1-iodo-1-perfluorooctyne | 58292-95-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代乙炔及其衍生物
• 英文名称: 1-iodo-1-perfluorooctyne
• 英文别名: 3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluoro-1-iodooct-1-yne
• CAS: 58292-95-8
• 化学式: C₈F₁₃I
• 分子量: 469.972
• InChiKey: JWOJAGFUNODSPU-UHFFFAOYSA-N

物化性质

• 沸点：
  164.1±40.0 °C(Predicted)
• 密度：
  2.009±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  1-iodo-1-perfluorooctyne 在 copper(l) iodide 、 三乙胺 、 二异丙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 1H,1H,2H,2H-perfluoro-3,5-dodecadiynyl acrylate
  参考文献：
  名称：

  Synthesis of two new families of fluorinated compounds: 1H,1H,2H,2H-perfluoro-3,5-alkyldiynols and 1H,1H-perfluoro-2,4-alkyldiynols and their acrylates and methacrylates

  摘要：

  The synthesis of two new families of compounds, 1H,1H,2H,2H-perfluoro-3,5-alkyldiynols and 1H,1H-perfluoro-2,4-alkyldiynols, and their acrylates and methacrylates, precursors of polymeric systems with important physical properties, is described. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.03.053
• 作为产物：
  描述：

  perfluoro-1-octynylmagnesium bromide 在 碘 作用下， 生成 1-iodo-1-perfluorooctyne
  参考文献：
  名称：

  全氟炔基卤化镁的一些意外反应

  摘要：

  ř ˚F用AcCCMgX发生反应2 O操作得到不仅的MeC（O）CCR ˚F而且（O）CXC（R的MeC ˚F）C（O）Me和与CF 3 COOPr它给CF 3 C（O）CHC（OPR）R ˚F不CF 3 C（O）CCR ˚F ; ř ˚F CCMgBr有Cl反应2生成R ˚F CCBr而非ř ˚F CCCl，同时用溴2 - [R ˚F CCMgI同样给出ř ˚F CCI而非ř ˚F CCBr。

  DOI：

  10.1016/s0022-328x(00)95207-0

文献信息

• Reaction of (perfluoroalkyl)alkynes with iodine and some of its derivatives
  作者：Patrice Moreau、Auguste Commeyras

  DOI：10.1039/c39850000817

  日期：——

  Iodine and some of is derivatives, such as ICI, ICN, and IF, react, under relatively mild conditions, with (perfluoroalkyl)alkynes RF–CC–H to afford regiospecifically the corresponding 1-iodo perfluorinated alkenes.

  碘和某些衍生物（例如ICI，ICN和IF）在相对温和的条件下与（全氟烷基）炔烃R F – C C–H反应，以区域特异性地提供相应的1-碘全氟烯烃。
• Preparation of first examples of RFCCIF4 molecules. A study of the fluorination of selected 1-iodoalk-1-ynes with xenon difluoride/boron trifluoride
  作者：Vadim V. Bardin、Hermann-Josef Frohn

  DOI：10.1016/j.jfluchem.2013.01.006

  日期：2013.2

  First examples of alk-1-yn-1-yliodine(V) molecules, CF3CCIF4 and C6F13CCIF4, were prepared by fluorination of the corresponding 1-iodoperfluoroalk-1-ynes with XeF2 in 1,1,1,3,3-pentafluorobutane (PFB) in the presence of BF3. The reaction of 1-iodo-2-(4-heptafluorotolyl)ethyne, 4-CF3C6F4CCI, with XeF2 (1.5 equiv) and BF3 resulted in a mixture of 4-CF3C6F4CCIF2 (main product), 4-CF3C6F4CCIF4, and tr

