1-(2,2,2-trifluoro-1-iodoethyl)-3-hexylcyclobutane | 217805-24-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: 1-(2,2,2-trifluoro-1-iodoethyl)-3-hexylcyclobutane
• 英文别名: 1-Hexyl-3-(2,2,2-trifluoro-1-iodoethyl)cyclobutane
• CAS: 217805-24-8
• 化学式: C₁₂H₂₀F₃I
• 分子量: 348.191
• InChiKey: RVLKJRUCTZHRQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2,2,2-trifluoro-1-iodoethyl)-3-hexylcyclobutane 在 氢氧化钾 、 potassium tert-butylate 作用下， 以 乙醇 为溶剂， 反应 4.17h， 生成 (3-hexylcyclobutylidene)acetic acid
  参考文献：
  名称：

  Carbanionic Rearrangements of Halomethylenecyclobutanes. The Role of the Halogen

  摘要：

  The carbanionic ring enlargement of (halomethylene)cyclobutanes to 1-halocyclopentenes has been extended to the fluoro analogues. At 180 degrees C, 3-hexyl-1-(fluoromethylene)cyclobutane provides better yields of rearranged product than the corresponding chloride, bromide, or iodide. At temperatures < 100 degrees C, the yield of ring-enlarged product follows the order I > Br > Cl, and the fluoride does not react. Experiments with labeled substrates show that, in general, the larger the halide and the higher the reaction temperature, the greater the preference for double migration over single migration as a mechanistic pathway. The trifluormethyl group is ineffective in promoting anionic rearrangement.

  DOI：

  10.1021/jo9810866
• 作为产物：
  描述：

  三氟碘甲烷 、 1-hexyl-3-methylidenecyclobutane 在 三乙基硼 作用下， 以 正己烷 为溶剂， 反应 5.0h， 以79%的产率得到1-(2,2,2-trifluoro-1-iodoethyl)-3-hexylcyclobutane
  参考文献：
  名称：

  Carbanionic Rearrangements of Halomethylenecyclobutanes. The Role of the Halogen

  摘要：

  The carbanionic ring enlargement of (halomethylene)cyclobutanes to 1-halocyclopentenes has been extended to the fluoro analogues. At 180 degrees C, 3-hexyl-1-(fluoromethylene)cyclobutane provides better yields of rearranged product than the corresponding chloride, bromide, or iodide. At temperatures < 100 degrees C, the yield of ring-enlarged product follows the order I > Br > Cl, and the fluoride does not react. Experiments with labeled substrates show that, in general, the larger the halide and the higher the reaction temperature, the greater the preference for double migration over single migration as a mechanistic pathway. The trifluormethyl group is ineffective in promoting anionic rearrangement.

  DOI：

  10.1021/jo9810866