6-(Iodomethyl)-4-oxahexanolide | 121138-09-8

• 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: 6-(Iodomethyl)-4-oxahexanolide
• 英文别名: 3-(Iodomethyl)-1,4-dioxepan-5-one
• CAS: 121138-09-8
• 化学式: C₆H₉IO₃
• 分子量: 256.04
• InChiKey: ARPGZEKVNPZQFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-烯丙氧基丙酸 在 iodonium(di-γ-collidine) perchlorate 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以25%的产率得到6-(Iodomethyl)-4-oxahexanolide
  参考文献：
  名称：

  Halocyclization of Unsaturated Alcohols and Carboxylic Acids Using Bis(sym-collidine)iodine(I) Perchlorate

  摘要：

  I（吡啶啉）与2ClO₄在室温下与不饱和醇和羧酸在二氯甲烷中反应，得到了三至七元环的碘醚和四至七元环的碘内酯，产率适中且通常具有高区域选择性。该反应特别适用于合成2-(1-碘烷基)环氧烷和环丁烷。

  DOI：

  10.1055/s-1988-27731

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.
• Preparation of seven-membered and medium-ring lactones by iodo lactonization
  作者：Bruno Simonot、Gerard Rousseau

  DOI：10.1021/jo00053a002

  日期：1993.1

  Iodo lactonization of 6-heptenoic acid using bis(sym-collidine)iodine(I) hexafluorophosphate in methylene chloride led in high yield to 6-(iodomethyl)-hexanolide while with longer omega-ethylenic carboxylic acids the corresponding lactones were obtained in low yields; however, the presence of an oxygen atom in the carbon chain allowed the formation of medium-ring iodo lactones.