(E)-1-氟-1-苯基-2-碘乙烯 | 61378-39-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (E)-1-氟-1-苯基-2-碘乙烯
• 英文名称: (Z)-1-fluoro-2-iodo-1-phenylethylene
• 英文别名: (Z)-2-fluoro-1-iodo-2-phenylethene；(Z)-2-fluoro-1-iodo-3-phenylethene；(Z)-1-Fluor-2-jod-1-phenylethylen；[(Z)-1-fluoro-2-iodoethenyl]benzene
• CAS: 61378-39-0
• 化学式: C₈H₆FI
• 分子量: 248.039
• InChiKey: CTPMQUDSAMZGHN-VURMDHGXSA-N

物化性质

• 沸点：
  217.7±33.0 °C(Predicted)
• 密度：
  1.752±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1-氟-1-苯基-2-碘乙烯 、 苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 作用下， 以 苯 为溶剂， 反应 1.5h， 以85%的产率得到(Z)-(1-fluoro-2-phenylethenyl)benzene
  参考文献：
  名称：

  Stereoselective synthesis of fluoroalkenes via (Z)-2-fluoroalkenyliodonium salts

  摘要：

  Stereoselective synthesis of fluoroalkenes is described. (Z)-2-Fluoro-1-alkenyl(phenyl)iodonium tetrafluoroborates (1) were synthesized stereoselectively in good yields by Michael-type addition of HF to 1-alkynyl(phenyl)iodonium tetrafluoroborates (2) with a commercially available HF reagent, hydrofluoric acid or Et3N-3HF. Pd-catalyzed cross-coupling reactions using 1 gave (Z)-2-fluoro-l-alkene derivatives in moderate yields. The treatment of 1 with KI in the presence of a catalytic amount of CuI gave (Z)-2-fluoro-1-iodo-1-alkenes (3). Pd-catalyzed cross-coupling reactions of 3 gave better results than that of 1, and a variety of (Z)-2-fluoro-l-alkene derivatives were synthesized in good yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.085
• 作为产物：
  描述：

  (碘乙炔基)苯 在 ammonium tetrafluoroborate 、 [Au(N,N’-bis-[2,6-(di-iso-propyl)phenyl]imidazolidin-2-ylidene)(NEt₃)][HF₂] 、 triethylamine tris(hydrogen fluoride) 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以88%的产率得到(E)-1-氟-1-苯基-2-碘乙烯
  参考文献：
  名称：

  金（I）和钯（II）N-杂环碳烯配合物催化的炔烃和烯烃的顺序官能化

  摘要：

  据报道，在Au I- NHC（NHC = N-杂环卡宾）催化剂存在下，使用N-碘代琥珀酰亚胺用于合成1-碘代炔烃的末端炔烃加碘。在温和的反应条件下，一系列芳烃成功地以良好的产率转化为相应的1-碘炔烃。通过选择性的Au I催化的氢氟化反应生成（Z）-2-氟-1-碘代烯烃，进一步证明了这些化合物作为有机结构单元的进一步使用以及金属-NHC络合物作为炔烃功能化催化剂的有利选择。由Suzuki–Miyaura与Pd II催化的芳基硼酸交叉偶联‐NHC络合物，可访问三取代（Z）–氟代烯烃。所有方法均可在优化的单个反应条件中仅进行很小的变化即可依次执行，从而在所有情况下均保持高效和高选择性，因此可从市售的末端炔烃中直接获得有价值的氟化烯烃。

  DOI：

  10.1002/cctc.201600868

文献信息

• Selective Mono- and Dialkynylation of 1-Fluoro-2,2-diiodovinylarenes Using Pd-Catalyzed Decarboxylative Coupling Reactions
  作者：Aravindan Jayaraman、Sunwoo Lee

