(E)-Perfluorobut-1-enyl phenyl ketone | 151961-14-7

• 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)-Perfluorobut-1-enyl phenyl ketone
• 英文别名: (E)-2,3,4,4,5,5,5-heptafluoro-1-phenylpent-2-en-1-one
• CAS: 151961-14-7
• 化学式: C₁₁H₅F₇O
• 分子量: 286.149
• InChiKey: ZBNJVQQRQFRANH-VQHVLOKHSA-N

物化性质

• 沸点：
  210.2±40.0 °C(predicted)
• 密度：
  1.417±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  (E)-Perfluorobut-1-enyl phenyl ketone 在 氢氧化钾 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 120.0h， 生成 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：

  2,2,3,3,4,4,5,5,5-Nonafluoro-1-phenyl-1-trimethylsilylpentan-1-ol 在 potassium fluoride 、 silica gel 作用下， 生成 (E)-Perfluorobut-1-enyl phenyl ketone
  参考文献：
  名称：

  Mixed organofluorine-organosilicon chemistry. 3. A highly efficient and convenient synthesis of aryl perfluoroalk-1-enyl ketones from perfluoroalkyl iodides and aroylsilanes

  摘要：

  A one-pot procedure is described to synthesize aryl perfluoroalkenyl ketones with high yields from perfluoroalkyl iodides and aroylsilanes. It consists of conversion of the iodide to the perfluoroorganomagnesium bromide followed by reaction with the aroylsilane, in ether, at low temperatures (-45-degrees-C). Warming to room temperature and addition of triethylamine accelerate the process leading quantitatively to the enones, which can be isolated in the pure E-configuration. The mechanism of this synthesis, involving a Brook rearrangement, is discussed. An alternative procedure is proposed to synthesize the same enones, with equivalent efficiency, from 1-aryl-1-(trimethylsilyl)perfluoroalkan-1-ols.

  DOI：

  10.1021/jo00076a028

文献信息

• 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。
• Intra–Intermolecular Criss-cross Cycloaddition of Nonsymmetrical Allenylazines with Fluorinated Enones as an Initial Step in the Synthesis of4H-Pyrrolo[1,2-b]pyrazoles
  作者：Stanislav Man、Marek Nečas、Jean-Philippe Bouillon、Charles Portella、Milan Potáček

  DOI：10.1002/ejoc.200600175

  日期：2006.8

  Nonsymmetrical allenylazines undergo in boiling xylene intramolecular cycloaddition via formation of an unstable 1,3-dipole, which reacts with an added dipolarophile. In this paper we pay attention to the first intra-intermolecular criss-cross cycloaddition with a fluorinated enone. Although the expected products with three fused heterocycles were not isolated, new bicyclic products were found and

  不对称的烯丙嗪通过形成不稳定的 1,3-偶极子在沸腾的二甲苯分子内环加成中进行，该 1,3-偶极子与添加的亲偶极体反应。在本文中，我们关注了第一次与氟化烯酮的分子间交叉环加成反应。虽然没有分离出具有三个稠合杂环的预期产物，但发现并表征了新的双环产物。这些化合物是通过与氟原子迁移和氟化氢消除相关的自发转化形成的。讨论了反应机制来解释这些新杂环的形成。
• 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.
• Mixed organofluorine-organosilicon chemistry. 3. A highly efficient and convenient synthesis of aryl perfluoroalk-1-enyl ketones from perfluoroalkyl iodides and aroylsilanes
  作者：Boniface Dondy、Charles Portella

  DOI：10.1021/jo00076a028

  日期：1993.11

  A one-pot procedure is described to synthesize aryl perfluoroalkenyl ketones with high yields from perfluoroalkyl iodides and aroylsilanes. It consists of conversion of the iodide to the perfluoroorganomagnesium bromide followed by reaction with the aroylsilane, in ether, at low temperatures (-45-degrees-C). Warming to room temperature and addition of triethylamine accelerate the process leading quantitatively to the enones, which can be isolated in the pure E-configuration. The mechanism of this synthesis, involving a Brook rearrangement, is discussed. An alternative procedure is proposed to synthesize the same enones, with equivalent efficiency, from 1-aryl-1-(trimethylsilyl)perfluoroalkan-1-ols.