2-isobutyl-4-chloromethylfuran | 160891-68-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-isobutyl-4-chloromethylfuran
• 英文别名: 4-(chloromethyl)-2-(2-methylpropyl)furan
• CAS: 160891-68-9
• 化学式: C₉H₁₃ClO
• 分子量: 172.655
• InChiKey: OYNPNWYIYAKBCO-UHFFFAOYSA-N

物化性质

• 沸点：
  56 °C(Press: 1 Torr)
• 密度：
  1.039±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-isobutyl-4-chloromethylfuran 以 乙腈 、 苯 为溶剂， 反应 21.0h， 生成 2-isobutyl-4-diethoxyphosphorylmethyl-5-(dimethylaminomethyl)furan hydrochloride
  参考文献：
  名称：

  Synthesis and aminomethylation of 2-isobutyl-3-and 4-diethoxyphosphorylmethylfurans

  摘要：

  Synthetic procedure for preparing 2-isobutyl-3- and 4-furancarboxylic acyl chlorides is developed. Reduction of these compounds with lithium alumohydride leads to corresponding alcohols which under treating with thionyl chloride in the presence of pyridine form chloromethyl derivatives. The latter compounds are phosphorylated with sodium diethyl phosphite under the Michaelis-Becker reaction conditions to give corresponding phosphonates. Reaction of compounds obtained with dimethyl(chloromethyl)amine proceeds at the free alpha-position of the furan ring and delivers aminophosphonates. These substances do not evolve dimethylamine even under the conditions of vacuum distillation (145-150 degrees C, 1 mm Hg).

  DOI：

  10.1134/s1070363206070103
• 作为产物：
  描述：

  2-isobutyl-4-chloroformylfuran 在 吡啶 、 lithium aluminium tetrahydride 、 氯化亚砜 作用下， 以 乙醚 为溶剂， 反应 5.0h， 生成 2-isobutyl-4-chloromethylfuran
  参考文献：
  名称：

  Synthesis and aminomethylation of 2-isobutyl-3-and 4-diethoxyphosphorylmethylfurans

  摘要：

  Synthetic procedure for preparing 2-isobutyl-3- and 4-furancarboxylic acyl chlorides is developed. Reduction of these compounds with lithium alumohydride leads to corresponding alcohols which under treating with thionyl chloride in the presence of pyridine form chloromethyl derivatives. The latter compounds are phosphorylated with sodium diethyl phosphite under the Michaelis-Becker reaction conditions to give corresponding phosphonates. Reaction of compounds obtained with dimethyl(chloromethyl)amine proceeds at the free alpha-position of the furan ring and delivers aminophosphonates. These substances do not evolve dimethylamine even under the conditions of vacuum distillation (145-150 degrees C, 1 mm Hg).

  DOI：

  10.1134/s1070363206070103