)ethanone；1-(3-ethenylphenyl)-2,2,2-trifluoroethanone
• CAS: 1256467-22-7
• 化学式: C₁₀H₇F₃O
• 分子量: 200.16
• InChiKey: QWKLSBMVJVGSBH-UHFFFAOYSA-N

物化性质

• 沸点：
  233.5±40.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoro-1-(3-vinylphenyl)ethan-1-one 在 pyridine hydrofluoride 、 4-碘甲苯 、 Selectfluor 作用下， 以 氯仿 为溶剂， 反应 22.03h， 以57%的产率得到1-(3-(2,2-difluoroethyl)phenyl)-2,2,2-trifluoroethan-1-one
  参考文献：
  名称：

  Catalytic Geminal Difluorination of Styrenes for the Construction of Fluorine-rich Bioisosteres

  摘要：

  A geminal difluorination of alkenes based on I(I)/I(III) catalysis is disclosed, which is compatible with a range of electronically and substitutionally diverse styrenes (27 examples, up to 89% yield). Employing inexpensive p-Toll as the organocatalyst, turnover is enabled by Selectfluor-mediated oxidation to generate the ArIF2 species in situ. Extension to include alpha-substituted styrenes bearing fluorine-containing groups is disclosed and provides an expansive platform for the generation of fluorine-rich architectures.

  DOI：

  10.1021/acs.orglett.8b03794
• 作为产物：
  描述：

  三氟乙酸乙酯 、 3-溴苯乙烯 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以23%的产率得到2,2,2-trifluoro-1-(3-vinylphenyl)ethan-1-one
  参考文献：
  名称：

  Catalytic Geminal Difluorination of Styrenes for the Construction of Fluorine-rich Bioisosteres

  摘要：

  A geminal difluorination of alkenes based on I(I)/I(III) catalysis is disclosed, which is compatible with a range of electronically and substitutionally diverse styrenes (27 examples, up to 89% yield). Employing inexpensive p-Toll as the organocatalyst, turnover is enabled by Selectfluor-mediated oxidation to generate the ArIF2 species in situ. Extension to include alpha-substituted styrenes bearing fluorine-containing groups is disclosed and provides an expansive platform for the generation of fluorine-rich architectures.

  DOI：

  10.1021/acs.orglett.8b03794

文献信息

• Catalytic <i>Geminal</i> Difluorination of Styrenes for the Construction of Fluorine-rich Bioisosteres
  作者：Felix Scheidt、Jessica Neufeld、Michael Schäfer、Christian Thiehoff、Ryan Gilmour

  DOI：10.1021/acs.orglett.8b03794

  日期：2018.12.21

  A geminal difluorination of alkenes based on I(I)/I(III) catalysis is disclosed, which is compatible with a range of electronically and substitutionally diverse styrenes (27 examples, up to 89% yield). Employing inexpensive p-Toll as the organocatalyst, turnover is enabled by Selectfluor-mediated oxidation to generate the ArIF2 species in situ. Extension to include alpha-substituted styrenes bearing fluorine-containing groups is disclosed and provides an expansive platform for the generation of fluorine-rich architectures.