ethyl 2-(bromomethyl)-5-tert-butyl-4-(phenoxymethyl)furan-3-carboxylate | 646505-22-8

• 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 2-(bromomethyl)-5-tert-butyl-4-(phenoxymethyl)furan-3-carboxylate
• 英文别名: Ethyl 2-(bromomethyl)-5-t-butyl-4-(phenoxy-methyl)furan-3-carboxylate
• CAS: 646505-22-8
• 化学式: C₁₉H₂₃BrO₄
• 分子量: 395.293
• InChiKey: GNBHFEYUPCRYGB-UHFFFAOYSA-N

物化性质

• 沸点：
  473.4±45.0 °C(Predicted)
• 密度：
  1.285±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(bromomethyl)-5-tert-butyl-4-(phenoxymethyl)furan-3-carboxylate 、 亚磷酸三乙酯 反应 0.08h， 生成 乙基磷酸二乙酯 、
  参考文献：
  名称：

  摘要：

  Ethyl 5-tert-butyl-4-(chloromethyl)-2-methylfuran-3-carboxylate was brominated with N-bromo-succinimide to obtain the corresponding 2-bromomethyl derivative. The latter is selectively phosphorylated with trimethyl and triethyl phosphites by the bromomethyl group. The resulting [4-(chloromethyl)furyl]methyl-phosphonates in the presence of secondary amines and sodium butanethiolate behave as alkylating agents, while sodium phenolate causes their decomposition. 4-Acetoxymethyl- and 4-phenoxymethyl derivatives of the starting product are also selectively brominated with N-bromosuccinimide by the 2-methyl group. The first of the 2-(bromomethyl)furans formed is smoothly phosphorylated with trimethyl phosphite, while the second one under the action of triethyl phosphite gives a mixture of phosphorylation and debromination products. In all the cases, an additional electron-acceptor group in position 4 of alkyl 2-(bromomethyl)-5-tert-butylfuran-3-carboxylate considerably accelerates the Arbuzov reaction.

  DOI：

  10.1023/a:1024962020862
• 作为产物：
  描述：

  ethyl 5-tert-butyl-2-methyl-4-(phenoxymethyl)furan-3-carboxylate 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 1.0h， 以84%的产率得到ethyl 2-(bromomethyl)-5-tert-butyl-4-(phenoxymethyl)furan-3-carboxylate
  参考文献：
  名称：

  摘要：

  Ethyl 5-tert-butyl-4-(chloromethyl)-2-methylfuran-3-carboxylate was brominated with N-bromo-succinimide to obtain the corresponding 2-bromomethyl derivative. The latter is selectively phosphorylated with trimethyl and triethyl phosphites by the bromomethyl group. The resulting [4-(chloromethyl)furyl]methyl-phosphonates in the presence of secondary amines and sodium butanethiolate behave as alkylating agents, while sodium phenolate causes their decomposition. 4-Acetoxymethyl- and 4-phenoxymethyl derivatives of the starting product are also selectively brominated with N-bromosuccinimide by the 2-methyl group. The first of the 2-(bromomethyl)furans formed is smoothly phosphorylated with trimethyl phosphite, while the second one under the action of triethyl phosphite gives a mixture of phosphorylation and debromination products. In all the cases, an additional electron-acceptor group in position 4 of alkyl 2-(bromomethyl)-5-tert-butylfuran-3-carboxylate considerably accelerates the Arbuzov reaction.

  DOI：

  10.1023/a:1024962020862