N-(2,6-Dimethylphenyl)-2,2,2-trifluoroacetimidoyl iodide | 144008-09-3

• 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: N-(2,6-Dimethylphenyl)-2,2,2-trifluoroacetimidoyl iodide
• 英文别名: N-(2,6-xylyl)-2,2,2-trifluoroacetimidoyl iodide；N-(1-Iodo-2,2,2-trifluoroethylidene)-2,6-dimethylaniline；N-(2,6-dimethylphenyl)-2,2,2-trifluoroethanimidoyl iodide
• CAS: 144008-09-3
• 化学式: C₁₀H₉F₃IN
• 分子量: 327.088
• InChiKey: YQWZJPFEKLIAPA-UHFFFAOYSA-N

物化性质

• 沸点：
  277.6±50.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  N-(2,6-Dimethylphenyl)-2,2,2-trifluoroacetimidoyl iodide 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82%的产率得到2-N,3-N-bis(2,6-dimethylphenyl)-1,1,1,4,4,4-hexafluorobutane-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-(2,6-xylyl)-2,2,2-trifluoroacetimidoyl chloride 在 sodium iodide 作用下， 以 丙酮 为溶剂， 生成 N-(2,6-Dimethylphenyl)-2,2,2-trifluoroacetimidoyl iodide
  参考文献：
  名称：

  Homologation of trifluoroacetimidoyl iodides by palladium-catalyzed carbonylation. An approach to α-amino perfluoroalkanoic acids.

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)74253-5

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。
• Generation and Reaction of Metal Free Trifluoroacetimidoyl Carbanion
  作者：Kenji Uneyama、Chiemi Noritake、Keiji Sadamune

  DOI：10.1021/jo960259t

  日期：1996.1.1
• Trifluoroacetimidoyl lithium; generation and reaction with electrophiles
  作者：Hisayuki Watanabe、Fumio Yamashita、Kenji Uneyama

  DOI：10.1016/s0040-4039(00)91969-5

  日期：1993.3

  N-Aryl trifluoroacetimidoyl lithiums. synthetic equivalent of trifluoroacetyl carbanion, are prepared from N-aryl trifluoroacetimidoyl iodides by iodine-lithium exchange reaction with n-BuLi in ether at -78-degrees-C and react with various electrophiles, leading to synthetic blocks for trifluoromethylated nitrogen heterocycles.
• (Trifluoroacetimidoyl)lithiums and Their Reaction with Electrophiles
  作者：Hisayuki Watanabe、Fengyang Yan、Takashi Sakai、Kenji Uneyama

  DOI：10.1021/jo00083a016

  日期：1994.2

  N-Aryltrifluoroacetimidoyl iodides have been lithiated with n-butyllithium in ether. Because of the highly ionic nature of a carbon-lithium bond, the imidoyl carbanions are only stable below -60 degrees C. The reaction temperature, solvent, and steric bulkiness of the N-aryl substituents greatly affected alkylation. [N-(2,6-dimethylphenyl)trifluoroacetimidoyl] lithium in ether is stable enough to be alkylated and silylated on the imino carbon with electrophiles such as acyl chlorides, aldehydes, ketones, chloroformate, and trimethylsilyl chloride.