methyl 5-tert-butyl-4-chloromethyl-3-methylfuran-2-carboxylate | 709674-32-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: methyl 5-tert-butyl-4-chloromethyl-3-methylfuran-2-carboxylate
• 英文别名: Methyl 5-t-butyl-4-chloromethyl-3-methyl-furan-2-carboxylate；methyl 5-tert-butyl-4-(chloromethyl)-3-methylfuran-2-carboxylate
• CAS: 709674-32-8
• 化学式: C₁₂H₁₇ClO₃
• 分子量: 244.718
• InChiKey: LIFHUOGHLYRSOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 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：

  methyl 5-tert-butyl-4-chloromethyl-3-methylfuran-2-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， 生成 methyl 5-tert-butyl-4-chloromethyl-3-(diethoxyphosphorylmethyl)furan-2-carboxylate
  参考文献：
  名称：

  Synthesis of Halomethyl Derivatives of 3- and 4-(Dialkoxyphosphorylmethyl)-5-tert-butylfuran-2-carboxylic Acid and Their Reactions with Nucleophilic Agents

  摘要：

  5-tert-Butyl-4-chloromethyl- and 5-tert-butyl-4-(diethoxyphosphorylmethyl)-3-methylfuran-2-carboxylates are effectively brominated with N-bromosuccinimide by the 3-methyl group. The bis(halomethyl) derivative is phosphorylated under conditions of the Arbuzov reaction to give the corresponding chloromethylphosphonate. The obtained organophosphorus derivatives of bromomethyl- and chloromethylfuran-2-carboxylic acid react with secondary amines and sodium butanethiolate to form the corresponding substitution products. Alkyl 5-tert-butyl-4-chloromethyl-3-(diethoxyphosphorylmethyl)-furan-2-carboxylate reacts with sodium acetate in acetic acid to give a 4-acetoxymethyl derivative. It is the first example of a facile reaction with O-nucleophiles of halomethyl derivatives of phosphonomethylated furans.

  DOI：

  10.1023/b:rugc.0000025146.10575.79
• 作为产物：
  描述：

  5-tert-butyl-3-methylfuran-2-carboxylate 、 聚合甲醛 在 盐酸 、 zinc(II) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以4.3 g的产率得到methyl 5-tert-butyl-4-chloromethyl-3-methylfuran-2-carboxylate
  参考文献：
  名称：

  Synthesis of Halomethyl Derivatives of 3- and 4-(Dialkoxyphosphorylmethyl)-5-tert-butylfuran-2-carboxylic Acid and Their Reactions with Nucleophilic Agents

  摘要：

  5-tert-Butyl-4-chloromethyl- and 5-tert-butyl-4-(diethoxyphosphorylmethyl)-3-methylfuran-2-carboxylates are effectively brominated with N-bromosuccinimide by the 3-methyl group. The bis(halomethyl) derivative is phosphorylated under conditions of the Arbuzov reaction to give the corresponding chloromethylphosphonate. The obtained organophosphorus derivatives of bromomethyl- and chloromethylfuran-2-carboxylic acid react with secondary amines and sodium butanethiolate to form the corresponding substitution products. Alkyl 5-tert-butyl-4-chloromethyl-3-(diethoxyphosphorylmethyl)-furan-2-carboxylate reacts with sodium acetate in acetic acid to give a 4-acetoxymethyl derivative. It is the first example of a facile reaction with O-nucleophiles of halomethyl derivatives of phosphonomethylated furans.

  DOI：

  10.1023/b:rugc.0000025146.10575.79