ethyl 5-(1-chloroethyl)-2-methylfuran-3-carboxylate | 1006607-97-1

• 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 5-(1-chloroethyl)-2-methylfuran-3-carboxylate
• CAS: 1006607-97-1
• 化学式: C₁₀H₁₃ClO₃
• 分子量: 216.664
• InChiKey: BXAATHLOTNFJTI-UHFFFAOYSA-N

物化性质

• 沸点：
  99-102 °C(Press: 1 Torr)
• 密度：
  1.153±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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 5-(1-chloroethyl)-2-methylfuran-3-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.42h， 生成 3-(hydroxymethyl)-2-methyl-5-vinylfuran
  参考文献：
  名称：

  Synthesis and selected reactions of ethyl 5-(1-chloroethyl)-2-methylfuran-3-carboxylate

  摘要：

  Ethyl 2-methylfuran-3-carboxylate is smoothly chloroethylated at 0 degrees C in the 5 position of the ring. The resulting halide alkylates secondary amines but eliminates HCl with sodium diethyl phosphite under the Michaelis-Becker reaction conditions and with trimethyl phosphite under the Arbuzov reaction conditions. In the reaction with sodium diethyl phosphite, small amounts of 5-[1-(diethoxyphosphoryl)ethyl]furan-3-carboxylate and 5-ethylfuran-3-carboxylate are formed. In the Arbuzov reaction at a 1 : 1.22 furan: trimethyl phosphite molar ratio, methyl 2,4-dimethyl-1-methoxy-1-oxo-l lambda(5)-1,2-dihydrophospheto[3,2-b]furan-5-carboxylate was isolated.

  DOI：

  10.1134/s107036320701015x
• 作为产物：
  描述：

  2-甲基-3-呋喃羧酸乙酯 、 乙醛 在 盐酸 、 zinc(II) chloride 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以66%的产率得到ethyl 5-(1-chloroethyl)-2-methylfuran-3-carboxylate
  参考文献：
  名称：

  Synthesis and selected reactions of ethyl 5-(1-chloroethyl)-2-methylfuran-3-carboxylate

  摘要：

  Ethyl 2-methylfuran-3-carboxylate is smoothly chloroethylated at 0 degrees C in the 5 position of the ring. The resulting halide alkylates secondary amines but eliminates HCl with sodium diethyl phosphite under the Michaelis-Becker reaction conditions and with trimethyl phosphite under the Arbuzov reaction conditions. In the reaction with sodium diethyl phosphite, small amounts of 5-[1-(diethoxyphosphoryl)ethyl]furan-3-carboxylate and 5-ethylfuran-3-carboxylate are formed. In the Arbuzov reaction at a 1 : 1.22 furan: trimethyl phosphite molar ratio, methyl 2,4-dimethyl-1-methoxy-1-oxo-l lambda(5)-1,2-dihydrophospheto[3,2-b]furan-5-carboxylate was isolated.

  DOI：

  10.1134/s107036320701015x