(E)-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-1-decen-1-yl)benzene | 82497-73-2

• 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)-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-1-decen-1-yl)benzene
• 英文别名: (E)-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodec-1-en-1-yl)benzene；(E)-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecen-1-yl)benzene；(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodec-1-enyl)benzene；3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-1-phenyldec-1-ene；(E)-1-phenyl-2-(perfluorooctyl)ethylene；trans-β-(perflouroalkyl)styrene；[(E)-3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodec-1-enyl]benzene
• CAS: 82497-73-2；106873-72-7；106873-83-0
• 化学式: C₁₆H₇F₁₇
• 分子量: 522.204
• InChiKey: AAIMQXYZLLFHQC-VOTSOKGWSA-N

物化性质

• 沸点：
  275.5±40.0 °C(Predicted)
• 密度：
  1.540±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  1,3-bis(1-iodo-3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecan-1-yl)tetramethyldisiloxane 在 三氟化硼乙醚 、 四丁基氟化铵 、 palladium diacetate 、 二乙胺 作用下， 以 三氟甲苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 84.0h， 生成 (E)-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-1-decen-1-yl)benzene
  参考文献：
  名称：

  Hiyama coupling reaction of fluorous alkenyl-fluorosilanes: Scope and mechanistic considerations

  摘要：

  Novel fluorous alkenyl-fluorosilanes (CnF2n+1CH=CHSiMe2F; n = 4, 6, 8; 5a-c) were synthetized in a three step procedure from perfluoroalkyliodides and dimethylvinylchlorosilane. They were first reacted with iodobenzene at room temperature in Hiyama coupling reaction (DMF, Pd(OAc)(2), TBAF, 72 h) to afford the appropriate omega-perfluoroalkyl-styrenes (CnF2n+1CH=CHC6H5, n = 4, 6, 8): then the reactivity of 5a with monosubstituted iodobenzenes was studied. The coupling reaction of Sa with o-substituted iodobenzenes usually failed, while that of with the m- and p-substituted ones gave fluorous styrenes [m- or p-(C4F9CH=CH)C6H4X], independently of the electronic effect of their substituent (X = Br, CF3, CH3, OCH3). These volatile products can easily be isolated by steam-distilltaion and purified further by distillation. The mechanism of the above coupling reactions was a pure Hiyama type involving fluoride-ion induced transmetallation without any Heck type contribution, since no coupling product of C6F13CH=CH2 and C6H5I was observed in blank control experiments using similar conditions (DMF, TBAF, Pd(OAc)(2), 72 h, 25 degrees C). (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2012.03.007

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。
• Visible-light Promoted Atom Transfer Radical Addition−Elimination (ATRE) Reaction for the Synthesis of Fluoroalkylated Alkenes Using DMA as Electron-donor
  作者：Wen-Wen Xu、Le Wang、Ting Mao、Jiwei Gu、Xiao-Fei Li、Chun-Yang He

  DOI：10.3390/molecules25030508

  日期：——

  Here, we describe a mild, catalyst-free and operationally-simple strategy for the direct fluoroalkylation of olefins driven by the photochemical activity of an electron donor−acceptor (EDA) complex between DMA and fluoroalkyl iodides. The significant advantages of this photochemical transformation are high efficiency, excellent functional group tolerance, and synthetic simplicity, thus providing a

  在这里，我们描述了一种温和、无催化剂且操作简单的策略，用于由 DMA 和氟烷基碘化物之间的电子供体 - 受体（EDA）复合物的光化学活性驱动的烯烃直接氟烷基化。这种光化学转化的显着优势是高效、优异的官能团耐受性和合成简单性，从而为进一步应用于制药和生命科学提供了一条捷径。
• 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。
• Fluoroalkenylation of boronic acids <i>via</i> an oxidative Heck reaction
  作者：Da Seul Lee、Eun Jin Cho

  DOI：10.1039/c9ob00332k

  日期：——

  A fluoroalkenylation of boronic acids with fluoroalkyl alkenes has been developed. The Pd-catalyzed oxidative Heck coupling reaction proceeds under an oxygen atmosphere at room temperature, in the absence of a base and/or a ligand, showing excellent practicality of the process. This simple transformation is highly stereoselective to provide only E-isomers. In addition to the general approach using

  已经开发了用氟代烷基烯烃对硼酸的氟代烯基化。Pd催化的氧化Heck偶联反应是在室温下在氧气气氛下，在没有碱和/或配体的情况下进行的，显示了该方法的极好的实用性。这种简单的转化是高度立体选择性的，仅提供E-异构体。除了将烯烃与官能化的氟代烷基试剂一起使用的一般方法外，该方法还通过将芳香族体系转移至缺电子的氟代烷基烯烃上，提供了一种有效的替代方法来生产有价值的有机氟。
• 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。