2,2,2-trifluoro-N-[2-(trifluoromethyl)phenyl]ethanimidoyl chloride | 61984-67-6

• 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: 2,2,2-trifluoro-N-[2-(trifluoromethyl)phenyl]ethanimidoyl chloride
• 英文别名: 2,2,2-trifluoro-N-(2-(trifluoromethyl)phenyl)acetimidoyl chloride；N-(2-trifluoromethylphenyl)trifluoroacetimidoyl chloride；(1Z)-2,2,2-Trifluoro-N-[2-(trifluoromethyl)phenyl]ethanimidoyl chloride
• CAS: 61984-67-6
• 化学式: C₉H₄ClF₆N
• 分子量: 275.581
• InChiKey: SFRNPQRPCXSFPZ-UHFFFAOYSA-N

物化性质

• 沸点：
  207.3±50.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoro-N-[2-(trifluoromethyl)phenyl]ethanimidoyl chloride 在 sodium azide 作用下， 以 乙腈 为溶剂， 反应 0.13h， 以97%的产率得到1-(2-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-1H-tetrazole
  参考文献：
  名称：

  Microwave-assisted synthesis of 1-aryl-5-(trifluoromethyl)-1H-tetrazoles

  摘要：

  This general protocol provides a wide variety of 5-substituted-1H-tetrazoles in good yields under mild reaction conditions. An efficient, green, and convenient method for the preparation of new 5-substituted-tetrazoles via microwave-assisted 1,3-dipolar cycloaddition reaction of N-aryl-2,2,2-trifluoroacetimidoyl chlorides and sodium azide in acetonitrile without assistance of any catalyst has been reported. The FT-IR, F-19 NMR, H-1 NMR, C-13 NMR, HMBC spectra, elemental analysis, and single-crystal X-ray analysis confirm the structures of the products. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.07.025
• 作为产物：
  描述：

  邻氨基三氟甲苯 在 四氯化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 2,2,2-trifluoro-N-[2-(trifluoromethyl)phenyl]ethanimidoyl chloride
  参考文献：
  名称：

  N-Aryl-O-glycosyl Haloacetimidates as Glycosyl Donors

  摘要：

  Reaction of 1-O-unprotected tetra-O-acetyl- and tetra-O-benzyl-glucopyranose with N-aryl haloacetimidoyl chlorides in the presence of sodium hydride and 15-crown-5 afforded N-aryl-O-glucopyranosyl haloacetimidates. Mainly the -anomers were obtained in this anomeric O-acylation-type reaction. The glycosyl donor properties of these haloacetimidates were investigated with 6-O- and 4-O-unprotected glucopyranosides as acceptors. The results were compared with those obtained with the corresponding O-glucopyranosyl trichloroacetimidates as glycosyl donors and the same acceptors. It was found that N-(2-chloro-6-methylphenyl)-O-glucopyranosyl trifluoroacetimidates (16Ad, 16Bd) exhibit glycosyl donor properties closely related to those of the corresponding N-unsubstituted O-glucopyranosyl trichloroacetimidates (12A, 12B).

  DOI：

  10.1080/07328301003597673

文献信息

• Synthesis and Photophysical Properties of 3-(Trifluoromethyl)-2H-imidazo[5,1-a]isoquinolinium Chloride Derivatives
  作者：Ali Darehkordi、Fariba Rahmani、Mahin Ramezani、Alireza Bazmandegan-Shamili

  DOI：10.1055/s-0036-1590941

  日期：2018.2

  nm with moderate to good fluorescence quantum yields. These compounds also showed high Stokes shifts, and can be used to develop ­ultrasensitive fluorescent molecular probes to study a variety of biological events and processes.

  通过异喹啉与三氟乙酰亚胺酰氯和异氰化物在干燥 CH 2 Cl 2 中的反应，以优异的产率合成了一系列新型的蓝色发光 2 H-咪唑并[5,1-a]异喹啉氯化物衍生物。荧光研究表明，这些化合物吸收紫外线辐射，然后以中等至良好的荧光量子产率发射约 481 nm 的蓝光。这些化合物还表现出高斯托克斯位移，可用于开发超灵敏荧光分子探针，以研究各种生物事件和过程。
• A Facile Synthesis of New<scp>L</scp>-Proline-Based Trifluoromethyl Oxazole Derivatives Using Microwave Irradiation and Conventional Method
  作者：Mahin Ramezani、Ali Darehkordi

  DOI：10.1002/jhet.2666

  日期：2017.3

  Cyclization reaction of l‐proline with trifluoroacetimidoyl chlorides has been developed as an efficient strategy for the synthesis of trifluoromethyl oxazole derivatives by two methods: (a) in the presence of K2CO3 as a base in acetonitrile at room temperature and (b) in the presence of K2CO3 as a base in acetonitrile using microwave irradiation, in one pot reaction. The microwave irradiation has

