2,6-dimethyl-4-(2,2,2-trifluoroethyl-1-hydroxy-1-methoxycarbonyl)aniline | 128350-91-4

• 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: 2,6-dimethyl-4-(2,2,2-trifluoroethyl-1-hydroxy-1-methoxycarbonyl)aniline
• 英文别名: 4-(1-Hydroxy-1-methoxycarbonyl-2,2,2-trifluoroethyl)-2,6-dimethylaniline；methyl 2-(4-amino-3,5-dimethylphenyl)-3,3,3-trifluoro-2-hydroxypropionate；Methyl 2-(4-amino-3,5-dimethylphenyl)-3,3,3-trifluoro-2-hydroxypropanoate
• CAS: 128350-91-4
• 化学式: C₁₂H₁₄F₃NO₃
• 分子量: 277.243
• InChiKey: VRNYVGGNIPYOQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,6-dimethyl-4-(2,2,2-trifluoroethyl-1-hydroxy-1-methoxycarbonyl)aniline 、 4-氟氯苄 以 甲苯 为溶剂， 反应 1.5h， 以91%的产率得到methyl 3,3,3-trifluoro-2-[4-(4-fluorobenzylamino)-3,5-dimethylphenyl]-2-hydroxypropionate
  参考文献：
  名称：

  Trifluoromethyl-containing N-acylmethylenequinone imines as novel highly electrophilic agents

  摘要：

  The strategy of searching for highly electrophilic agents in a class of chemically inert compounds-methylenequinone imines-was developed and successfully performed. The first representative of such electrophiles -N-acyl-alpha-methoxycarbonyl-alpha-trifluoromethyl-p-methylenequinone imine 6-was synthesized. Its reactions with N-, O- and C-nucleophiles were investigated that gave various derivatives of alpha-trifluoromethyl-a-amino(oxy) acids as well as beta,beta,beta-trifluoropropionic acids. 3-Chloro-3-trifluoro-1,3-dihydroindol-2-ones were first obtained and their reactions with nucleophiles were studied with 1-aza-3-trifluoroindene-2-ones being formed as intermediates. (C) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2007.04.008
• 作为产物：
  描述：

  三氟丙酮酸甲酯 、 2,6-二甲基苯胺 生成 2,6-dimethyl-4-(2,2,2-trifluoroethyl-1-hydroxy-1-methoxycarbonyl)aniline
  参考文献：
  名称：

  Trifluoromethyl-containing N-acylmethylenequinone imines as novel highly electrophilic agents

  摘要：

  The strategy of searching for highly electrophilic agents in a class of chemically inert compounds-methylenequinone imines-was developed and successfully performed. The first representative of such electrophiles -N-acyl-alpha-methoxycarbonyl-alpha-trifluoromethyl-p-methylenequinone imine 6-was synthesized. Its reactions with N-, O- and C-nucleophiles were investigated that gave various derivatives of alpha-trifluoromethyl-a-amino(oxy) acids as well as beta,beta,beta-trifluoropropionic acids. 3-Chloro-3-trifluoro-1,3-dihydroindol-2-ones were first obtained and their reactions with nucleophiles were studied with 1-aza-3-trifluoroindene-2-ones being formed as intermediates. (C) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2007.04.008

文献信息

• Reactions of highly electrophilic polyfluorocarbonyl compounds with primary arylamines
  作者：N. D. Chkanikov、V. D. Sviridov、A. E. Zelenin、M. V. Galakhov、A. F. Kolomiets、A. V. Fokin

  DOI：10.1007/bf00960662

  日期：1990.2
• A novel three-component reaction of 1, 1-dicyano-2-(trifluoromethyl)ethylenes, primary arylamines, and ketones
  作者：V. Yu. Tyutin、N. D. Chkanikov、V. N. Nesterov、M. Yu. Antipin、Yu. T. Struchkov、A. F. Kolomiets、A. V. Fokin

  DOI：10.1007/bf00698443

  日期：1993.3

  1,1-Dicyano-2,2-bis(trifluoromethyl)ethylene and 3,3-dicyano-2-(trifluoromethyl)acrylates react with primary arylamines in the presence of ketones to form 1,1-aryl-1,4-dihydropyridine derivatives under mild conditions. The mechanism of this three-component reaction includes the formation of Schiff's bases as intermediates. 1,4-Dihydropyridine derivatives, which are the products of three-component heterocyclization, were also obtained by reaction the corresponding Schiff's bases with 1,1-dicyano-2-(trifluoromethyl)ethylenes.
• CHKANIKOV, N. D.;SVIRIDOV, V. D.;ZELENIN, A. E.;GALAXOV, M. V.;KOLOMIETS,+, IZV. AN CCCP. CEP. XIM.,(1990) N, S. 383-389
  作者：CHKANIKOV, N. D.、SVIRIDOV, V. D.、ZELENIN, A. E.、GALAXOV, M. V.、KOLOMIETS,+

  DOI：——

  日期：——
• Tjutin W. Ju., Tschkanikow N. D., Nesterow W. N., Antipin M. Ju., Strutsc+, Isw. RAN. Ser. khim., (1993) N 3, S 552-559
  作者：Tjutin W. Ju., Tschkanikow N. D., Nesterow W. N., Antipin M. Ju., Strutsc+

  DOI：——

  日期：——
• Trifluoromethyl-containing N-acylmethylenequinone imines as novel highly electrophilic agents
  作者：Victor I. Dyachenko、Aleksandr S. Peregudov、Nikolai D. Chkanikov

  DOI：10.1016/j.jfluchem.2007.04.008

  日期：2007.7

  The strategy of searching for highly electrophilic agents in a class of chemically inert compounds-methylenequinone imines-was developed and successfully performed. The first representative of such electrophiles -N-acyl-alpha-methoxycarbonyl-alpha-trifluoromethyl-p-methylenequinone imine 6-was synthesized. Its reactions with N-, O- and C-nucleophiles were investigated that gave various derivatives of alpha-trifluoromethyl-a-amino(oxy) acids as well as beta,beta,beta-trifluoropropionic acids. 3-Chloro-3-trifluoro-1,3-dihydroindol-2-ones were first obtained and their reactions with nucleophiles were studied with 1-aza-3-trifluoroindene-2-ones being formed as intermediates. (C) 2007 Elsevier B.V. All rights reserved.