2-(4-bromophenyl)-4,4,4-trifluorobutanenitrile

• 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: 2-(4-bromophenyl)-4,4,4-trifluorobutanenitrile
• 英文别名: 2-(4-Bromophenyl)-4,4,4-trifluorobutanenitrile
• 化学式: C₁₀H₇BrF₃N
• 分子量: 278.071
• InChiKey: YYFLZPDAAFJQDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 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：
  4

反应信息

• 作为产物：
  描述：

  1-(三氟甲基)-1,2-苯碘酰-3(1H)-酮 、 对溴苯乙烯 、 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72%的产率得到2-(4-bromophenyl)-4,4,4-trifluorobutanenitrile
  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

• Copper-catalyzed intermolecular cyanotrifluoromethylation of alkenes: Convenient synthesis of CF3-containing alkyl nitriles
  作者：Zhaoli Liang、Fei Wang、Pinhong Chen、Guosheng Liu

  DOI：10.1016/j.jfluchem.2014.04.004

  日期：2014.11

  A copper-catalyzed intermolecular cyanotrifluoromethylation of alkenes has been developed, in which the less reactive Togni reagent 2 was used as a CF3 source and TMSCN was employed as a cyano source. Both activated and unactivated alkenes were suitable for this transformation to give CF3-containing organonitriles under mild conditions.

  已经开发出铜催化的烯烃的分子间氰基三氟甲基化，其中反应性较低的Togni试剂2被用作CF 3源，而TMSCN被用作氰基源。活化和未活化的烯烃均适合于该转化以在温和条件下产生含CF 3的有机腈。
• 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-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.