(E)-1,1,1,2,2,3,3,4,4-nonafluoro-6-iodo-5-dodecene | 109574-88-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (E)-1,1,1,2,2,3,3,4,4-nonafluoro-6-iodo-5-dodecene
• 英文别名: (E)-1-Perfluorobutyl-2-iodo-octene；(E)-1,1,1,2,2,3,3,4,4-nonafluoro-6-iodododec-5-ene；1,1,1,2,2,3,3,4,4-nonafluoro-6-iodododec-5-ene；(5E)-1,1,1,2,2,3,3,4,4-Nonafluoro-6-iodododec-5-ene
• CAS: 109574-88-1
• 化学式: C₁₂H₁₄F₉I
• 分子量: 456.133
• InChiKey: HLLNKYADPLDRRE-BQYQJAHWSA-N

物化性质

• 沸点：
  272.1±40.0 °C(Predicted)
• 密度：
  1.583±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (E)-1,1,1,2,2,3,3,4,4-nonafluoro-6-iodo-5-dodecene 在 甲醇 、 正丁基锂 作用下， 生成 (E)-1-Perfluorobutyl-octene
  参考文献：
  名称：

  将全氟丁基碘加到碳-碳多键上并制备全氟丁基烯烃

  摘要：

  在超声辐射或相转移条件下，连二亚硫酸钠可有效地将全氟丁基碘加到CC多个键上。全氟丁基取代的烯烃可以通过碱催化的消除反应从β-碘-全氟烷烃和烯烃中获得。还原性裂解。

  DOI：

  10.1016/s0040-4039(00)97911-5
• 作为产物：
  描述：

  1-辛炔 、 全氟碘代丁烷 在 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 以87%的产率得到(E)-1,1,1,2,2,3,3,4,4-nonafluoro-6-iodo-5-dodecene
  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

• Radical Addition of Perfluoroalkyl Iodides to Alkenes and Alkynes Initiated by Sodium Dithionite in an Aqueous Solution in the Presence of a Novel Fluorosurfactant
  作者：Zhiwei Xiao、Huawei Hu、Jiaoli Ma、Qingyun Chen、Yong Guo

  DOI：10.1002/cjoc.201300433

  日期：2013.7

  fluoroalkylation to occur in the water without adding organic solvent. The addition of perfluoroalkyl iodides with olefins and alkynes under the initiation of Na2S2O4 in water in the presence of the fluorosurfactant gave the corresponding adducts in good to excellent yields. The fluorosurfactant was suitable for a radical addition process.

  制备并表征了一种新型的氟化阴离子表面活性剂Cl（CF 2）6 O（CF 2）2 SO 3 N（C 2 H 5）4。含氟表面活性剂的应用使氟烷基化在水中发生而无需添加有机溶剂。在含氟表面活性剂的存在下，在水中在Na 2 S 2 O 4的引发下，将全氟烷基碘化物与烯烃和炔烃加成，得到相应的加合物，收率良好或优异。含氟表面活性剂适用于自由基加成过程。
• Metal-Free Iodoperfluoroalkylation: Photocatalysis versus Frustrated Lewis Pair Catalysis
  作者：Constantin Czekelius、Lucas Helmecke、Michael Spittler、Bernd M. Schmidt

  DOI：10.1055/s-0040-1707232

  日期：2021.1

  Professor Rolf Huisgen Abstract A comparison of two catalytic, metal-free iodoperfluoro­alkylation protocols is presented. Frustrated Lewis pairs [ t Bu3P/B(C6F5)3] or phosphines/phosphites under visible light irradiation efficiently mediate the functionalization of non-activated alkenes and alkynes. A comprehensive account of the corresponding substrate scopes as well as insights into the mechanistic details

  纪念Rolf Huisgen教授 抽象 比较了两种催化的，无金属的碘代氟烷基化方案。沮丧的路易斯对[ t Bu 3 P / B（C 6 F 5）3 ]或膦/亚磷酸盐在可见光辐射下有效地介导了未活化的烯烃和炔烃的官能化。提供了对相应底物范围的全面介绍，以及对两种反应途径的机理细节的见解。
• Simple Synthesis of Fluorinated Ene-Ynes via In Situ Generation of Allenes
  作者：Ellen M. Sletten、Joseph A. Jaye

  DOI：10.1055/s-0037-1610774

  日期：2021.11

  Fluorination of small molecules is a key route toward modulating reactivity and bioactivity. The 1,3 ene-yne functionality is an important synthon towards complex products, as well as a common functionality in biologically active molecules. Here, we present a new synthetic route towards fluorinated ene-ynes from simple starting materials. We employ gas chromatography-mass spectrometry analysis to probe

  小分子的氟化是调节反应性和生物活性的关键途径。1,3 烯-炔官能团是合成复杂产物的重要合成子，也是生物活性分子中的常见官能团。在这里，我们提出了一种从简单起始材料合成氟化烯炔的新途径。我们采用气相色谱-质谱分析来探测这种转化所需的连续消除，并观察丙二烯中间体。烯-炔产物的含氟量足以通过含氟萃取进行纯化。这种方法将允许轻松访问功能性氟烯炔。
• Facile syntheses of various per- or polyfluoroalkylated internal acetylene derivatives
  作者：Tsutomu Konno、Jungha Chae、Masashi Kanda、Go Nagai、Kazushige Tamura、Takashi Ishihara、Hiroki Yamanaka

  DOI：10.1016/s0040-4020(03)01199-2

  日期：2003.9

  Treatment of per- or polyfluoroalkylated vinyl iodides 5 with 2 equiv. of n-BuLi in THF produced the corresponding lithium acetylides in situ, which were transformed into zinc acetylides by the addition of ZnCl2.TMEDA complex into the reaction mixture. The in situ generated zinc acetylides were exposed to the cross-coupling conditions such as ArI/cat. Pd(PPh3)(4), reflux, 6-12 h, giving rise to the desired per- or polyfluoroalkylated acetylenes in high yields. In the case of trifluoromethylated acetylene, commercially available 2-bromo-3,3,3-trifluoropropene 6 could also be used instead of 5 as the starting material. In the acetylenes having a fluoroalkyl group and an aliphatic side chain, vinyl iodides 7, prepared by radical addition of perfluoroalkyl iodide to terminal acetylenes, were treated with t-BuOK at room temperature or at the reflux temperature of benzene, affording the desired compounds in good yields. (C) 2003 Elsevier Ltd. All rights reserved.
• Iron-Catalyzed 1,2-Addition of Perfluoroalkyl Iodides to Alkynes and Alkenes
  作者：Tao Xu、Chi Wai Cheung、Xile Hu

  DOI：10.1002/anie.201402511

  日期：2014.5.5

  Iron catalysis has been developed for the intermolecular 1,2‐addition of perfluoroalkyl iodides to alkynes and alkenes. The catalysis has a wide substrate scope and high functional‐group tolerance. A variety of perfluoroalkyl iodides including CF3I can be employed. The resulting perfluoroalkylated alkyl and alkenyl iodides can be further functionalized by cross‐coupling reactions. This methodology

  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。