[(1E)-3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-iodo-1-octen-1-yl]benzene | 125081-20-1

• 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: [(1E)-3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-iodo-1-octen-1-yl]benzene
• 英文别名: (E)-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-iodooct-1-enyl)benzene；1-phenyl-1-iodo-2-perfluorohexyl ethene；[(E)-3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-iodooct-1-enyl]benzene
• CAS: 125081-20-1
• 化学式: C₁₄H₆F₁₃I
• 分子量: 548.085
• InChiKey: KYNCXBOOGXBAEN-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 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：

  [(1E)-3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-iodo-1-octen-1-yl]benzene 在 palladium on activated charcoal 正丁基锂 、 氢气 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 20.0~70.0 ℃ 、100.0 kPa 条件下， 反应 24.0h， 生成 (1-Benzyl-2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoro-heptyl)-dihexyl-amine
  参考文献：
  名称：

  An easy three step synthesis of perfluoroalkylated amphetamines

  摘要：

  A general synthesis of perfluoroalkylated amphetamines is presented. Initially, 1-aryl-1-iodo-2-(perfluoroalkyl)ethylenes are prepared by radical addition of perfluoroalkyl iodides to arylacetylenes. Key step of the reaction sequence is the following dehydroiodination in the presence of n-BuLi to give 1-perfluoroalkyl-2-arylacetylenes in situ, which are reacted with secondary amines to produce perfluoroalkylated enamines in a new one pot procedure. Final hydrogenation yields the desired products in good yields. By using N,N-dibenzylamine or N-benzylamines the corresponding primary and secondary perfluoroalkylated amines are easily available. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.08.080
• 作为产物：
  描述：

  全氟己基碘烷 、 苯乙炔 在 caesium carbonate 、 iron(II) bromide 作用下， 以 1,4-二氧六环 为溶剂， 以67%的产率得到[(1E)-3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-iodo-1-octen-1-yl]benzene
  参考文献：
  名称：

  铁催化的1,2-全氟烷基碘化物加成至炔烃和烯烃

  摘要：

  已经开发出铁催化用于将全氟烷基碘分子间1,2加成到炔烃和烯烃中。催化作用具有广泛的底物范围和较高的官能团耐受性。可以使用包括CF 3 I在内的各种全氟烷基碘。生成的全氟烷基化烷基碘和链烯基碘可以通过交叉偶联反应进一步官能化。该方法提供了对全氟烷基化有机分子的直接且简化的访问。

  DOI：

  10.1002/anie.201402511

文献信息

• Triethylborane-induced stereoselective radical addition of perfluoroalkyl iodides to acetylenes
  作者：Yoshihiro Takeyama、Yoshifumi Ichinose、Koichiro Oshima、Kiitiro Utimoto

  DOI：10.1016/s0040-4039(00)99190-1

  日期：——

  acetylenes bearing a variety of substituents with perfluoroalkyl iodides in the presence of a catalytic amount of triethylborane provides the corresponding perfluoroalkenes in good to excellent yields. The addition of perfluoroalkyl iodides to olefins is also described.

  在催化量的三乙基硼烷的存在下，用全氟烷基碘处理带有各种取代基的末端或内部乙炔，可以以良好或极好的收率得到相应的全氟烯烃。还描述了将全氟烷基碘化物加到烯烃中。
• 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。
• Visible Light-Induced Radical Iodoperfluoroalkylation of Unactivated Olefins Cooperatively Catalyzed by Enamines and Amines
  作者：Tomoko Yajima、Mao Murase、Yu Ofuji

  DOI：10.1002/ejoc.201901896

  日期：2020.7.7

  Metal‐free visible light‐induced ATRA of perfluoroalkyl iodide was performed. The reaction is effective for various perfluoroalkyl iodide and unactivated alkenes and alkynes and proceeded smoothly with 1 mol‐% aldehyde and amine.

  进行了无金属可见光诱导的全氟烷基碘的ATRA。该反应对各种全氟烷基碘和未活化的烯烃和炔烃有效，并且在1 mol％的醛和胺的条件下可以顺利进行。
• Stereoselective cobalt-catalyzed halofluoroalkylation of alkynes
  作者：Guojiao Wu、Axel Jacobi von Wangelin

  DOI：10.1039/c7sc04916a

  日期：——

  Stereoselective additions of highly functionalized reagents to available unsaturated hydrocarbons are an attractive synthetic tool due to their high atom economy, modularity, and rapid generation of complexity. We report efficient cobalt-catalyzed (E)-halofluoroalkylations of alkynes/alkenes that enable the construction of densely functionalized, stereodefined fluorinated hydrocarbons. The mild conditions

  将高度功能化的试剂立体选择性添加到可用的不饱和烃中是一种有吸引力的合成工具，因为它们具有高原子经济性、模块化和快速产生复杂性。我们报道了炔烃/烯烃的高效钴催化 （E）-卤氟烷基化反应，能够构建致密官能化、定型的氟化烃。温和的条件（2 mol% 货号，20 °C，丙酮/水，3 小时）可耐受各种官能团，即卤化物、醇、醛、腈、酯和杂芳烃。该反应是高度立体选择性钴催化的卤代氟烷基化的第一个例子。与相关的钴催化还原偶联和 Heck 型反应不同，它通过涉及末端卤素原子转移的自由基链机制运行，从而消除了对化学计量牺牲还原剂的需求。
• Visible light photocatalytic cross-coupling and addition reactions of arylalkynes with perfluoroalkyl iodides
  作者：Yelan Xiao、Yuen-Kiu Chun、Shun-Cheung Cheng、Ruoyang Liu、Man-Kit Tse、Chi-Chiu Ko

  DOI：10.1039/d0ob01767a

  日期：——

  of arylalkynes with perfluoroalkyl iodides have been developed. Through slight modifications of the reaction conditions, reactions that are selective for the preparation of the C–C coupling product (perfluoroalkyl alkynes) and the addition products (iodo-perfluoroalkyl substituted alkenes) can be achieved. These reactions work well with different types of alkynes and perfluoroalkyl iodides. As the iodide

  已经开发了芳基炔烃与全氟烷基碘的可见光光催化交叉偶联和加成反应。通过稍微改变反应条件，可以实现对制备C-C偶联产物（全氟烷基炔）和加成产物（碘-全氟烷基取代的烯烃）有选择性的反应。这些反应适用于不同类型的炔烃和全氟烷基碘。由于由反应产生的碘化物可以用作还原剂以从其氧化形式再生光催化剂，因此不需要牺牲电子供体。