1-(2-溴-2-氟乙烯基)-2-甲氧基苯 | 808132-81-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-(2-溴-2-氟乙烯基)-2-甲氧基苯
• 英文名称: 1-(2-bromo-2-fluorovinyl)-2-methoxybenzene
• 英文别名: 1-(2-Bromo-2-fluoroethenyl)-2-methoxybenzene；1-(2-bromo-2-fluoroethenyl)-2-methoxybenzene
• CAS: 808132-81-2
• 化学式: C₉H₈BrFO
• 分子量: 231.064
• InChiKey: JJJSJSVLXRSXQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  2
• 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：

  1-(2-溴-2-氟乙烯基)-2-甲氧基苯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以52%的产率得到(E)-1-(2-bromo-2-fluorovinyl)-2-methoxybenzene
  参考文献：
  名称：

  铜催化杂芳烃的直接C–H氟链烯基化†

  摘要：

  据报道，使用各种宝石-溴氟代烯烃作为亲电试剂，铜催化杂环的直接CH-H氟代烯基化反应。这种有效的方法为相关杂芳基一氟烯烃的经济，低成本和立体控制提供了步骤。据报道，已报道了用于治疗杜兴氏肌营养不良症的生物分子和治疗剂的氟化类似物的合成。

  DOI：

  10.1039/c5ob02213d
• 作为产物：
  描述：

  氟三溴甲烷 、 2-methoxybenzaldehyde hydrazone 在 乙二胺 、 copper(l) chloride 作用下， 以 乙醇 为溶剂， 生成 1-(2-溴-2-氟乙烯基)-2-甲氧基苯
  参考文献：
  名称：

  Synthesis and Diels–Alder reactions of α-fluoro- and α-trifluoromethylacrylonitriles

  摘要：

  A novel synthetic method for the preparation of alpha-fluoro- and the still unknown alpha-trifluoromethylacrylonitriles is elaborated. The reaction of alpha-fluorovinylbromides and alpha-trifluoromethylvinylbromides with CuCN leads to the title compounds in good to high yields. While the alpha-fluoroacrylonitriles were isolated as mixture of Z/E-isomers, the alpha-trifluoromethylacrylonitriles were obtained as pure Z-isomers. The alpha-trifluoromethylacrylonitriles are shown to be excellent dienophiles for Diels-Alder reactions. (c) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2007.02.014

文献信息

• New synthetic approach to α-fluoro-β-arylvinyl sulfones and their application in Diels–Alder reactions
  作者：Aleksey V. Shastin、Valentine G. Nenajdenko、Vasiliy M. Muzalevskiy、Elizabeth S. Balenkova、Roland Fröhlich、Günter Haufe

  DOI：10.1016/j.tet.2008.07.097

  日期：2008.10

  obtained as the major products. From these cycloadducts, as a proof of principle, p-toluenesulfinic acid was eliminated to give 2-fluoro-3-(4-nitrophenyl)norbornadiene, the formal [4+2]-cycloadduct of cyclopentadiene and 1-fluoro-2-(4-nitrophenyl)acetylene, or the corresponding diphenylisobenzofuran cycloadducts, respectively. This reaction was not successful when other β-hydrogen atoms are accessible for

  阐述了通往α-氟-β-芳基乙烯基砜的新途径。β-溴-β-氟苯乙烯与4-甲基苯基亚磺酸钠的反应以最大的94：6立体选择性和72-90％的产率进行。发现形成的α-氟-β-芳基乙烯基砜是与简单的1,3-二烯进行Diels-Alder反应的良好的亲二烯体。从相应的（É）构型亲二烯体和环戊二烯，cycloadducts轴承氟取代基在外型-位被主要形成，同时与diphenylisobenzofuran的产品内的氟的-orientation作为主要产物而获得。从这些环加合物中，作为原理证明，p除去-甲苯亚磺酸，得到2-氟-3-（4-硝基苯基）降冰片二烯，环戊二烯和1-氟-2-（4-硝基苯基）乙炔的正式[4 + 2]-环加合物或相应的二苯基异苯并呋喃环加合物， 分别。当其他β-氢原子可被消除时，该反应并不成功。
• Palladium-Catalyzed Cross-Coupling of Gem-Bromofluoroalkenes with Alkylboronic Acids for the Synthesis of Alkylated Monofluoroalkenes
  作者：Laëtitia Chausset-Boissarie、Nicolas Cheval、Christian Rolando

