(Z)-2,3,3,3-tetrafluoro-1-iodoprop-1-ene | 672339-38-7

• 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: (Z)-2,3,3,3-tetrafluoro-1-iodoprop-1-ene
• 英文别名: 1-Propene,2,3,3,3-tetrafluoro-1-iodo-, (1Z)-
• CAS: 672339-38-7
• 化学式: C₃HF₄I
• 分子量: 239.939
• InChiKey: UNHLMLCCHROJMY-UPHRSURJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-碘-3-硝基苯 、 (Z)-2,3,3,3-tetrafluoro-1-iodoprop-1-ene 在 正丁基锂 、 dichloro(N,N,N’,N‘-tetramethylethylenediamine)zinc 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 12.0h， 以76%的产率得到1-硝基-3-(3,3,3-三氟丙-1-炔基)苯
  参考文献：
  名称：

  Facile syntheses of various per- or polyfluoroalkylated internal acetylene derivatives

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(03)01199-2
• 作为产物：
  描述：

  1,1,1,2,2-五氟-3-碘丙烷 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 生成 (Z)-2,3,3,3-tetrafluoro-1-iodoprop-1-ene
  参考文献：
  名称：

  Highly stereoselective approach to 3-fluoroalkylated (E)-hex-3-ene-1,5-diyne derivatives via an addition–elimination reaction

  摘要：

  Palladium(0)-catalyzed Sonogashira cross-coupling reaction of 2-fluoroalkylated (Z)-2-fluoro-1-iodoethene, which is easily prepared from commercially available polyfluorinated alcohols in facile three steps, with terminal alkynes in DMF at room temperature for 24 h took place stereospeciflcally to give the corresponding 1-fluoroalkylated (Z)-1-fluorobut-1-en-3-yne derivatives in good to excellent yield. Thus obtained fluoroalkylated 1-fluoroenynes were effectively subjected to addition elimination reaction with various alkynyllithiums at room temperature, leading to 3-fluoroalkylated hex-3-ene-1,5-diyne derivatives in good to high yields with an excellent E selectivity. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2013.09.010

文献信息

• Stereoselective synthesis of CF3-substituted trans- and cis-enediynes via carbocupration or hydrostannation reactions of CF3-containing diyne
  作者：Tsutomu Konno、Misato Kishi、Takashi Ishihara、Shigeyuki Yamada

  DOI：10.1016/j.tet.2014.02.015

  日期：2014.4

  smoothly subjected to carbocupration reaction with various organocuprates, followed by treatment of the resultant carbocupration adducts with iodine, the corresponding vinyl iodides being formed in good yields in a cis-addition manner. Thus obtained iodide could be successfully converted into CF3-substituted trans-enediynes in high yields. Also, hydrostannation reaction of the diyne proceeded well in a

  由（Z）-2,3,3,3-四氟-1-碘代丙-1-烯容易地分两步制备的含CF 3的二炔，与各种有机铜化合物进行碳cup合反应，然后对其进行处理与碘的碳cup合加合物，相应的乙烯基碘化物以顺式加成的方式高收率地形成。如此获得的碘可以高收率成功地转化为CF 3取代的反式二烯炔。此外，二炔的反应hydrostannation在进展顺利反-addition方式，得到高产率的相应的乙烯基锡烷。还发现乙烯基锡烷可有效转化为CF 3-高取代度的顺式-二烯二炔。
• Highly stereoselective approach to 3-fluoroalkylated (E)-hex-3-ene-1,5-diyne derivatives via an addition–elimination reaction
  作者：Tsutomu Konno、Misato Kishi、Takashi Ishihara、Shigeyuki Yamada

  DOI：10.1016/j.jfluchem.2013.09.010

  日期：2013.12

  Palladium(0)-catalyzed Sonogashira cross-coupling reaction of 2-fluoroalkylated (Z)-2-fluoro-1-iodoethene, which is easily prepared from commercially available polyfluorinated alcohols in facile three steps, with terminal alkynes in DMF at room temperature for 24 h took place stereospeciflcally to give the corresponding 1-fluoroalkylated (Z)-1-fluorobut-1-en-3-yne derivatives in good to excellent yield. Thus obtained fluoroalkylated 1-fluoroenynes were effectively subjected to addition elimination reaction with various alkynyllithiums at room temperature, leading to 3-fluoroalkylated hex-3-ene-1,5-diyne derivatives in good to high yields with an excellent E selectivity. (C) 2013 Elsevier B.V. All rights reserved.
• 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.