3,3'-(2,2-difluoroethenylidene)bis(fluorobenzene) | 1365658-60-1

• 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: 3,3'-(2,2-difluoroethenylidene)bis(fluorobenzene)
• 英文别名: 1-[2,2-Difluoro-1-(3-fluorophenyl)ethenyl]-3-fluorobenzene；1-[2,2-difluoro-1-(3-fluorophenyl)ethenyl]-3-fluorobenzene
• CAS: 1365658-60-1
• 化学式: C₁₄H₈F₄
• 分子量: 252.211
• InChiKey: WMQHHANHIWGNJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• 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：
  4

反应信息

• 作为反应物：
  描述：

  3,3'-(2,2-difluoroethenylidene)bis(fluorobenzene) 、 (三氟甲基)三甲基硅烷 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以74%的产率得到3,3'-(perfluoroprop-1-ene-1,1-diyl)bis(fluorobenzene)
  参考文献：
  名称：

  Mild and metal-free trifluoromethylation and pentafluoroethylation of gem-difluoroalkenes with TMSCF3 and TMSCF2CF3

  摘要：

  A direct and efficient approach for the trifluoromethylation and pentafluoroethylation of 1,1-diary1-2,2-difluoroethenes with TMSCF3 and TMSCF2CF3 in the presence of TBAF was developed. The reactions proceeded smoothly under mild reaction conditions to give the corresponding monotrifluoromethylated, bistrifluoromethylated, monopentafluoroethylated and bispentafluoroethylated products in fair to good yields, respectively, without the addition of metal catalyst. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.08.016
• 作为产物：
  描述：

  2,2-difluoro-1-iodoethenyl p-toluenesulfonate 、 3-氟苯基硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 caesium carbonate 作用下， 以 甲醇 为溶剂， 反应 22.0h， 以58%的产率得到3,3'-(2,2-difluoroethenylidene)bis(fluorobenzene)
  参考文献：
  名称：

  Consecutive cross-coupling reactions of 2,2-difluoro-1-iodoethenyl tosylate with boronic acids: efficient synthesis of 1,1-diaryl-2,2-difluoroethenes

  摘要：

  2,2-二氟-1-碘乙烯基对甲苯磺酸酯（2）与2当量硼酸在Pd(OAc)2和Na2CO3的催化下发生交叉偶联反应，高产率地生成了单偶联产物3和5。在此反应中，使用4当量硼酸在Pd(PPh3)2Cl2和Na2CO3的催化下，形成了对称双偶联产物4，产率较高。在Pd(OAc)2和Na2CO3的催化下，将3与2当量硼酸反应，高产率地得到了非对称双偶联产物4。

  DOI：

  10.3762/bjoc.9.286

文献信息

• Preparation of (2,2-difluoroethenylidene)bis(tributylstannane) and arylation reaction: efficient approach to 1,1-diaryl-2,2-difluoroethenes
  作者：Seung Yeon Han、Hyo Young Lee、Jong Hee Jeon、In Howa Jeong

  DOI：10.1016/j.tetlet.2012.01.127

  日期：2012.4

  Reaction of 2,2-difluoro-1-tributylstannylethenyl p-toluenesulfonate (1) with bis(tributyltin) in the presence of 5 mol % Pd(PPh3)4 and 30 equiv LiBr in THF at reflux temperature for 7 h afforded (2,2-difluoroethenylidene)bis(tributylstannane) (2) in a 70% yield. Coupling reaction of 2 with aryl iodides in the presence of 5 mol % Pd(PPh3)4 and 5 mol % CuI in DMF at 80 °C for 3–4 h provided the coupled

