(E)-4-chloro-4,4-difluoro-1-phenyl-2-buten-1-one | 355137-35-8

• 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: (E)-4-chloro-4,4-difluoro-1-phenyl-2-buten-1-one
• 英文别名: (E)-4-chloro-4,4-difluoro-1-phenylbut-2-en-1-one
• CAS: 355137-35-8
• 化学式: C₁₀H₇ClF₂O
• 分子量: 216.615
• InChiKey: PQOWKRWCRVNVTR-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  3
• 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：
  3

反应信息

• 作为反应物：
  描述：

  反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 、 (E)-4-chloro-4,4-difluoro-1-phenyl-2-buten-1-one 以 二氯甲烷 为溶剂， 反应 19.0h， 以91%的产率得到[(1R,6S)-6-(Chloro-difluoro-methyl)-2-methoxy-4-trimethylsilanyloxy-cyclohex-3-enyl]-phenyl-methanone
  参考文献：
  名称：

  Synthetic Applications of α-Fluoroalkylated Enones. 1. Use as Dienophiles in Diels−Alder Cycloadditions

  摘要：

  beta-Fluoroalkylated enones are efficient dienophiles in Diels-Alder cycloadditions to prepare various fluorinated cylic compounds. However, the presence of the fluoroalkyl moiety modifies the reactivity and the selectivity of these cycloadditions.

  DOI：

  10.1021/jo052567+
• 作为产物：
  描述：

  苯乙酮 、 1-(4-benzylpiperazino)-2-chloro-2,2-difluoroethyl trimethylsilyl ether 在 三氟化硼乙醚 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以70%的产率得到(E)-4-chloro-4,4-difluoro-1-phenyl-2-buten-1-one
  参考文献：
  名称：

  Reactivity of Stable Trifluoroacetaldehyde Hemiaminals. 1. An Unexpected Reaction with Enolizable Carbonyl Compounds

  摘要：

  In the presence of enolizable carbonyl compounds, hemiaminals of fluoral and related polyfluoro-aldehydes behave as equivalents of fluoroalkyl iminium compounds and provide beta -polyfluoroalkyl beta -dialkylamino ketones, which are easily transformed, under acidic conditions, into beta -polyfluoroalkylenones.

  DOI：

  10.1021/jo015587u

文献信息

• Synthetic Applications of α-Fluoroalkylated Enones. 1. Use as Dienophiles in Diels−Alder Cycloadditions
  作者：Julia Leuger、Gaëlle Blond、Roland Fröhlich、Thierry Billard、Günter Haufe、Bernard R. Langlois

  DOI：10.1021/jo052567+

  日期：2006.3.31

  beta-Fluoroalkylated enones are efficient dienophiles in Diels-Alder cycloadditions to prepare various fluorinated cylic compounds. However, the presence of the fluoroalkyl moiety modifies the reactivity and the selectivity of these cycloadditions.
• Reactivity of Stable Trifluoroacetaldehyde Hemiaminals. 1. An Unexpected Reaction with Enolizable Carbonyl Compounds
  作者：Gaëlle Blond、Thierry Billard、Bernard R. Langlois

  DOI：10.1021/jo015587u

  日期：2001.7.1

  In the presence of enolizable carbonyl compounds, hemiaminals of fluoral and related polyfluoro-aldehydes behave as equivalents of fluoroalkyl iminium compounds and provide beta -polyfluoroalkyl beta -dialkylamino ketones, which are easily transformed, under acidic conditions, into beta -polyfluoroalkylenones.