2,3,5,6-Tetrafluorobenzohydroximoyl chloride | 135073-75-5

• 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: 2,3,5,6-Tetrafluorobenzohydroximoyl chloride
• 英文别名: 2,3,5,6-tetrafluoro-N-hydroxybenzenecarboximidoyl chloride
• CAS: 135073-75-5
• 化学式: C₇H₂ClF₄NO
• 分子量: 227.546
• InChiKey: RYIRXJNXGIVRLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.59
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-脱氧尿苷 、 2,3,5,6-Tetrafluorobenzohydroximoyl chloride 在 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以43%的产率得到5-(2,3,5,6-Tetrafluorobenzoyl)-2'-deoxyuridine oxime
  参考文献：
  名称：

  Reactivity of nitrile oxides toward the 5,6-double bond of uracil derivatives: synthesis of some 5-aroylpyrimidine nucleoside oximes

  摘要：

  The 5-aroylpyrimidine nucleoside oximes 3-10 were prepared in moderate to good yield by the reaction of the corresponding pyrimidine nucleosides 2a-d with stable nitrile oxides. The nitrile oxides were generated in situ from the corresponding hydroximoyl chlorides 1a-e. From these reactions, only the 1,3-addition products 3-10 were obtained. No products of cycloaddition could be isolated. The 1,3-addition products 3-10 could be formed from the ring-opening reaction of the initially formed 1,3-cycloaddition products. Evidence that supports the proposed mechanism came from experiments that used 1,3-dimethyluracil (13) as the substrate.

  DOI：

  10.1021/jo00030a011

文献信息

• The reaction or nitrile oxide with organometallic compounds
  作者：Jae Nyoung Kim、Hyoung Rae Kim、Eung K. Ryu

  DOI：10.1016/s0040-4039(00)60691-3

  日期：1993.8

  Nitrile oxides react with some organometallic compounds with or without the aid of Lewis acid depending on the organometallic nucleophiles to give oxime derivatives in good yields.

  取决于有机金属亲核试剂，在有或没有路易斯酸的帮助下，氧化腈与某些有机金属化合物反应，可得到高产率的肟衍生物。
• Lewis acid promoted electrophilic aromatic substitution reaction of nitrile oxide: Increase of the electrophilicity of carbon atom of nitrile oxide by Lewis acid complexation
  作者：Jae Nyoung Kim、Eung K. Ryu

  DOI：10.1016/s0040-4039(00)73637-9

  日期：1993.5

  Nitrile oxides complexed with Lewis acid have their increased electrophilic character at the carbon atom and could be used as hydroxynitrilium ion equivalents toward aromatic compounds.

  与路易斯酸络合的腈氧化物在碳原子上具有增强的亲电子特性，可以用作芳族化合物的羟基腈离子当量。