(1,6-difluoro-3,4-dimethyl-6-pentafluoroethylcyclohex-3-enyl)-phenone | 440650-46-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1,6-difluoro-3,4-dimethyl-6-pentafluoroethylcyclohex-3-enyl)-phenone
• 英文别名: [1,6-Difluoro-3,4-dimethyl-6-(1,1,2,2,2-pentafluoroethyl)cyclohex-3-en-1-yl]-phenylmethanone；[1,6-difluoro-3,4-dimethyl-6-(1,1,2,2,2-pentafluoroethyl)cyclohex-3-en-1-yl]-phenylmethanone
• CAS: 440650-46-4
• 化学式: C₁₇H₁₅F₇O
• 分子量: 368.294
• InChiKey: JBJUEUAUBJQQJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1,6-difluoro-3,4-dimethyl-6-pentafluoroethylcyclohex-3-enyl)-phenone 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以75%的产率得到1-(4',5'-dimethyl-2'-pentafluoroethyl)phenyl-phenone
  参考文献：
  名称：

  Synthesis of ortho-perfluoroalkyl phenones from hemifluorinated enones as key building blocks

  摘要：

  The title compounds are prepared by cycloaddition of perfluoroalkenyl ketones and 1,3-dienes, with a subsequent aromatization by basic dehydrofluorination. The perfluoroalkenyl ketones were prepared by the reaction of perfluoroorganometallic reagents with acylsilanes. The transformation may be performed more efficiently in a simplified process without purification of the intermediate cycloadducts. The overall methodology is an interesting entry to ortho-perfluoroalkyl phenones with the possibility to vary the substitution at the acyl and on the ring moiety. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.07.004
• 作为产物：
  描述：

  三甲基硅基苯甲酮 以 乙醚 、 甲苯 为溶剂， 反应 96.0h， 生成 (1,6-difluoro-3,4-dimethyl-6-pentafluoroethylcyclohex-3-enyl)-phenone
  参考文献：
  名称：

  Diels–Alder反应中全氟链烯酮的亲二亲反应性

  摘要：

  通过全氟有机金属试剂与酰基硅烷反应制得的全氟烯基酮，在与各种二烯进行的狄尔斯-阿尔德反应中，是多才多艺的亲二烯体。

  DOI：

  10.1016/s0040-4039(02)00107-7

文献信息

• Synthesis of ortho-perfluoroalkyl phenones from hemifluorinated enones as key building blocks
  作者：Frédéric Chanteau、Richard Plantier-Royon、Günter Haufe、Charles Portella

  DOI：10.1016/j.tet.2006.07.004

  日期：2006.9

  The title compounds are prepared by cycloaddition of perfluoroalkenyl ketones and 1,3-dienes, with a subsequent aromatization by basic dehydrofluorination. The perfluoroalkenyl ketones were prepared by the reaction of perfluoroorganometallic reagents with acylsilanes. The transformation may be performed more efficiently in a simplified process without purification of the intermediate cycloadducts. The overall methodology is an interesting entry to ortho-perfluoroalkyl phenones with the possibility to vary the substitution at the acyl and on the ring moiety. (c) 2006 Elsevier Ltd. All rights reserved.
• Dienophilic reactivity of perfluoroalkenyl ketones in Diels–Alder reactions
  作者：Frédéric Chanteau、Michael Essers、Richard Plantier-Royon、Günter Haufe、Charles Portella

  DOI：10.1016/s0040-4039(02)00107-7

  日期：2002.2

  Perfluoroalkenyl ketones, obtained by reaction of perfluoroorganometallic reagents with acylsilanes, are shown to be versatile dienophiles in Diels–Alder reactions with various dienes.

  通过全氟有机金属试剂与酰基硅烷反应制得的全氟烯基酮，在与各种二烯进行的狄尔斯-阿尔德反应中，是多才多艺的亲二烯体。