N-(p-chlorophenyl) trifluoroacetimidoyl iodide | 144008-07-1

• 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: N-(p-chlorophenyl) trifluoroacetimidoyl iodide
• 英文别名: N-(4-chlorophenyl)-2,2,2-trifluoroethanimidoyl iodide
• CAS: 144008-07-1
• 化学式: C₈H₄ClF₃IN
• 分子量: 333.479
• InChiKey: KDHOVGUQOAILIF-UHFFFAOYSA-N

物化性质

• 沸点：
  258.5±50.0 °C(Predicted)
• 密度：
  1.86±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 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-(p-chlorophenyl) trifluoroacetimidoyl iodide 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二(氰基苯)二氯化钯 、 三乙胺 、 对苯醌 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 C₂₀H₁₃ClF₃NO₂Se
  参考文献：
  名称：

  Heck-type coupling of intramolecularly-generated thiopalladacycles with alkenes: One pot syntheses of 3-alkenylbenzo[b]thiophenes

  摘要：

  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.

  DOI：

  10.1016/j.jorganchem.2012.02.009
• 作为产物：
  描述：

  N-(4-chlorophenyl)-2,2,2-trifluoroacetimidoyl chloride 在 sodium iodide 作用下， 以 丙酮 为溶剂， 生成 N-(p-chlorophenyl) 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

• Regioselective Synthesis of 5-Trifluoromethyl Pyrazoles by the [1+4] Cyclization of Phenylhydrazones with N-Aryl Trifluoroacetimidoyl Iodides
  作者：Hong-Bin Yu、Wei-Yuan Huang

  DOI：10.1055/s-1997-3274

  日期：1997.6

  Treatment of the phenylhydrazone of a methyl ketone (2) or cyclohexanone (3) with N-aryl trifluoroacetimidoyl iodide (1) in the presence of excess sodium hydride resulted in a [1+4] cyclization to give 5-trifluoromethyl pyrazoles (4, 5) regioselectively. The structure of products 4 or 5 was confirmed by the 13C NMR spectra.

  用过量氢化钠处理甲基酮（2）或环己酮（3）的苯肼酮与N-芳基三氟乙酰肟碘化物（1）反应，发生了[1+4]环化反应，选择性地产生5-三氟甲基吡唑（4, 5）。产品4或5的结构通过13C NMR谱得到了确认。
• 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。
• A novel route to the fluorinated diimines: carbon monoxide-promoted reductive homocoupling of fluorinated imidoyl iodides in the presence of a palladium catalyst
  作者：Hideki Amii、Mitsuhiro Kohda、Motoharu Seo、Kenji Uneyama

  DOI：10.1039/b303040g

  日期：——

  A new catalytic access to the fluorinated diimines which involves palladium(0)-catalyzed reductive dimerization of the imidoyl iodides is presented.

  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。
• (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.