2,2-difluoro-4,5-dimethyl-1-(naphthalen-2-yl)hex-4-en-1-one | 1338328-51-0

• 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: 2,2-difluoro-4,5-dimethyl-1-(naphthalen-2-yl)hex-4-en-1-one
• 英文别名: 2,2-Difluoro-4,5-dimethyl-1-naphthalen-2-ylhex-4-en-1-one
• CAS: 1338328-51-0
• 化学式: C₁₈H₁₈F₂O
• 分子量: 288.337
• InChiKey: FOACZJZKQGZGIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,2,4,4,4-pentafluoro-3,3-dihydroxy-1-(naphthalen-2-yl)butan-1-one 在 碘 、 铜 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 15.5h， 生成 2,2-difluoro-4,5-dimethyl-1-(naphthalen-2-yl)hex-4-en-1-one 、
  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.