trans-6-(Iodomethyl)-2-tert-butylhexanolide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: trans-6-(Iodomethyl)-2-tert-butylhexanolide
• 英文别名: (3S,7S)-3-tert-butyl-7-(iodomethyl)oxepan-2-one
• 化学式: C₁₁H₁₉IO₂
• 分子量: 310.175
• InChiKey: UIQPRGWPUGJLSA-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-溴-1-戊烯 在 bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 trans-6-(Iodomethyl)-2-tert-butylhexanolide
  参考文献：
  名称：

  Oxygen Effect in the Iodo Lactonization of Unsaturated Carboxylic Acids Leading to 7- to 12-Membered Ring Lactones

  摘要：

  The reaction of omega-alkenoic acids with bis(sym-collidine)iodine(I) hexafluorophosphate led to (iodomethyl) epsilon-caprolactones in good yields (49-75%) and medium ring iodo lactones in low yields (4-5%). The latter compounds have been obtained after introduction of an oxygen atom in the carbon chain. The position of the oxygen appeared important. This oxygen effect was explained by the stabilization of the intermediate iodonium ion by the oxygen atom.

  DOI：

  10.1021/jo00099a019

文献信息

• Oxygen Effect in the Iodo Lactonization of Unsaturated Carboxylic Acids Leading to 7- to 12-Membered Ring Lactones
  作者：Bruno Simonot、Gerard Rousseau

  DOI：10.1021/jo00099a019

  日期：1994.10

  The reaction of omega-alkenoic acids with bis(sym-collidine)iodine(I) hexafluorophosphate led to (iodomethyl) epsilon-caprolactones in good yields (49-75%) and medium ring iodo lactones in low yields (4-5%). The latter compounds have been obtained after introduction of an oxygen atom in the carbon chain. The position of the oxygen appeared important. This oxygen effect was explained by the stabilization of the intermediate iodonium ion by the oxygen atom.