1-(benzothiophen-3-yl)-2-bromo-2,2-difluoroethanone | 1338328-39-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 1-(benzothiophen-3-yl)-2-bromo-2,2-difluoroethanone
• 英文别名: 1-(Benzo[b]thiophen-3-yl)-2-bromo-2,2-difluoroethanone；1-(1-benzothiophen-3-yl)-2-bromo-2,2-difluoroethanone
• CAS: 1338328-39-4
• 化学式: C₁₀H₅BrF₂OS
• 分子量: 291.116
• InChiKey: ANVIMBIBGMJOHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(benzothiophen-3-yl)-2,2,4,4,4-pentafluoro-3,3-dihydroxybutan-1-one 在 Selectfluor 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到1-(benzothiophen-3-yl)-2-bromo-2,2-difluoroethanone
  参考文献：
  名称：

  Synthesis of α-Halo-α,α-difluoromethyl Ketones by a Trifluoroacetate Release/Halogenation Protocol

  摘要：

  Three series of alpha-halo-alpha,alpha-difluoromethyl ketones are prepared from highly alpha-fluorinated gem-dials by exploiting the facile release of trifluoroacetate, followed by immediate trapping of the liberated alpha,alpha-difluoroenolate with an electrophilic chlorine, bromine, or iodine source. The products are typically isolated in good yields, even in the case of sensitive, alpha-iodo-alpha,alpha-difluoromethyl ketones. Also, we demonstrate that an alpha-iodo-alpha,alpha-difluoromethyl ketone will participate in a copper-promoted reaction to forge a new carbon-carbon bond.

  DOI：

  10.1021/jo2017179

文献信息

• Synthesis of α-Halo-α,α-difluoromethyl Ketones by a Trifluoroacetate Release/Halogenation Protocol
  作者：Jinu P. John、David A. Colby

  DOI：10.1021/jo2017179

  日期：2011.11.4

  Three series of alpha-halo-alpha,alpha-difluoromethyl ketones are prepared from highly alpha-fluorinated gem-dials by exploiting the facile release of trifluoroacetate, followed by immediate trapping of the liberated alpha,alpha-difluoroenolate with an electrophilic chlorine, bromine, or iodine source. The products are typically isolated in good yields, even in the case of sensitive, alpha-iodo-alpha,alpha-difluoromethyl ketones. Also, we demonstrate that an alpha-iodo-alpha,alpha-difluoromethyl ketone will participate in a copper-promoted reaction to forge a new carbon-carbon bond.