3-(1-chloroethyl)-2,5-dimethylfuran | 943433-03-2

• 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: 3-(1-chloroethyl)-2,5-dimethylfuran
• CAS: 943433-03-2
• 化学式: C₈H₁₁ClO
• 分子量: 158.628
• InChiKey: RMNSIJOVWMCPES-UHFFFAOYSA-N

物化性质

• 沸点：
  36 °C(Press: 1 Torr)
• 密度：
  1.059±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  3-(1-chloroethyl)-2,5-dimethylfuran 、 sodium diethyl phosphite 以 苯 为溶剂， 反应 13.0h， 以27%的产率得到diethyl 1-(2,5-dimethyl-3-furyl)ethylphosphonate
  参考文献：
  名称：

  3-Chloroalkylfurans in the reaction with sodium diethyl phosphite

  摘要：

  Reduction of 3-acylfurans with lithium alumohydride in ether yields stable secondary alcohols. By treatment with thionyl chloride in the presence of pyridine, they are converted to the corresponding chlorides. 3-(1-Chloroethyl)furan and 5-methyl-3-(1-chloroethyl)furan react with sodium diethyl phosphite to give two products: 3-(1-diethoxyphosphoryiethyl)furans and 3-ethyl-2-(diethoxyphosphoryloxy)furans. The methyl group in position 5 of the furan ring increases the relative phosphate content of the mixture by a factor of approximately 2.5. Blocking of position 2 or both positions 2 and 5 of the ring with methyl groups leads to phosphonate formation only. The reaction of 2,5-dimethyl-3-(1-chloro-2-methylpropyl)furan also occurs according to the Michaelis-Becker scheme. The products of the side chain dehydrohalogenation with sodium diethyl phosphite were not found.

  DOI：

  10.1134/s107036320608024x
• 作为产物：
  描述：

  3-乙酰基-2,5-二甲基呋喃 在 吡啶 、 lithium aluminium tetrahydride 、 氯化亚砜 作用下， 以 乙醚 为溶剂， 反应 4.0h， 生成 3-(1-chloroethyl)-2,5-dimethylfuran
  参考文献：
  名称：

  3-Chloroalkylfurans in the reaction with sodium diethyl phosphite

  摘要：

  Reduction of 3-acylfurans with lithium alumohydride in ether yields stable secondary alcohols. By treatment with thionyl chloride in the presence of pyridine, they are converted to the corresponding chlorides. 3-(1-Chloroethyl)furan and 5-methyl-3-(1-chloroethyl)furan react with sodium diethyl phosphite to give two products: 3-(1-diethoxyphosphoryiethyl)furans and 3-ethyl-2-(diethoxyphosphoryloxy)furans. The methyl group in position 5 of the furan ring increases the relative phosphate content of the mixture by a factor of approximately 2.5. Blocking of position 2 or both positions 2 and 5 of the ring with methyl groups leads to phosphonate formation only. The reaction of 2,5-dimethyl-3-(1-chloro-2-methylpropyl)furan also occurs according to the Michaelis-Becker scheme. The products of the side chain dehydrohalogenation with sodium diethyl phosphite were not found.

  DOI：

  10.1134/s107036320608024x