  烷-1-炔-1- yliodine的第一实施例（V）的分子，CF 3 Ç CIF 4和C 6 ˚F 13 Ç CIF 4中，通过相应的1- iodoperfluoroalk -1-炔的氟化制备的氟化氙2在1 ，在BF的存在1,1,3,3-五氟丁烷（PFB）3。1-碘-2-（4- heptafluorotolyl）乙炔的反应中，4-CF 3 C ^ 6 ˚F 4 Ç CI，具有的XeF 2（1.5当量）和BF 3导致的4-CF混合物3 Ç 6 ˚F 4 ç CIF 2（主产物），4-CF 3 C ^ 6 ˚F 4 Ç CIF 4，和反式- （4- CF 3 Ç 6 ˚F 4）CF CFI，而3当量的XeF的作用下2 / BF 3的复合混合物polyfluoroorganics和IF 5结果。非氟代的4 ħ 9 Ç CI与氟化氙反应2 / BF 3优先下跨过三键氟加成并给主要是C 4 ħ 9 CF
• The preparation of HCF2CdX and HCF2ZnX via direct insertion into the carbon halogen bond of CF2HY (Y=Br, I)
  作者：Donald J. Burton、Greg A. Hartgraves

  DOI：10.1016/j.jfluchem.2007.05.015

  日期：2007.10

  The difluoromethylcadmium and zinc reagents have been prepared in DMF via direct insertion of Cd-0 into the carbon halogen bond of CF2HY (Y = Br, I). These reagents are stable at 65-75 degrees C and exhibit prolonged stability and activity at room temperature. Metathesis of the difluoromethylcadmium reagents with Cu(I)X (X = Br, Cl) at -55 degrees C rapidly produces difluoromethylcopper. The copper reagent is significantly less stable than the cadmium or zinc reagent and rapidly decomposes at room temperature. The difluoromethylcadmium and copper reagents exhibit good reactivity with allylic halides, propargylic derivatives and 1-iodoalkynes to provide good yields of the corresponding difluoromethylalkenes, difluoromethylallenes and difluoromethyl-2-alkynes. Alkylation is successful only with reactive alkyl halides. Generally, the difluoromethylcopper reagent is more reactive than the difluoromethylcadmium reagent and generally exhibits higher regioselectivity in reactions that can occur by either alpha- or -gamma-attack. (C) 2007 Elsevier B.V. All rights reserved.
• Stereoselective Synthesis of (<i>Z</i>)-Perfluoroalkyl-1-iodo-1-triisopropyl Silylalkenes: A Convenient Route to Perfluoroalkyl-Substituted Unsaturated Synthons
  作者：Juan Francisco Chesa、Dolores Velasco、Francisco López-Calahorra

  DOI：10.1080/00397910903161843

  日期：2010.5.19

  The quantitative and fully stereoselective synthesis of (Z)-perfluoroalkyl-1-iodo-1-triisopropylsilylalkenes and their easy, high-yielding transformation into the corresponding 1-iodo-2-perfluoroacetylenes and (Z)-2-perfluoroalkyl-1-iodo-1-alkenes, compounds of interest as synthons for classical organometallic chemistry or for metal-catalyzed coupling reactions, are discussed.
• Some unexpected reactions of perfluoroalkynylmagnesium halides
  作者：G. Santini、M. Le Blanc、J.G. Riess

  DOI：10.1016/s0022-328x(00)95207-0

  日期：1975.12

  RFCCMgX reacts with Ac2O to give not only MeC(O)CCRF but also MeC(O)CXC(RF)C(O)Me, and with CF3COOPr it gives CF3C(O)CHC(OPr)RF not CF3C(O)CCRF; RFCCMgBr reacts with Cl2 to give RFCCBr rather than RFCCCl, while with Br2 RFCCMgI similarly gives RFCCI rather than RFCCBr.

  ř ˚F用AcCCMgX发生反应2 O操作得到不仅的MeC（O）CCR ˚F而且（O）CXC（R的MeC ˚F）C（O）Me和与CF 3 COOPr它给CF 3 C（O）CHC（OPR）R ˚F不CF 3 C（O）CCR ˚F ; ř ˚F CCMgBr有Cl反应2生成R ˚F CCBr而非ř ˚F CCCl，同时用溴2 - [R ˚F CCMgI同样给出ř ˚F CCI而非ř ˚F CCBr。