  2,2-二氟-1-三丁基苯乙烯基对甲苯磺酸酯（1）与双（三丁基锡）在5 mol％Pd（PPh 3）4和30当量LiBr的存在下于THF中在回流温度下反应7小时（2 ，（2-二氟乙烯基）双（三丁基锡烷）（2），产率为70％。偶合的反应2中5摩尔％的Pd（PPh的存在下与芳基碘化物3）4在80和5％（摩尔）的CuI在DMF℃下3-4小时提供的偶联产物3在59-85％的产率。
• Base-mediated direct fluoroalkenylation of 2-phenyl-1,3,4-oxadiazole, benzothiazole and benzoxazole with gem-difluoroalkenes
  作者：Xuxue Zhang、Yingyin Lin、Juan Zhang、Song Cao

  DOI：10.1039/c4ra13761b

  日期：——

  Direct α-fluorovinylation of 2-phenyl-1,3,4-oxadiazole, benzothiazole and benzoxazole with gem-difluoroalkenes under the assistance of KHMDS or NaH at room temperature was developed.

  2-苯基-1,3,4-噁二唑、苯并噻唑和苯并噁唑在室温下在KHMDS或NaH的辅助下与gem-二氟烯烃直接进行α-氟乙烯化反应。
• Synthesis of fluorovinyl pyrazolyl (thio)ethers by the reaction of gem -difluoroalkenes with pyrazolin-5-ones (thiones)
  作者：Tao Huang、Xianghu Zhao、Xinfei Ji、Wei Wu、Song Cao

  DOI：10.1016/j.jfluchem.2015.12.007

  日期：2016.2

  A mild and efficient method for the preparation of fluorovinyl pyrazolyl ethers and thioethers by the reaction of gem-difluoroalkenes having aryl substituents with pyrazolin-5-ones and pyrazolin-5-thiones, respectively, in the presence of t-BuOK is described.

  描述了在t- BuOK存在下通过具有芳基取代基的宝石-二氟烯烃分别与吡唑啉-5-酮和吡唑啉-5-硫酮反应来制备氟乙烯基吡唑基醚和硫醚的温和而有效的方法。
• Synthesis of fluorovinyl aryl ethers by a three-component reaction of gem-difluoroalkenes with arylboronic acids and oxygen
  作者：Mingjin Wang、Fang Liang、Yang Xiong、Song Cao

  DOI：10.1039/c4ra16468g

  日期：——

  A novel and efficient three-component reaction for the synthesis of fluorovinyl aryl ethers from gem-difluoroalkenes, arylboronic acids and oxygen under metal-free conditions is described.

  描述了在无金属条件下由宝石-二氟烯烃，芳基硼酸和氧合成氟乙烯基芳基醚的新颖且有效的三组分反应。
• Consecutive cross-coupling reactions of 2,2-difluoro-1-iodoethenyl tosylate with boronic acids: efficient synthesis of 1,1-diaryl-2,2-difluoroethenes
  作者：Ju Hee Kim、Su Jeong Choi、In Howa Jeong

  DOI：10.3762/bjoc.9.286

  日期：——

  The cross-coupling reactions of 2,2-difluoro-1-iodoethenyl tosylate (2) with 2 equiv of boronic acids in the presence of catalytic amounts of Pd(OAc)₂ and Na₂CO₃ afforded the mono-coupled products 3 and 5 in high yields. The use of 4 equiv of boronic acids in the presence of catalytic amount of Pd(PPh₃)₂Cl₂ and Na₂CO₃ in this reaction resulted in the formation of symmetrical di-coupled products 4 in high yields. Unsymmetrical di-coupled products 4 were obtained in high yields from the reactions of 3 with 2 equiv of boronic acids in the presence of catalytic amounts of Pd(OAc)₂ and Na₂CO_3.

  2,2-二氟-1-碘乙烯基对甲苯磺酸酯（2）与2当量硼酸在Pd(OAc)2和Na2CO3的催化下发生交叉偶联反应，高产率地生成了单偶联产物3和5。在此反应中，使用4当量硼酸在Pd(PPh3)2Cl2和Na2CO3的催化下，形成了对称双偶联产物4，产率较高。在Pd(OAc)2和Na2CO3的催化下，将3与2当量硼酸反应，高产率地得到了非对称双偶联产物4。