(1-溴-2-氟-2-丙基)苯 | 59974-27-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (1-溴-2-氟-2-丙基)苯
• 英文名称: (2-bromo-1-fluoro-1-methylethenyl)benzene
• 英文别名: (2-bromo-1-fluoro-1-methyl-ethyl)benzene；1-bromo-2-fluoro-2-phenylpropane；(2-bromo-1-fluoro-1-methylethyl)benzene；1-bromo-2-fluoro-2phenylpropane；2-Phenyl-3-brom-2-fluorpropan；(1-Bromo-2-fluoropropan-2-yl)benzene
• CAS: 59974-27-5
• 化学式: C₉H₁₀BrF
• 分子量: 217.081
• InChiKey: DAYOQOXVQZVQQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1-溴-2-氟-2-丙基)苯 在 氢氧化钾 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.25h， 生成 2-fluoro-2-phenylpropanol
  参考文献：
  名称：

  Synthesis of γ-Fluoro-α, β-unsaturated Carboxylic Esters from Saturated α-Fluoro Aldehydes

  摘要：

  gamma-Fluoro-alpha,beta-unsaturated carboxylic esters 7a, 7b and 7d and 4-fluoro-4-phenylbut-3-enoic ester (8) are obtained by two alternative pathways from 2-fluoro aldehydes 5a-d, either by Horner-Wadsworth-Emmons reaction or by Wittig reaction. The aldehydes 5a-d are prepared by Swern oxidation of the corresponding fluorohydrins 4a-d. These are available from alpha-olefins by bromofluorination, bromine-by-acetate replacement and subsequent hydrolysis.

  DOI：

  10.1002/(sici)1521-3897(200001)342:1<52::aid-prac52>3.0.co;2-h
• 作为产物：
  描述：

  2-苯基-1-丙烯 在 N-溴代丁二酰亚胺(NBS) 、 triethylamine tris-hydrofluoride 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到(1-溴-2-氟-2-丙基)苯
  参考文献：
  名称：

  Triethylamine Tris-hydrofluoride [(C₂H₅)₃N·3HF]: A Highly Versatile Source of Fluoride Ion for the Halofluorination of Alkenes

  摘要：

  N-卤代苏胺/三乙胺三氟化物的组合被提出作为一种方便的试剂，用于烯烃的卤氟化反应。

  DOI：

  10.1055/s-1987-28004

文献信息

• Selective Halofluorination of Alkenes with Tetrabutylphosphonium Dihydrogentrifluoride in Combination with<i>N</i>-Halosuccinimide or 1,3-Dibromo-5,5-dimethylhydantoin
  作者：Yukitaka Uchibori、Masayuki Umeno、Hideharu Seto、Hirosuke Yoshioka

  DOI：10.1246/cl.1993.673

  日期：1993.4

  Alkenes and their functionalized derivatives were readily converted to the corresponding halofluorides with tetrabutylphosphonium dihydrogentrifluoride as combined with N-halosuccinimides or 1,3-dibromo-5,5-dimethylhydantoin in highly regio-, stereo-, and chemoselective manners. In particular, alkenes having a oxirane or primary hydroxyl group also underwent halofluorination selectively in good yields

  烯烃及其官能化衍生物很容易通过四丁基二氢三氟化鏻与 N-卤代琥珀酰亚胺或 1,3-二溴-5,5-二甲基乙内酰脲以高度区域选择性、立体选择性和化学选择性的方式转化为相应的卤代氟化物。特别是，具有环氧乙烷或伯羟基的烯烃也以良好的产率选择性地进行卤氟化。
• Potassium Fluoride-Poly(Hydrogen Fluoride) Salts as Fluorinating Agents for Halofluorination of Alkenes
  作者：Masanori Tamura、Motonari Shibakami、Akira Sekiya

  DOI：10.1055/s-1995-3946

  日期：1995.5

  It was found that potassium fluoride-poly(hydrogen fluoride) salts are useful fluorine sources for halofluorination of alkenes. The reaction proceeded with these salts and N-halosuccinimides or 1,3-dibromo-5,5-dimethylhydantoin in a regio- and stereoselective manner.

