Ethanimidoyl chloride, 2,2,2-trifluoro-N-(3-methoxyphenyl)- | 143681-36-1

• 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: Ethanimidoyl chloride, 2,2,2-trifluoro-N-(3-methoxyphenyl)-
• 英文别名: N-(m-Anisyl)-2,2,2-trifluoroacetimidoyl chloride
• CAS: 143681-36-1
• 化学式: C₉H₇ClF₃NO
• 分子量: 237.609
• InChiKey: WUVOWVWHUFECNR-ZSOIEALJSA-N

物化性质

• 沸点：
  236.0±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)：
  3.53
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  21.59
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  Ethanimidoyl chloride, 2,2,2-trifluoro-N-(3-methoxyphenyl)- 在 氢碘酸 、 potassium carbonate 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 14.5h， 生成
  参考文献：
  名称：

  Discovery of G Protein-Biased D2 Dopamine Receptor Partial Agonists

  摘要：

  Biased ligands (also known as functionally selective ligands) of G protein-coupled receptors are valuable tools for dissecting the roles of G protein-dependent and independent signaling pathways in health and disease. Biased ligands have also been increasingly pursued by the biomedical community as promising therapeutics with improved efficacy and reduced side effects compared with unbiased ligands. We previously discovered first-in-class,beta-arrestin-biased agonists of dopamine D2 receptor (D2R) by extensively exploring multiple regions of aripiprazole, a balanced D2R agonist. In our continuing efforts to identify biased agonists of D2R, we unexpectedly discovered a G protein-biased agonist of D2R, compound 1, which is the first G protein-biased D2R agonist from the aripiprazole scaffold. We designed and synthesized novel analogues to explore two regions of 1 and conducted structure functional selectivity relationship (SFSR) studies. Here we report the discovery of 1, findings from our SFSR studies, and characterization of novel G protein-biased D2R agonists.

  DOI：

  10.1021/acs.jmedchem.6b01208
• 作为产物：
  描述：

  间氨基苯甲醚 、 三氟乙酸 在 四氯化碳 、 三乙胺 、 三苯基膦 作用下， 反应 3.0h， 以90%的产率得到Ethanimidoyl chloride, 2,2,2-trifluoro-N-(3-methoxyphenyl)-
  参考文献：
  名称：

  One-pot synthesis of trifluoroacetimidoyl halides

  摘要：

  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.

  DOI：

  10.1021/jo00053a011

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。
• Two Practical and Efficient Approaches to Fluorinated and Nonfluorinated Chiral β-Imino Sulfoxides
  作者：Santos Fustero、Antonio Navarro、Belén Pina、Amparo Asensio、Pierfrancesco Bravo、Marcello Crucianelli、Alessandro Volonterio、Matteo Zanda

  DOI：10.1021/jo980336f

  日期：1998.9.1

  Reaction of fluorinated and nonfluorinated N-substituted imidoyl chlorides 1 with lithium derivatives of enantiopure methyl p-tolyl sulfoxide 2a (or racemic methyl phenyl sulfoxide 2b) gave a wi;ie variety of chiral N-substituted beta-imino sulfoxides 4 in good to excellent yields. The title compounds (R)-4 were also prepared by aza-Wittig reaction of gamma-fluoro-beta-keto sulfoxides (R)-5 and N-aryl iminophosphoranes 6. The imino-enamino equilibrium was studied, showing, in all instances, the imino form as the predominant tautomer independent of the nature of the N-substituent. The configuration of the C=N double bond was found to be Z for both N-alkyl and N-aryl derivatives on the basis of H-1 NMR NOE difference experiments performed over several compounds. Ab initio calculations (HF/6-31G*) carried out on several representative examples of 1 and 4 are, in general, consistent with the experimental results.
• N-Substituted 2,2,2-trifluoroethanimidic acid 1-methylethylidene hydrazides as synthetic blocks for trifluoromethylated nitrogen heterocycles: syntheses and oxidative cyclizations
  作者：Kenji Uneyama、Kouji Sugimoto

  DOI：10.1021/jo00048a042

  日期：1992.10

  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.