Ethanimidoyl iodide, 2,2,2-trifluoro-N-(4-methylphenyl)- | 134481-25-7

• 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 iodide, 2,2,2-trifluoro-N-(4-methylphenyl)-
• 英文别名: 2,2,2-trifluoro-N-(4-methylphenyl)ethanimidoyl iodide
• CAS: 134481-25-7
• 化学式: C₉H₇F₃IN
• 分子量: 313.061
• InChiKey: MIUAEDWNOOWXMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 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：
  4

反应信息

• 作为反应物：
  描述：

  Ethanimidoyl iodide, 2,2,2-trifluoro-N-(4-methylphenyl)- 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 一氧化碳 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 70.0 ℃ 、101.32 kPa 条件下， 以70%的产率得到1,1,1,4,4,4-hexafluoro-2-N,3-N-bis(4-methylphenyl)butane-2,3-diimine
  参考文献：
  名称：

  一种制备氟化二亚胺的新途径：在钯催化剂存在下，一氧化碳促进氟化亚胺酰碘的还原均聚

  摘要：

  提出了一种新的氟化二亚胺催化途径，该途径涉及钯（0）催化的亚氨基碘化物的还原二聚。

  DOI：

  10.1039/b303040g
• 作为产物：
  描述：

  N-(4-methylphenyl)-2,2,2-trifluoroacetimidoyl chloride 在 sodium iodide 作用下， 以 丙酮 为溶剂， 以91%的产率得到Ethanimidoyl iodide, 2,2,2-trifluoro-N-(4-methylphenyl)-
  参考文献：
  名称：

  Palladium-catalyzed coupling reactions of trifluoroacetimidoyl iodides with olefins and 1-alkynes

  摘要：

  Palladium-catalyzed coupling of trifluoroacetimidoyl iodides with olefins and 1-alkynes affords trifluoromethylated alpha, beta-unsaturated imines, which are transformed into nitrogen heterocycles bearing CF3-group.

  DOI：

  10.1016/0040-4039(91)80358-d

文献信息

• Generation and Reaction of (<i>N</i>-Aryltrifluoroacetimidoyl)zinc Halide
  作者：Kenji Tamura、Fengyang Yan、Takashi Sakai、Kenji Uneyama

  DOI：10.1246/bcsj.67.300

  日期：1994.1

  (N-Aryltrifluoroacetimidoyl)zinc halides were easily generated at room temperature by the oxidative addition of imidoyl halides to activated zinc powder. [N-(2,6-Dichlorophenyl)- and N-(2,6-dimethylphenyl)trifluoroacetimidoyl]zinc halides react with aldehydes to give the corresponding alcohols smoothly in good to excellent yields. These adducts could be readily transformed to the α-amino ketones.

  (在室温下，通过将咪唑酰卤氧化加到活化锌粉中，很容易生成（N-芳基三氟乙酰亚氨酰基）卤化锌。[N-(2,6-二氯苯基)-和 N-(2,6-二甲基苯基)三氟乙酰亚氨酰基]卤化锌与醛反应，可以顺利地生成相应的醇，收率从良好到极佳。这些加合物很容易转化为 α-氨基酮。
• Synthesis of highly substituted 2-perfluoroalkyl quinolines by electrophilic iodocyclization of perfluoroalkyl propargyl imines/amines
  作者：Pravin R. Likhar、Madavu Salian Subhas、Sarabindu Roy、Mannepalli Lakshmi Kantam、Balasubramanian Sridhar、Ratanesh Kumar Seth、Sukla Biswas

  DOI：10.1039/b815398a

  日期：——

  A series of highly substituted 2-perfluoroalkyl-3-iodoquinolines are prepared by two different methods in good to excellent yields under mild reaction conditions. The first method involves iodocyclization of perfluoroalkyl propargyl imines with I2-CAN. The second method involves iodocyclization of perfluoroalkyl propargyl amines using I2 and ICl. The perfluoroalkyl propargyl amines are prepared in

  通过两种不同的方法，在温和的反应条件下，以良好或优异的收率制备了一系列高度取代的2-全氟烷基-3-碘喹啉。第一种方法涉及用I 2 -CAN对全氟烷基炔丙基亚胺进行碘环化。第二种方法涉及使用I 2和IC1对全氟烷基炔丙基胺进行碘环化。全氟烷基炔丙基胺是通过将容易获得的亚氨基碘化物与炔烃进行Sonogashira偶联，然后用NaBH 3还原而以极高的收率制备的CN。该方法的范围通过在铃木中使用所得的2-全氟烷基-3-碘喹啉，环合反应，脱卤化反应和羧化反应进行了扩展。讨论了2-全氟烷基-3-碘喹啉的抗疟活性。
• Efficient Synthesis of 2-Fluoromethylated Quinolines via Copper-Catalyzed Alkynylation and Cyclization of Fluorinated Imidoyl Iodides
  作者：Shan Li、Yafen Yuan、Jiangtao Zhu、Haibo Xie、Zixian Chen、Yongming Wu

  DOI：10.1002/adsc.201000180

  日期：——

  2‐Fluoromethylated quinolines were synthesized through the reaction of N‐aryl‐fluorinated imidoyl iodides with terminal alkynes in good yields by the catalysis of copper(I) iodide (CuI) alone.

  通过仅通过碘化铜（I）的催化使N-芳基氟化的酰亚胺基碘化物与末端炔烃以良好的产率合成2-氟甲基化的喹啉。
• Heck-type coupling of intramolecularly-generated thiopalladacycles with alkenes: One pot syntheses of 3-alkenylbenzo[b]thiophenes
  作者：Manjusha V. Karkhelikar、Shailesh S. Racharlawar、Subhas M. Salian、B. Sridhar、Pravin R. Likhar

  DOI：10.1016/j.jorganchem.2012.02.009

  日期：2012.6

  A method for stoichiometric functionalization of benzothiophene is developed by Heck-type coupling of alkenes with intramolecularly-generated thiopalladacycles obtained from palladium salts and ortho-thioanisole-substituted propargyl imines. The synthetic strategy for preparing structurally diverse 3-alkenylbenzo[b]thiophene is also extended to 3-alkenylbenzo[b]selenophenes. (C) 2012 Elsevier B. V. All rights reserved.
• Homologation of trifluoroacetimidoyl iodides by palladium-catalyzed carbonylation. An approach to α-amino perfluoroalkanoic acids.
  作者：Hisayuki Watanabe、Yoshie Hashizume、Kenji Uneyama

  DOI：10.1016/s0040-4039(00)74253-5

  日期：1992.7

  Homologation of trinuoroacetimidoyl iodides and the related perfluoro-compounds by palladium-catalyst under CO(1atm)-atmosphere in the presence of alcohols gives alpha-imino perfluoroatkanoates which are transformed to alpha-amino perfluoroalkanoic acids.