  研究发现，氟化钾-聚氢氟化物盐是一种有用的氟源，用于烯烃的卤氟化反应。该反应以这些盐与N-卤代琥珀酰亚胺或1,3-二溴-5,5-二甲基海因在区域选择性和立体选择性条件下进行。
• Selective bromofluorination of alkenes with 1,3-dibromo-5,5-dimethylhydantoin and silicon tetrafluoride
  作者：Makoto Shimizu、Yuko Nakahara、Hirosuke Yoshioka

  DOI：10.1039/c39890001881

  日期：——

  Alkenes have been converted into the corresponding bromofluorides by reaction with 1,3-dibromo-5,5-dimethylhydantoin (DBH) and silicon tetrafluoride in 1,4-dioxane in a highly regio-, stereo-, and chemo-selective manner.

  通过与1,3-二溴-5,5-二甲基乙内酰脲（DBH）和四氟化硅在1,4-二恶烷中以高度区域，立体和化学选择性的方式反应，烯烃已转化为相应的溴氟化物。
• Poly-4-vinylpyridinium Poly(Hydrogen Fluoride): A Solid Hydrogen Fluoride Equivalent Reagent
  作者：George A. Olah、Xing-Ya Li、Qi Wang、G. K. Surya Prakash

  DOI：10.1055/s-1993-25924

  日期：——

  Poly-4-vinylpyridinium poly(hydrogen fluoride) (PVPHF), containing 35-60% hydrogen fluoride by weight, was prepared as a solid hydrogen fluoride equivalent reagent. PVPHF with 60% hydrogen fluoride by weight was found to be a versatile fluorinating agent for the hydrofluorination and bromofluorination of alkenes and alkynes, fluorination of alcohols as well as other fluorination reactions. Low hydrogen fluoride content PVPHF (3 equivalents of hydrogen fluoride to 1 equivalent of 4-vinylpyridine unit) was also found to be an efficient reagent for bromofluorination of alkenes in the presence of 1,3-dibromo-5,5-dimethylhydantoin. Fluorosulfonic acid-modified PVPHF showed enhanced reactivities for the fluorination of secondary alcohols.

  聚-4-乙烯基吡啶聚（氟化氢）（PVPHF）是一种固态氟化氢等效试剂，含有35-60%的氟化氢（按重量计）。发现含有60%氟化氢的PVPHF是一种多功能的氟化试剂，可用于烯烃和炔烃的氟化氢化及溴氟化，醇的氟化以及其他氟化反应。低氟化氢含量的PVPHF（4-乙烯基吡啶单元1当量对应3当量氟化氢）在存在1,3-二溴-5,5-二甲基海因的情况下也被发现是一种有效的烯烃溴氟化试剂。氟磺酸修饰的PVPHF在第二醇氟化反应中显示出增强的反应活性。
• Fluorination process using hydrogen fluoride-containing fluorinating
  申请人：AlliedSignal Inc.

  公开号：US05705717A1

  公开（公告）日：1998-01-06

  Fluorination processes using hydrogen fluoride-containing fluorinating agents that are safely and easily handled, transported, and stored and that also exhibit good reactivity are provided. More particularly, the invention provides processes for producing fluorinated products using fluorinating agents comprising hydrogen fluoride and a carrier that may be an acid salt or a water-soluble polymer.

  提供了使用氢氟酸含氟化剂的氟化过程，这些氟化剂可以安全、轻松地处理、运输和储存，并且还表现出良好的反应性。更具体地，该发明提供了使用包括氢氟酸和可能是酸盐或水溶性聚合物的载体的氟化剂生产氟化产品的过程。

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