2-(7-Octenoxy)ethanoic acid | 145147-99-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(7-Octenoxy)ethanoic acid
• 英文别名: 2-Oct-7-enoxyacetic acid
• CAS: 145147-99-5
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: TZPYAMYLVWMLFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(7-Octenoxy)ethanoic acid 在 bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以21%的产率得到10-(Iodomethyl)-3-oxadecanolide
  参考文献：
  名称：

  Preparation of seven-membered and medium-ring lactones by iodo lactonization

  摘要：

  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.

  DOI：

  10.1021/jo00053a002
• 作为产物：
  描述：

  7-辛烯-1-醇 、 溴乙酸 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以52%的产率得到2-(7-Octenoxy)ethanoic acid
  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.
• 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.