2,2,2-trifluoro-N-naphthalen-1-ylethanimidoyl chloride | 143681-37-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,2,2-trifluoro-N-naphthalen-1-ylethanimidoyl chloride
• 英文别名: (1Z)-2,2,2-trifluoro-N-(naphtalen-1-yl)ethanimidoyl chloride；N-Naphthyl-2,2,2-trifluoroacetimidoyl chloride
• CAS: 143681-37-2
• 化学式: C₁₂H₇ClF₃N
• 分子量: 257.642
• InChiKey: WMYIMHCLYPBXPC-BOPFTXTBSA-N

物化性质

• 沸点：
  288.3±50.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  2,2,2-trifluoro-N-naphthalen-1-ylethanimidoyl chloride 在 次氯酸叔丁酯 、 一水合肼 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 3-(trifluoromethyl)naphtho-1,2,4-triazine
  参考文献：
  名称：

  N-Substituted 2,2,2-trifluoroethanimidic acid 1-methylethylidene hydrazides as synthetic blocks for trifluoromethylated nitrogen heterocycles: syntheses and oxidative cyclizations

  摘要：

  N-Substituted 2,2,2-trifluoroethanimidic acid 1-methylethylidene hydrazides have been prepared and allowed to react with tert-butyl hypochlorite in CH2Cl2. N-Aryl-, N-alkyl-, and N-(methoxycarbonyl)amidrazones 2-4 undergo three types of cyclizations via the initially formed N-chloro intermediates leading to 3-(trifluoromethyl)-1,2,4-benzotriazines, 5, 3-(trifluoromethyl)-5-alkyltriazoles 8 and 9, and 3-chloro-3-(trifluoromethyl)-4-N-(methoxycarbonyl)-5,5-dimethyltriazoline (11), respectively. Reaction mechanisms for the cyclizations are discussed.

  DOI：

  10.1021/jo00048a042
• 作为产物：
  描述：

  1-萘胺 、 三氟乙酸 在 四氯化碳 、 三乙胺 、 三苯基膦 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.17h， 生成 2,2,2-trifluoro-N-naphthalen-1-ylethanimidoyl chloride
  参考文献：
  名称：

  亚胺代孕酯在锂类胡萝卜素介导的同源物中的卤素赋予反应性：双三氟甲基β-二酮的直接组装和LiCH2I的双重作用

  摘要：

  报道了桥接两个三氟乙酰氨基酰氯（TFAICs）单元的碳单元的选择性形式插入（同源）。该策略基于高度化学选择性的同源性-金属化-酰基亲核取代序列，该序列可精确地在一次合成操作中组装出新颖的三氟甲基化β-二酮。与以前使用LiCH 2 Cl制备氮丙啶的同系物不同，本文我们利用碘甲基锂独特的能力同时充当C1源（增效作用）和金属化剂。基于实验证据的机械原理支持了该假设的提议，并且结构分析收集了催化中这类有价值的配体的关键方面。

  DOI：

  10.1002/anie.202007954

文献信息

• 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.
• Enantioselective Synthesis of Fluorinated α-Amino Acids and Derivatives in Combination with Ring-Closing Metathesis:  Intramolecular π-Stacking Interactions as a Source of Stereocontrol
  作者：Santos Fustero、Antonio Navarro、Belén Pina、Juan García Soler、Ana Bartolomé,、Amparo Asensio、Antonio Simón、Pierfrancesco Bravo、Giovanni Fronza、Alessandro Volonterio、Matteo Zanda

  DOI：10.1021/ol016087q

  日期：2001.8.1

  [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.
• US7282609B2
  申请人：——

  公开号：US7282609B2

  公开（公告）日：2007-10-16