  DOI：10.3390/molecules25235532

  日期：——

  versatile fluorinated synthons in organic synthesis, medicinal chemistry and materials science. In light of the importance of alkyl-substituted monofluoroalkenes efficient synthesis of these moieties still represents a synthetic challenge. Herein, we described a mild and efficient methodology to obtain monofluoroalkenes through a stereospecific palladium-catalyzed alkylation of gem-bromofluoroalkenes with

  单氟烯烃是有机合成、药物化学和材料科学中的多功能氟化合成子。鉴于烷基取代的单氟烯烃的重要性，这些部分的有效合成仍然是合成挑战。在此，我们描述了一种温和而有效的方法，通过在温和条件下通过立体有择钯催化的溴氟烯烃与伯和应变仲烷基硼酸的烷基化来获得单氟烯烃。这种新颖的策略可以高产率地获得各种功能化的三取代和四取代的单氟烯烃，具有良好的官能团耐受性，独立于嵴溴氟烯烃的几何形状。
• Organophotocatalysis Enables the Synthesis of <i>gem</i>-Fluorophosphonate Alkenes
  作者：Solène Morand、William Lecroq、Philippe Jubault、Sami Lakhdar、Jean-Philippe Bouillon、Samuel Couve-Bonnaire

  DOI：10.1021/acs.orglett.2c03366

  日期：2022.11.18
• Copper-catalyzed direct C–H fluoroalkenylation of heteroarenes
  作者：Kevin Rousée、Cédric Schneider、Jean-Philippe Bouillon、Vincent Levacher、Christophe Hoarau、Samuel Couve-Bonnaire、Xavier Pannecoucke

  DOI：10.1039/c5ob02213d

  日期：——

  Copper-catalyzed direct C–H fluoroalkenylation of heterocycles using various gem-bromofluoroalkenes as electrophiles is reported. This efficient method offers step-economical, low-cost and stereocontrolled access to relevant heteroarylated monofluoroalkenes. The synthesis of fluorinated analogues of biomolecules and therapeutic agents for the treatment of Duchenne muscular dystrophy as application

  据报道，使用各种宝石-溴氟代烯烃作为亲电试剂，铜催化杂环的直接CH-H氟代烯基化反应。这种有效的方法为相关杂芳基一氟烯烃的经济，低成本和立体控制提供了步骤。据报道，已报道了用于治疗杜兴氏肌营养不良症的生物分子和治疗剂的氟化类似物的合成。
• Synthesis and Diels–Alder reactions of α-fluoro- and α-trifluoromethylacrylonitriles
  作者：Valentine G. Nenajdenko、Vasiliy M. Muzalevskiy、Aleksey V. Shastin、Elizabeth S. Balenkova、Günter Haufe

  DOI：10.1016/j.jfluchem.2007.02.014

  日期：2007.7

  A novel synthetic method for the preparation of alpha-fluoro- and the still unknown alpha-trifluoromethylacrylonitriles is elaborated. The reaction of alpha-fluorovinylbromides and alpha-trifluoromethylvinylbromides with CuCN leads to the title compounds in good to high yields. While the alpha-fluoroacrylonitriles were isolated as mixture of Z/E-isomers, the alpha-trifluoromethylacrylonitriles were obtained as pure Z-isomers. The alpha-trifluoromethylacrylonitriles are shown to be excellent dienophiles for Diels-Alder reactions. (c) 2007 Elsevier B.V. All rights reserved.