(1-(4-(trifluoromethyl)phenyl)ethene-1,2-diyl)dibenzene | 6565-03-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1-(4-(trifluoromethyl)phenyl)ethene-1,2-diyl)dibenzene
• 英文别名: 1,1'-{1-[4-(Trifluoromethyl)phenyl]ethene-1,2-diyl}dibenzene；1-(1,2-diphenylethenyl)-4-(trifluoromethyl)benzene
• CAS: 6565-03-3
• 化学式: C₂₁H₁₅F₃
• 分子量: 324.345
• InChiKey: HETARWWQBZOSDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1-(4-(trifluoromethyl)phenyl)ethene-1,2-diyl)dibenzene 在 溴 作用下， 以 溶剂黄146 为溶剂， 生成 2-Brom-1,2-diphenyl-1-<4-trifluormethyl-phenyl>-aethylen
  参考文献：
  名称：

  Buu-Hoi,N.P. et al., Recueil des Travaux Chimiques des Pays-Bas, 1966, vol. 85, p. 367 - 372

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲醇 在 4-二甲氨基吡啶 、 双(乙腈)氯化钯(II) 、 1,3-双(二苯基膦)丙烷 、 三乙胺 、 lithium tert-butoxide 作用下， 以 四氢呋喃 为溶剂， 反应 19.5h， 生成 (1-(4-(trifluoromethyl)phenyl)ethene-1,2-diyl)dibenzene
  参考文献：
  名称：

  N-甲苯磺酰腙与磷酸苄酯的 Pd 催化偶联：迈向二或三取代烯烃的合成

  摘要：

  该研究表明，通过将N-甲苯磺酰腙 (NTH) 与磷酸苄基作为亲电伙伴偶联，可以以良好至高产率获得各种具有高化学选择性的二取代和三取代烯烃。得到的新型催化体系由PdCl 2 (CH 3 CN) 2 /dppp、LiO t Bu为碱、环戊基甲基醚为绿色溶剂组成。此外，我们使用 NTH 衍生物和具有 C sp 2 -Cl 键的苄基磷酸酯进行了克级转化。后者被用作关键中间体进一步后功能化的起点。

  DOI：

  10.1021/acs.joc.1c02580

文献信息

• Rhodium catalyzed reaction of internal alkynes with organoborons under CO atmosphere: a product tunable reaction
  作者：Levent Artok、Melih Kuş、Özge Aksın-Artok、Fatma Nurcan Dege、Fatma Yelda Özkılınç

  DOI：10.1016/j.tet.2009.09.044

  日期：2009.11

  Alkynes react with organoborons under a CO atmosphere in the presence of a rhodium(I) catalyst to afford mainly 5-aryl-2(5H)-furanones, α,β-unsaturated ketones, and indanones. The product selectivity can be tuned by modifying the reaction conditions.

  炔烃在铑（I）催化剂存在下，在CO气氛下与有机硼反应，主要生成5-芳基-2（5 H）-呋喃酮，α，β-不饱和酮和茚满酮。产物的选择性可以通过改变反应条件来调节。
• Cross-coupling reaction of thermally stable titanium(ii)-alkyne complexes with aryl halides catalysed by a nickel complex
  作者：Yasushi Obora、Hiroyuki Moriya、Makoto Tokunaga、Yasushi Tsuji

  DOI：10.1039/b310565b

  日期：——

  The first cross-coupling reaction of thermally stable titanium(II)–alkyne complexes with aryl iodides in the presence of a catalytic amount of Ni(cod)2 is presented.

  首次报道了热稳定的钛(II)–炔烃络合物与芳基碘化物在催化量的Ni(cod)2存在下的交叉耦合反应。
• Nickel-Catalyzed Hydroarylation of Alkynes under Reductive Conditions with Aryl Bromides and Water
  作者：E. Ryan Barber、Hannah M. Hynds、Claudia P. Stephens、Holli E. Lemons、Emily T. Fredrickson、Dale J. Wilger

  DOI：10.1021/acs.joc.9b01556

  日期：2019.9.20

  coupling reaction utilizes commercially available alkynes and aryl bromides, along with water and Zn. An air-stable and easily synthesized Ni(II) precatalyst is the only entity used in the reaction that is not commercially available. This reductive cross-coupling reaction displays a fairly unusual anti selectivity when aryl bromides with ortho substituents are used. In addition to optimization data

  描述了用于炔烃的操作简单的镍催化的氢芳基化反应。这种三组分偶联反应利用市售的炔烃和溴化芳基，以及水和锌。空气稳定且易于合成的Ni（II）预催化剂是该反应中使用的唯一实体，该实体不可商购。当使用具有邻位取代基的芳基溴化物时，该还原性交叉偶联反应显示出相当不寻常的抗选择性。除了优化数据和初步的底物范围外，还使用包括氘标记研究在内的补充实验来提供初步的催化机理。我们认为该报告应能激发并告知其他Ni催化的碳官能化反应。
• Pd-catalyzed Heck reactions of aryl bromides with 1,2-diarylethenes
  作者：Jones Limberger、Silvia Poersch、Adriano L Monteiro

  DOI：10.1590/s0103-50532011000700026

  日期：——

  A catalytic system composed of Pd(OAc)(2) and P(o-tol)(3) was found to be effective for the Heck reaction of aryl bromides with diarylethylenes. Using K(2)CO(3) as a base and DMF as a solvent, trisubstituted olefins were obtained in good to excellent yields. Aryl bromides containing an electron-withdrawing group in para position were less reactive for the Heck coupling reaction and gave substantial amount of homocoupling by-product suggesting that oxidative addition is not the rate-determining step. Electron withdrawing group substituent in the para position of stilbene affects the regioselectivity of the reaction. In this case, the phenyl group from the Ph-Pd complex migrates preferentially to the same carbon of the double bond to which the phenyl is bonded. Finally, a one pot sequential double Heck arylation of styrene was performed, giving trisubstituted olefin with an overall yield of 73%.
• Pd-Catalyzed Coupling of <i>N</i>-Tosylhydrazones with Benzylic Phosphates: Toward the Synthesis of Di- or Tri-Substituted Alkenes
  作者：Kena Zhang、Olivier Provot、Mouad Alami、Christine Tran、Abdallah Hamze

  DOI：10.1021/acs.joc.1c02580

  日期：2022.1.21

  in good to high yields by coupling N-tosylhydrazones (NTHs) with benzylic phosphates as electrophilic partners. The obtained new catalytic system consisted of PdCl2(CH3CN)2/dppp, LiOtBu as a base, and cyclopentyl methyl ether as a green solvent. In addition, we performed a gram-scale transformation using NTH derivatives and benzylic phosphates having a C sp2–Cl bond. The latter was used as a starting

  该研究表明，通过将N-甲苯磺酰腙 (NTH) 与磷酸苄基作为亲电伙伴偶联，可以以良好至高产率获得各种具有高化学选择性的二取代和三取代烯烃。得到的新型催化体系由PdCl 2 (CH 3 CN) 2 /dppp、LiO t Bu为碱、环戊基甲基醚为绿色溶剂组成。此外，我们使用 NTH 衍生物和具有 C sp 2 -Cl 键的苄基磷酸酯进行了克级转化。后者被用作关键中间体进一步后功能化的起点。