  DOI：10.1021/acs.orglett.9b02907

  日期：2019.10.4

  Palladium-catalyzed decarboxylative coupling reactions using alkynoic acids and 1-fluoro-2,2-diiodovinylarenes provide mono- and dialkynylfluoroalkenes with high selectivity. When the reaction was conducted using DBU/DMSO, the hydrodeiodinated monoalkynylfluoroalkene product was formed, whereas performing the reaction using Et3N/THF gave the dialkynylfluoroalkene product. Both reaction conditions gave high yields of

  使用炔酸和1-氟-2,2-二碘乙烯基芳烃的钯催化的脱羧偶联反应可提供高选择性的单-和二-炔基氟烯烃。当使用DBU / DMSO进行反应时，形成了加氢碘化的单炔基氟代烯烃产物，而使用Et 3 N / THF进行反应则得到了二炔基氟代烯烃产物。两种反应条件均产生了高产率的带有氟原子的所需烯炔和乙炔产物。
• Polymers as Reagents and Catalysts. XI. Stereospecific Iodofluorination of Alkenes in the Presence of Polymer Supported Hydrogen Fluoride
  作者：Ana Gregorcic、Marko Zupan

  DOI：10.1246/bcsj.60.3083

  日期：1987.8

  N-Iodosuccinimide reacted with phenyl substituted alkenes in the presence of insoluble polymer supported hydrogen fluoride, which was prepared by reaction of hydrogen fluoride with crosslinked poly(styrene-co-4-vinylpyridine) containing 40–45 mol% of 4-vinylpyridine, thus forming vicinal iodofluorides in high yields. Reactions proceeded with Markovnikov type regioselectivity, and in the case of (Z)-

  N-碘代琥珀酰亚胺与苯基取代的烯烃在不溶性聚合物负载的氟化氢存在下反应，氟化氢与含有40-45 mol% 4-乙烯基吡啶的交联聚（苯乙烯-co-4-乙烯基吡啶）反应制备，因此以高产率形成邻位碘氟化物。反应以马尔科夫尼科夫型区域选择性进行，在 (Z)- 和 (E)-芪的情况下，还观察到 (Z)- 和 (E)-1- 苯基丙烯和茚反立体定向性。苯基取代的乙炔的碘氟化发生区域和立体特异性，形成 (Z)-1-氟-2-碘-1-苯基烯烃，其产率低于在烯烃情况下观察到的产率。
• Iodofluorination of 1-Phenyl-1-alkynes with Methyliodine(III) Difluoride
  作者：Marko ZUPAN

  DOI：10.1055/s-1976-24090

  日期：——
• GREGORIC, ANA;ZUPAN, MARKO, BULL. CHEM. SOC. JAP., 60,(1987) N 8, 3083-3085
  作者：GREGORIC, ANA、ZUPAN, MARKO

  DOI：——

  日期：——
• Stereoselective synthesis of fluoroalkenes via (Z)-2-fluoroalkenyliodonium salts
  作者：Masanori Yoshida、Ayumu Komata、Shoji Hara

  DOI：10.1016/j.tet.2006.05.085

  日期：2006.9

  Stereoselective synthesis of fluoroalkenes is described. (Z)-2-Fluoro-1-alkenyl(phenyl)iodonium tetrafluoroborates (1) were synthesized stereoselectively in good yields by Michael-type addition of HF to 1-alkynyl(phenyl)iodonium tetrafluoroborates (2) with a commercially available HF reagent, hydrofluoric acid or Et3N-3HF. Pd-catalyzed cross-coupling reactions using 1 gave (Z)-2-fluoro-l-alkene derivatives in moderate yields. The treatment of 1 with KI in the presence of a catalytic amount of CuI gave (Z)-2-fluoro-1-iodo-1-alkenes (3). Pd-catalyzed cross-coupling reactions of 3 gave better results than that of 1, and a variety of (Z)-2-fluoro-l-alkene derivatives were synthesized in good yields. (c) 2006 Elsevier Ltd. All rights reserved.