  的环化反应升与trifluoroacetimidoyl氯化物-脯氨酸已被开发为用于三氟甲基恶唑衍生物的合成的有效策略通过两种方法：（1）在K的存在2 CO 3在室温下和在乙腈中的碱（B）在一锅反应中，在微波辐射下，在乙腈中存在K 2 CO 3作为碱的情况下，进行微波辐射。已经发现微波辐照是最有效的方法。通过微波辐射，电子释放和吸电子取代的N-芳基三氟乙亚胺基氯衍生物均获得了高收率和较短的反应时间。
• One-pot synthesis of novel (2R,4S)-N-aryl-4-hydroxy-1-(2,2,2-trifluoroacetyl) pyrrolidine-2-carboxamides via $$\hbox {TiO}_{2}$$ TiO 2 -NPs and $$\hbox {Pd}(\hbox {PPh}_{3})_{2}\hbox {Cl}_{2}$$ Pd ( PPh 3 ) 2 Cl 2 catalysts and investigation of their biological activities
  作者：Ali Darehkordi、Mahin Ramezani

  DOI：10.1007/s11030-017-9726-y

  日期：2017.5

  AbstractA new class of (2R,4S)-N-aryl-4-hydroxy-1-(2,2,2-trifluoroacetyl)pyrrolidine-2-carboxamide compounds was synthesized by a facile one-pot reaction of trans-4-hydroxy proline and trifluoroacetimidoyl chlorides in the presence of \(\hbox TiO}_2}\)-nanoparticles as a catalyst and sodium bicarbonate as a base. Synthesized compounds showed cytotoxicity with \(\hbox IC}_50}\) values of 15.3–70

  抽象的通过反式-4-羟基的一锅反应，合成了新型的（2R，4S）-N-芳基-4-羟基-1-（2,2,2-三氟乙酰基）吡咯烷-2-羧酰胺化合物。在\（\ hbox TiO} _ 2} \）-纳米颗粒作为催化剂和碳酸氢钠作为碱的存在下，脯氨酸和三氟乙酰亚胺基氯化物。合成的化合物显示出细胞毒性，\（\ hbox中IC} _ 50} \）的15.3-70.3值 \（\ upmu \ hbox中M} \）对K562（智人，人）细胞。研究结果为一锅合成反式-4-羟基脯氨酸基N-（2,2,2-三氟乙酰化）化合物提供了一种有价值的方法。而且，这些化合物作为抗菌剂和抗真菌剂显示出显着的药物活性。 图形概要
• Telescoped, Divergent, Chemoselective C1 and C1‐C1 Homologation of Imine Surrogates: Access to Quaternary Chloro‐ and Halomethyl‐Trifluoromethyl Aziridines
  作者：Laura Ielo、Saad Touqeer、Alexander Roller、Thierry Langer、Wolfgang Holzer、Vittorio Pace

  DOI：10.1002/anie.201812525

  日期：2019.2.18

  A conceptually novel, high‐yielding, mono‐ or bis‐homologation was realized with lithium halocarbenoids and enables the one‐step, fully chemocontrolled assembly of a new class of quaternary trifluoromethyl aziridines. Trifluoroacetimidoyl chlorides (TFAICs) act as convenient electrophilic platforms, enabling the addition of either one or two homologating elements by simply controlling the stoichiometry

  卤代类胡萝卜素锂实现了概念上新颖的，高产的，单或双同系异构化，并实现了一步式，完全化学控制的新型四氟代三氟甲基氮丙啶的组装。三氟乙酰亚胺基氯（TFAIC）充当便利的亲电平台，可通过简单地控制该过程的化学计量来添加一个或两个同系元素。机理研究强调，用两种不同的类胡萝卜素（LiCH 2 Cl和LiCH 2 F）进行的同源事件导致了氟甲基类似物，其中第一个亲核试剂用于构建循环，第二个亲核试剂用于修饰所得分子结构。
• Synthesis of new α-trifluoromethyl substituted formamidines framework by using N -nucleophiles and N,S bidentate nucleophiles
  作者：Ali Darehkordi、Fariba Rahmani

  DOI：10.1016/j.jfluchem.2016.08.010

  日期：2016.10

  An efficient and convenient method for the preparation of new trifluoromethylated benzimidazole, imidazole and benzothiazole derivatives in excellent yields via reaction of N-aryl-2,2,2-trifluoroacetimidoyl chlorides with benzimidazole or benzothiazole or imidazole derivatives in the presence of NaH or NEt3 as a base in acetonitrile or THF without assistance of any catalyst has been reported. Also

  一种高效便捷的方法，可在NaH或NEt 3存在的情况下，通过N-芳基-2,2,2-三氟乙酰亚胺基氯与苯并咪唑或苯并噻唑或咪唑衍生物的反应，以优异的收率制备新的三氟甲基化苯并咪唑，咪唑和苯并噻唑衍生物。据报道，在没有任何催化剂的帮助下，在乙腈或四氢呋喃中以碱为基质。N-芳基-2,2,2-三氟乙酰亚氨基氯化物的不亲和N和S二齿亲核试剂的亲核取代也发生在N位置。FT-IR，19 F NMR，1 H NMR，13 C NMR，UV光谱和元素分析证实了产物的结构。