3-Hexyl-1-iodomethyl-cyclobutanol | 217805-16-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Hexyl-1-iodomethyl-cyclobutanol
• 英文别名: 3-Hexyl-1-(iodomethyl)cyclobutan-1-ol
• CAS: 217805-16-8
• 化学式: C₁₁H₂₁IO
• 分子量: 296.192
• InChiKey: MFXXNDMICYPDLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  13
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-Hexyl-1-iodomethyl-cyclobutanol 在 三氯氧磷 作用下， 以 吡啶 为溶剂， 反应 20.0h， 以80 mg的产率得到5-Hexyl-1-oxa-spiro[2.3]hexane
  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：

  5-Hexyl-1-oxa-spiro[2.3]hexane 在 lithium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以100%的产率得到3-Hexyl-1-iodomethyl-cyclobutanol
  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