(Z)-2,2,2-trifluoro-N-(4-fluorophenyl)acetimidoyl chloride | 364049-85-4

• 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: (Z)-2,2,2-trifluoro-N-(4-fluorophenyl)acetimidoyl chloride
• 英文别名: N-(p-Fluorophenyl)-2,2,2-trifluoroacetimidoyl chloride
• CAS: 364049-85-4
• 化学式: C₈H₄ClF₄N
• 分子量: 225.573
• InChiKey: RQMRLWLPPFJICW-AUWJEWJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  12.36
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (Z)-2,2,2-trifluoro-N-(4-fluorophenyl)acetimidoyl chloride 在 tetrabutylammonium borohydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 生成 (+)-(2S,S_S)-3,3,3-trifluoro-N-(p-fluorophenyl)-2-aminopropyl-1-(1-naphtyl)sulfoxide
  参考文献：
  名称：

  Enantioselective Synthesis of Fluorinated α-Amino Acids and Derivatives in Combination with Ring-Closing Metathesis:  Intramolecular π-Stacking Interactions as a Source of Stereocontrol

  摘要：

  [GRAPHICS]Hydride reduction of C=N bonds stereocontrolled by intramolecular m-stacking interactions of 1-naphthylsulfinyl and N-aryl groups, nonoxidative Pummerer rearrangement, and ring-closing metathesis are efficiently combined in a highly stereoselective entry to enantiomerically pure cyclic and acyclic fluorinated beta -amino alcohols and alpha -amino acid derivatives, respectively.

  DOI：

  10.1021/ol016087q
• 作为产物：
  描述：

  4-氟苯胺 、 三氟乙酸 在 三乙胺 、 三苯基膦 作用下， 以 四氯化碳 为溶剂， 以63%的产率得到(Z)-2,2,2-trifluoro-N-(4-fluorophenyl)acetimidoyl chloride
  参考文献：
  名称：

  4-CF3-ezetimibe analogs: design, synthesis, and biological evaluation of cholesterol absorption inhibitions

  摘要：

  On the purpose of looking for better cholesterol absorption inhibitors, several trifluoromethyl substituted ezetimibe analogs 1a-d were designed and synthesized. The key steps in the synthesis of these optically pure trans-4-CF3-beta-lactams include chiral auxiliary induced asymmetric hydrogenation and substrate controlled stereoselective alkylation. The inhibitory activities of these target compounds were evaluated on the cholesterol absorption in Caco-2 cells. The result showed that the inhibitory activity of compound 1a was comparable to ezetimibe. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.027

文献信息

• Synthesis of 2-trifluoromethyl-1(substituted aryl)-4(1H)-quinolones using trifluoroacetamidoyl chlorides
  作者：Simón E López、Oscar Rebollo、José Salazar、Jaime E Charris、Cicerón Yánez

  DOI：10.1016/s0022-1139(02)00288-9

  日期：2003.3

  procedure for the preparation of 2-trifluoromethyl-1(substituted aryl)-4(1H)-quinolones utilizing electrophilic trifluoroacetamidoyl chlorides as the starting materials is described. The cyclization of trifluoromethyl enaminone intermediates with potassium carbonate in hot dimethylformamide produce the trifluoromethylated 4(1H)-quinolones in good to excellent yields.

  描述了使用亲电子三氟乙酰氨基酰氯作为起始原料制备2-三氟甲基-1（取代的芳基）-4（1 H）-喹诺酮的简单两步程序。在热二甲基甲酰胺中用碳酸钾将三氟甲基烯胺酮中间体环化，可产生三氟甲基化的4（1 H）-喹诺酮，收率好至极佳。
• Process for production of 1-aryl-5-(trifluoromethyl)-1h-tetrazoles
  申请人：Hagiya Kazutake

  公开号：US20070106080A1

  公开（公告）日：2007-05-10

  The present invention relates to a process for producing an N-aryl-2,2,2-trifluoroacetimidoyl chloride represented by Formula (2): the process comprising the step of reacting in an organic solvent a tertiary amine, a 2,2,2-trifluoro-N-arylacetamide represented by Formula (1): and at least one member selected from the group consisting of phosphorus oxychloride and diphenyl chlorophosphate; and a process for producing a 1-aryl-5-(trifluoromethyl)-1H-tetrazole represented by Formula (4): the process comprising the step of reacting in an aromatic hydrocarbon solvent, in the presence of an amine salt, an N-aryl-2,2,2-trifluoroacetimidoyl chloride represented by Formula (2) shown above and an azide.

  本发明涉及一种制备由式（2）表示的N-芳基-2,2,2-三氟乙酰亚胺酰氯的方法，该方法包括在有机溶剂中反应三级胺、由式（1）表示的2,2,2-三氟-N-芳基乙酰胺和磷酰氯和二苯基氯磷酸酯等组中至少一种成员；以及制备由式（4）表示的1-芳基-5-（三氟甲基）-1H-四氮唑的方法，该方法包括在芳香族烃溶剂中反应一种胺盐、上述式（2）表示的N-芳基-2,2,2-三氟乙酰亚胺酰氯和一种偶氮化物。
• PROCESS FOR PRODUCTION OF 1-ARYL-5-(TRIFLUOROMETHYL)-1H- TETRAZOLES
  申请人：TOYO KASEI KOGYO COMPANY LIMITED

  公开号：EP1671945A1

  公开（公告）日：2006-06-21

  The present invention relates to a process for producing an N-aryl-2,2,2-trifluoroacetimidoyl chloride represented by Formula (2): the process comprising the step of reacting in an organic solvent a tertiary amine, a 2,2,2-trifluoro-N-arylacetamide represented by Formula (1): and at least one member selected from the group consisting of phosphorus oxychloride and diphenyl chlorophosphate; and a process for producing a 1-aryl-5-(trifluoromethyl)-1H-tetrazole represented by Formula (4): the process comprising the step of reacting in an aromatic hydrocarbon solvent, in the presence of an amine salt, an N-aryl-2,2,2-trifluoroacetimidoyl chloride represented by Formula (2) shown above and an azide.

  本发明涉及一种生产由式（2）表示的 N-芳基-2,2,2-三氟乙酰亚酰胺酰氯的工艺： 该工艺包括以下步骤：在有机溶剂中使叔胺和由式（1）表示的 2,2,2-三氟-N-芳基乙酰胺反应： 和至少一种选自氧氯化磷和氯磷酸二苯酯组成的组的成员；以及一种生产由式(4)代表的 1-芳基-5-(三氟甲基)-1H-四唑的工艺： 该工艺包括以下步骤：在芳香烃溶剂中，在胺盐存在下，使由上式（2）代表的 N-芳基-2,2,2-三氟乙酰亚脒酰氯和叠氮化物反应。
• One-pot synthesis of trifluoroacetimidoyl halides
  作者：Kenji Tamura、Hiromichi Mizukami、Kazuhiro Maeda、Hisayuki Watanabe、Kenji Uneyama

  DOI：10.1021/jo00053a011

  日期：1993.1

  Trifluoroacetimidoyl chlorides 1 were obtained in 80-90 % yields when a mixture of trifluoroacetic acid and a primary amine was heated in carbon tetrachloride in the presence of triphenylphosphine and triethylamine. The corresponding bromides 2 were obtained when carbon tetrabromide was used instead of carbon tetrachloride. Imidoyl iodides 3 were prepared by substitution of the chloro group of 1 by iodide ion in acetone.
• US7282609B2
  申请人：——

  公开号：US7282609B2

  公开（公告）日：2007-10-16