2-(2-Nitro-4-(trifluoromethyl)phenyl)-2-phenylpropionitrile

• 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-(2-Nitro-4-(trifluoromethyl)phenyl)-2-phenylpropionitrile
• 英文别名: 2-[2-Nitro-4-(trifluoromethyl)phenyl]-2-phenylpropanenitrile
• 化学式: C₁₆H₁₁F₃N₂O₂
• 分子量: 320.271
• InChiKey: RFQPADMFVLHYSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-氯-3-硝基三氟甲苯 、 α-甲基苯腈 在 四丁基氯化铵 sodium hydroxide 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以82%的产率得到2-(2-Nitro-4-(trifluoromethyl)phenyl)-2-phenylpropionitrile
  参考文献：
  名称：

  Does Nitroarylation of Phenylacetonitrile Proceed as a Phase-Transfer Catalyzed Process?

  摘要：

  The phase-transfer catalyzed reaction of phenylacetonitrile with 4-chloro-3-(trifluoromethyl)nitrobenzene produces 5-chloro-7-phenyl-4-(trifluoromethyl)benzisoxazole (5) not the nitroarylation product 3a as was reported by Durantini et al. (Durantini, E. N.; Chiacchiera, S. M.; Silber, J. J. J. Org. Chem. 1993, 58, 7115). The catalytic nitroarylation does not occur because the product 3a immediately forms a lipophilic carbanion which inhibits the catalytic process. The nitroarylation occurs under ion-pair extraction conditions when a stoichiometric amount of tetrabutylammonium bromide is used, whereas 2-phenylalkanenitriles are efficiently PTC nitroarylated. 4-Chloro-3-(trifluoromethyl)- and 2-chloro-5-(trifluoromethyl)nitrobenzenes enter vicarious nucleophilic substitution reactions with carbanions of chloromethyl p-tolyl sulfone. These results and formation of 5 show that carbanions add to these nitroarenes initially in positions occupied with hydrogen.

  DOI：

  10.1021/jo00122a019

文献信息

• Does Nitroarylation of Phenylacetonitrile Proceed as a Phase-Transfer Catalyzed Process?
  作者：Mieczyslaw Makosza、Alexander A. Tomashewskij

  DOI：10.1021/jo00122a019

  日期：1995.9

  The phase-transfer catalyzed reaction of phenylacetonitrile with 4-chloro-3-(trifluoromethyl)nitrobenzene produces 5-chloro-7-phenyl-4-(trifluoromethyl)benzisoxazole (5) not the nitroarylation product 3a as was reported by Durantini et al. (Durantini, E. N.; Chiacchiera, S. M.; Silber, J. J. J. Org. Chem. 1993, 58, 7115). The catalytic nitroarylation does not occur because the product 3a immediately forms a lipophilic carbanion which inhibits the catalytic process. The nitroarylation occurs under ion-pair extraction conditions when a stoichiometric amount of tetrabutylammonium bromide is used, whereas 2-phenylalkanenitriles are efficiently PTC nitroarylated. 4-Chloro-3-(trifluoromethyl)- and 2-chloro-5-(trifluoromethyl)nitrobenzenes enter vicarious nucleophilic substitution reactions with carbanions of chloromethyl p-tolyl sulfone. These results and formation of 5 show that carbanions add to these nitroarenes initially in positions occupied with hydrogen.