ethyl 4-(chloromethyl)-5-isobutyl-2-methylfuran-3-carboxylate | 667866-82-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: ethyl 4-(chloromethyl)-5-isobutyl-2-methylfuran-3-carboxylate
• 英文别名: ethyl 4-(chloromethyl)-2-methyl-5-(2-methylpropyl)furan-3-carboxylate
• CAS: 667866-82-2
• 化学式: C₁₃H₁₉ClO₃
• 分子量: 258.745
• InChiKey: GUROEZJGPFUFEK-UHFFFAOYSA-N

物化性质

• 沸点：
  333.7±42.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 4-(chloromethyl)-5-isobutyl-2-methylfuran-3-carboxylate 在 盐酸 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 5.0h， 生成 4-Aminomethyl-5-isobutyl-2-methyl-furan-3-carboxylic acid hydrochloride
  参考文献：
  名称：

  Reactions of alkyl (halomethyl)furancarboxylates with hexamethylenetetramine

  摘要：

  All isomers of (aminomethyl)furancarboxylic acids were prepared by the Delepine reaction from alkyl (halomethyl)furancarboxylates. Treatment of the initially formed quaternary salt with an ethanolic HCl solution yielded the salts of the corresponding unstable amino acid esters. A procedure for their purification to a high degree of purity was developed. Hydrolysis of the crude esters yielded stable amino acid salts.

  DOI：

  10.1134/s1070363206080251
• 作为产物：
  描述：

  聚合甲醛 、 ethyl 5-isobutyl-2-methylfuran-3-carboxylate 在 盐酸 、 zinc(II) chloride 作用下， 以 四氯化碳 为溶剂， 以7.5 g的产率得到ethyl 4-(chloromethyl)-5-isobutyl-2-methylfuran-3-carboxylate
  参考文献：
  名称：

  摘要：

  Ethyl 5-isobutyl-2-methylfuran-3-carboxylate is selectively brominated with N-bromosuccin-imide by the methyl group to give an unstable bromide. The latter on heating or in the presence of bases undergoes dehydrobromination accompanied by rearrangement, leading to a (2,2-dimethylvinyl)furan derivative. Phosphorylation of this bromide with trimethyl phosphite gives a 2-dimethoxyphosphorylmethyl derivative and a product containing the phosphonate group alpha to the isobutyl radical. Chloromethylation of the starting ester proceeds in the 4 position of the furan ring. The resulting chloride undergoes phosphorylation under conditions of the Michaelis-Becker reaction to give the corresponding 4-(dialkoxyphosphorylmethyl)furan, and under the action of trimethyl phosphite a mixture of the same phosphonate and a dehalogenation product having a dimethylvinyl fragment. Bromination of the 4-chloromethyl derivative with N-bromosuccinimide involves the 2-methyl group. The dihalide reacts with trimethyl phosphite by way of reduction of the bromomethyl group to give 4-chloromethyl- or 4-dimethoxyphosphorylmethyl derivatives, as well as analogous dehydrohalogenation products containing a 5-dimethylvinyl fragment. A scheme describing the sequence of formation of these products in the course of the reaction is offered.

  DOI：

  10.1023/a:1024700307233