(E)-1-bromo-4-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-octen-1-yl)benzene | 340157-83-7

• 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)-1-bromo-4-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-octen-1-yl)benzene
• 英文别名: 1-(4'-bromophenyl)-3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene；4-bromo-1-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene)benzene；1-bromo-4-[(E)-3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-enyl]benzene
• CAS: 340157-83-7
• 化学式: C₁₄H₆BrF₁₃
• 分子量: 501.085
• InChiKey: JEEHGUPEWILKFO-AATRIKPKSA-N

物化性质

• 沸点：
  293.3±40.0 °C(Predicted)
• 密度：
  1.668±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (E)-1-bromo-4-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-octen-1-yl)benzene 在 Rh on carbon 氢气 作用下， 以 乙酸乙酯 为溶剂， 以92%的产率得到1-溴-4-(1H,1H,2H,2H-全氟辛基)苯
  参考文献：
  名称：

  A general method to fluorous ponytail-substituted aromatics

  摘要：

  Palladium-catalyzed olefination of aryl halides led to a variety of fluorous ponytail-substituted, functionalized aryl compounds with good to excellent yields. The same chemistry was also applied to the synthesis of binaphathols bearing fluorinated ponytails. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00714-6
• 作为产物：
  描述：

  对溴碘苯 、 1H,1H,2H-全氟-1-辛烯 在 palladium diacetate 四丁基溴化铵 、 sodium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以91%的产率得到(E)-1-bromo-4-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-octen-1-yl)benzene
  参考文献：
  名称：

  A general method to fluorous ponytail-substituted aromatics

  摘要：

  Palladium-catalyzed olefination of aryl halides led to a variety of fluorous ponytail-substituted, functionalized aryl compounds with good to excellent yields. The same chemistry was also applied to the synthesis of binaphathols bearing fluorinated ponytails. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00714-6

文献信息

• Copper-Catalyzed Decarboxylative Difluoroalkylation and Perfluoroalkylation of α,β-Unsaturated Carboxylic Acids
  作者：Yin-Long Lai、Dian-Zhao Lin、Jing-Mei Huang

  DOI：10.1021/acs.joc.6b02613

  日期：2017.1.6

  Copper-catalyzed decarboxylative difluoroalkylation and perfluoroalkylation of α,β-unsaturated carboxylic acids is described. Promoted by dialkyl phosphite, this novel reaction affords fluoroalkylated motifs with excellent stereoselectivity and broad substrate scope under mild reaction conditions from readily available fluoroalkyl iodides and bromides. Preliminary mechanism study suggests that radical

  描述了铜催化的α，β-不饱和羧酸的脱羧二氟烷基化和全氟烷基化。在亚磷酸二烷基酯的促进下，这种新颖的反应在温和的反应条件下，由易得的氟代烷基碘和溴化物提供了具有出色的立体选择性和广泛的底物范围的氟代烷基化基序。初步的机理研究表明自由基途径参与了催化循环，亚磷酸二烷基酯在该反应中起着不可或缺的作用。
• Copper-catalyzed fluoroalkylation of alkynes, and alkynyl & vinyl carboxylic acids with fluoroalkyl halides
  作者：Jing-Jing Ma、Wen-Bin Yi

  DOI：10.1039/c7ob00641a

  日期：——

  Copper-catalyzed fluoroalkylation of alkynes and alkynyl carboxylic acids has been achieved with high functional-group tolerance and excellent regio- and stereoselectivities. A variety of fluoroalkyl halides including ethyl bromodifluoroacetate can be employed. Additionally, an unprecedented decarboxylative fluoroalkylation of α, β-unsaturated carboxylic acids has been achieved via a radical pathway.

  炔烃和炔基羧酸的铜催化氟代烷基化反应具有很高的官能团耐受性和优异的区域选择性和立体选择性。可以使用多种氟代烷基卤化物，包括溴二氟乙酸乙酯。另外，已经通过自由基途径实现了前所未有的α，β-不饱和羧酸的脱羧氟烷基化。
• Efficient Access to Perfluoroalkylated Aryl Compounds by Heck Reaction
  作者：Sylvain Darses、Mathieu Pucheault、Jean-Pierre Genêt

  DOI：10.1002/1099-0690(200103)2001:6<1121::aid-ejoc1121>3.0.co;2-3

  日期：2001.3

  been achieved by Heck reaction between perfluoroalkenes and arenediazonium salts, catalysed by palladium acetate. Subsequent transition metal catalysed hydrogenation of the double bond afforded a large variety of aromatic compounds bearing an affinity for fluorous solvents. Formation of perfluoroalkylated phosphane ligands and their use in palladium-catalysed coupling between potassium trifluoro(vinyl)borates

  通过全氟烯烃和芳烃重氮盐之间的 Heck 反应，在乙酸钯的催化下，将全氟化尾有效地引入到芳环上。随后的过渡金属催化的双键氢化提供了多种对氟溶剂具有亲和力的芳香族化合物。还描述了全氟烷基化磷烷配体的形成及其在三氟（乙烯基）硼酸钾和重氮盐之间的钯催化偶联中的应用，使催化系统易于分离和回收。
• An efficient synthesis of perfluoroalkenylated aryl compounds via Pincer-Pd catalyzed Heck couplings
  作者：Jie Feng、Chun Cai

  DOI：10.1016/j.jfluchem.2012.12.009

  日期：2013.2

  Heck couplings of aryl halides with fluoroalkyl-substituted ethylenes catalyzed by Pincer Palladium complex were described. A variety of fluorous ponytail-substituted aromatics were obtained with moderate to excellent yields. Moreover, the catalyst can be easily separated from the reaction mixture by F-SPE technique and reused three times without significant loss of activity.

  描述了由Pincher钯配合物催化的芳基卤化物与氟代烷基取代的乙烯的Heck偶联。中度得到以优异的产率的各种氟马尾取代芳烃。此外，通过F-SPE技术可以容易地将催化剂从反应混合物中分离出来并重复使用三遍，而不会显着降低活性。
• A general method to fluorous ponytail-substituted aromatics
  作者：Weiping Chen、Lijin Xu、Jianliang Xiao

  DOI：10.1016/s0040-4039(01)00714-6

  日期：2001.6

  Palladium-catalyzed olefination of aryl halides led to a variety of fluorous ponytail-substituted, functionalized aryl compounds with good to excellent yields. The same chemistry was also applied to the synthesis of binaphathols bearing fluorinated ponytails. (C) 2001 Elsevier Science Ltd. All rights reserved.