4,4,4-trifluoro-2-(4-fluorophenyl)butanenitrile

• 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: 4,4,4-trifluoro-2-(4-fluorophenyl)butanenitrile
• 英文别名: 4,4,4-Trifluoro-2-(4-fluorophenyl)butanenitrile
• 化学式: C₁₀H₇F₄N
• 分子量: 217.166
• InChiKey: RHIGYMGNHLFVNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(三氟甲基)-1,2-苯碘酰-3(1H)-酮 、 4-氟苯乙烯 、 氰化亚铜 在 三环己基膦 作用下， 以 氘代氯仿 为溶剂， 反应 18.0h， 以73%的产率得到4,4,4-trifluoro-2-(4-fluorophenyl)butanenitrile
  参考文献：
  名称：

  Copper-Mediated Cyanotrifluoromethylation of Styrenes Using the Togni Reagent

  摘要：

  Styrenes with an electron-deficient double bond undergo cyanotrifluoromethylation with a trifluoromethylated hypervalent iodine reagent in the presence of CuCN. The reaction proceeds under mild conditions in the presence of bulky phosphines or B(2)pin(2) additives. The process is highly regioselective and involves the consecutive formation of two C-C bonds in a single addition reaction. In the presence of a p-methoxy substituent in the styrene, oxytrifluoromethylation occurs instead of the cyanotrifluoromethylation.

  DOI：

  10.1021/jo401831t

文献信息

• Highly shape- and regio-selective peroxy–trifluoromethylation of styrene by metal–organic framework Cu₃(<b>BTC</b>)₂
  作者：Bo Qi、Tiexin Zhang、Mochen Li、Cheng He、Chunying Duan

  DOI：10.1039/c7cy01892d

  日期：——

  The peroxy and trifluoromethyl groups play important roles in pharmacy, but it is challenging to introduce both of them selectively into the target molecules in a homogeneous catalytic system.

  过氧基和三氟甲基基团在药学中起着重要作用，但在均相催化体系中有挑战性地将它们两者有选择地引入目标分子中。
• A Readily Available Trifluoromethylation Reagent and Its Difunctionalization of Alkenes
  作者：Min Zhang、Jin-Hong Lin、Ji-Chang Xiao

  DOI：10.1021/acs.orglett.1c02146

  日期：2021.8.6

  Trifluoromethyl substitution is notably popular in pharmaceuticals and agrochemicals; however, trifluoromethylated compounds normally rely on the use of cost-prohibitive or gaseous trifluoromethylating reagents, which diminishes the general applicability of these methods. Herein an efficient trifluoromethylation reagent trifluoromethylsulfonyl–pyridinium salt (TFSP) was reported, which can be readily

  三氟甲基取代在药物和农用化学品中特别受欢迎；然而，三氟甲基化化合物通常依赖于成本过高或气态三氟甲基化试剂的使用，这降低了这些方法的普遍适用性。本文报道了一种有效的三氟甲基化试剂三氟甲基磺酰基-吡啶鎓盐（TFSP），它可以很容易地从廉价且容易获得的大宗工业原料中制备。TFSP可以在光催化下产生三氟甲基自由基，实现烯烃有效的叠氮或氰基三氟甲基化反应。
• Copper-Catalyzed Intermolecular Cyanotrifluoromethylation of Alkenes
  作者：Yu-Tao He、Lian-Hua Li、Yan-Fang Yang、Zhao-Zhao Zhou、Hui-Liang Hua、Xue-Yuan Liu、Yong-Min Liang

  DOI：10.1021/ol403263c

  日期：2014.1.3

  A novel and highly practical reaction for the copper-catalyzed intermolecular cyanotrifluoromethylation of alkenes is presented here. This methodology provides a general and straightforward way to synthesize a variety of useful CF3-containing nitriles, which can be used for further preparation of pharmaceutically and agrochemically important compounds in synthetic organic chemistry.
• Copper-Mediated Cyanotrifluoromethylation of Styrenes Using the Togni Reagent
  作者：Nadia O. Ilchenko、Pär G. Janson、Kálmán J. Szabó

  DOI：10.1021/jo401831t

  日期：2013.11.1

  Styrenes with an electron-deficient double bond undergo cyanotrifluoromethylation with a trifluoromethylated hypervalent iodine reagent in the presence of CuCN. The reaction proceeds under mild conditions in the presence of bulky phosphines or B(2)pin(2) additives. The process is highly regioselective and involves the consecutive formation of two C-C bonds in a single addition reaction. In the presence of a p-methoxy substituent in the styrene, oxytrifluoromethylation occurs instead of the cyanotrifluoromethylation.