((2-fluoroallyl)oxy)benzene | 128259-88-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ((2-fluoroallyl)oxy)benzene
• 英文别名: 3-phenoxy-2-fluoro-1-propene；(2-Fluoro-allyloxy)-benzene；2-fluoroprop-2-enoxybenzene
• CAS: 128259-88-1
• 化学式: C₉H₉FO
• 分子量: 152.168
• InChiKey: WTIUYFYDXKMQAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ((2-fluoroallyl)oxy)benzene 在 叠氮基三甲基硅烷 、 Selectfluor 、 三氟乙酸 作用下， 以 水 、 乙腈 为溶剂， 生成 (3-azido-2,2-difluoropropoxy)benzene
  参考文献：
  名称：

  Radical Amido‐ and Azido‐Fluorination of α ‐Fluorostyrene Derivatives: An Innovative Approach Towards β ‐Aryl‐ β , β ‐difluoroamino Motifs

  摘要：

  AbstractAn innovative one‐step synthesis towards β‐aryl‐β,β‐difluorocarbamates and β‐aryl‐β,β‐difluoroazides is presented. The described approach relies on the use of α‐fluorostyrene substrates in a radical addition/fluorination reaction with N‐centered radicals in the presence of Selectfluor®. The best results were obtained for the azidofluorination reaction. The resultant β‐aryl‐β,β‐difluoroazides were further transformed into Nitrogen‐based heterocycles (e. g. pyrrole, triazole, and tetrazole) and in more elaborated azide derivatives.

  DOI：

  10.1002/ejoc.202201165
• 作为产物：
  描述：

  烯丙基苯基醚 在 臭氧 、 二异丙胺 作用下， 反应 34.0h， 生成 ((2-fluoroallyl)oxy)benzene
  参考文献：
  名称：

  2-氟-1-烯烃的新合成

  摘要：

  报道了将PhSeF加到烯烃中以产生β-氟苯基硒化物（）的第一个例子。由末端烯烃制得的β-氟苯基硒化物（）经臭氧处理转化为标题的氟乙烯，而由内烯烃和环状烯烃制得的烯丙基氟化物。该方法提供了以前未报道的2-苄基-2-氟-1-烯烃（例如）的入口。

  DOI：

  10.1016/s0040-4039(00)94406-x

文献信息

• Novel process for the synthesis of 2-fluoro-1-olefins
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0410380A3

  公开（公告）日：1992-04-08

  A process for preparing 2-fluoro-1-olefins or terminal bis-beta-fluoro-olefins which comprises reacting an appropriate allyl or alpha-olefinated starting material with phenylselenyl chloride and silver fluoride, and then reacting the intermediate phenylselenyl fluoride compound with ozone, and further reacting the resulting phenylselenoxide compound with an appropriate amine, to yield the desired fluorinated compounds.

  一种制备2-氟-1-烯或末端双-β-氟-烯的方法，包括将适当的烯丙基或α-烯基起始物与苯硒氯和氟化银反应，然后将中间体苯硒氟化物化合物与臭氧反应，进一步将所得的苯硒氧化物化合物与适当的胺反应，以得到所需的氟化合物。
• [EN] IMPROVED PROCESS FOR THE PREPARATION OF HALO-DIALKOXYBENZENES<br/>[FR] PROCÉDÉ AMÉLIORÉ POUR LA PRÉPARATION D'HALOGÉNO-DIALCOXYBENZÈNES
  申请人：HIKAL LTD

  公开号：WO2011064789A1

  公开（公告）日：2011-06-03

  The invention describes an improved method for producing halo-dialkoxybenzenes of formula (I) such as 1-fluoro-2, 3-dialkoxybenzene as well as 2-fluoro-1, 4-dialkoxybenzene, Formula (I) by reacting commercial 2-fluorophenol is reacted with an allyl halide in N-methylpyrrolidone (NMP) followed by rearranging the resultant 2-fluoroallylphenylether to form 2-allyl-6-fluorophenol and its para isomeric counterpart. This compound mixture is then directly alkylated to form isomeric substituted allyl alkoxybenzenes and subjected to isomerization to form the corresponding propenyl derivatives. All the above four steps are carried out without any workup except one filtration. 6-Fluoro-2-propenyl alkyl phenyl ether is separated from the other isomer by a fractional distillation in good yields. The isomers are oxidized to the corresponding benzaldehydes using oxidants in presence of a halo hydrocarbon solvent. The benzaldehydes is further oxidised with an organic or an inorganic peroxide in a halo hydrocarbon solvent to obtain the corresponding phenols, which is thereby alkylated to form compound of formula (I).

  该发明描述了一种改进的生产卤代二烷氧基苯的方法，其中化学式为(I)，例如1-氟-2,3-二烷氧基苯和2-氟-1,4-二烷氧基苯。通过将商业2-氟苯酚与烯丙基卤化物在N-甲基吡咯烷酮（NMP）中反应，然后重排得到的2-氟烯丙基苯醚形成2-烯丙基-6-氟苯酚及其对位异构体。然后，将这种化合物混合物直接烷基化以形成异构的烯丙基烷氧基苯，并进行异构化以形成相应的丙烯基衍生物。所有以上四个步骤都在除一个过滤之外不进行任何处理。6-氟-2-丙烯基烷基苯醚通过分馏以高收率与其他异构体分离。这些异构体在存在卤代烃溶剂中使用氧化剂氧化为相应的苯甲醛。苯甲醛进一步在卤代烃溶剂中与有机或无机过氧化物氧化以获得相应的酚，然后烷基化以形成化合物的化学式(I)。
• A new synthesis of 2-fluoro-1-olefins
  作者：James R McCarthy、Donald P Matthews、Charlotte L Barney

  DOI：10.1016/s0040-4039(00)94406-x

  日期：1990.1

  The first examples of the addition of PhSeF to olefins to yield β-fluoro phenylselenides () are reported. β-Fluoro phenylselenides () obtained from terminal olefins were converted to the title vinyl fluorides on treatment with ozone, whereas, obtained from internal and cyclic olefins formed allyl fluorides. This method provides an entry to previously unreported 2-benzyl-2-fluoro-1-olefins (e.g. ).

  报道了将PhSeF加到烯烃中以产生β-氟苯基硒化物（）的第一个例子。由末端烯烃制得的β-氟苯基硒化物（）经臭氧处理转化为标题的氟乙烯，而由内烯烃和环状烯烃制得的烯丙基氟化物。该方法提供了以前未报道的2-苄基-2-氟-1-烯烃（例如）的入口。
• Radical Amido‐ and Azido‐Fluorination of <i>α</i> ‐Fluorostyrene Derivatives: An Innovative Approach Towards <i>β</i> ‐Aryl‐ <i>β</i> , <i>β</i> ‐difluoroamino Motifs
  作者：Alphonsine Ngo Ndimba、Émilie Vincent、Julien Brioche

  DOI：10.1002/ejoc.202201165

  日期：2022.11.18

  AbstractAn innovative one‐step synthesis towards β‐aryl‐β,β‐difluorocarbamates and β‐aryl‐β,β‐difluoroazides is presented. The described approach relies on the use of α‐fluorostyrene substrates in a radical addition/fluorination reaction with N‐centered radicals in the presence of Selectfluor®. The best results were obtained for the azidofluorination reaction. The resultant β‐aryl‐β,β‐difluoroazides were further transformed into Nitrogen‐based heterocycles (e. g. pyrrole, triazole, and tetrazole) and in more elaborated azide derivatives.