2-hydroxymethyl-4-bromo-5-methylfuran | 1207828-14-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 2-hydroxymethyl-4-bromo-5-methylfuran
• 英文别名: 2-Hydroxymethyl-4-bromo-5-methylfuran；(4-bromo-5-methylfuran-2-yl)methanol
• CAS: 1207828-14-5
• 化学式: C₆H₇BrO₂
• 分子量: 191.024
• InChiKey: LBOLWUVCQGQVNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  ethyl 4-bromo-5-methylfuran-2-carboxylate 在 lithium aluminium tetrahydride 、 水 、 氯化铵 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 生成 2-hydroxymethyl-4-bromo-5-methylfuran 、 5-甲基-2-呋喃甲醇
  参考文献：
  名称：

  Synthesis of isomeric bromo(diethoxyphosphorylmethyl)furans

  摘要：

  Series of the previously unknown bromo(diethoxyphosphorylmethyl)furans including four of six possible regioisomers is synthesized. The target products were obtained by bromination of the corresponding (diethoxyphosphorylmethyl)furans or by a four-step synthesis including bromination of isomeric methyl-furancarboxylates, reduction of the products formed to the corresponding alcohols, substitution of hydroxy group with halogen and phosphorylation by the Michaelis-Becker reaction. It was established for the first fime that in the course of bromination of alkyl carboxylates and phosphonates of the furan series under the typical conditions of electrophilic reaction (Br(2) + 10% molar of AlCl(3), chloroform) the substituent enters not only into the heteroring, but also into the side chain. In the case of 5-methyl-2-(diethoxyphosphorylmethyl)furan only the last reaction pathway is observed. It is shown that bromo(chloromethyl)furans react with sodium diethyl phosphite not only according to the Michaelis-Becker scheme leading to phosphonates, but also by the pathway of debromination of the furan ring. The last unexpected reaction may acquire a practical use for removing a substituent protecting the alpha-position of the furan ring under mild conditions.

  DOI：

  10.1134/s1070363209030050

文献信息

• Synthesis of isomeric bromo(diethoxyphosphorylmethyl)furans
  作者：L. M. Pevzner

  DOI：10.1134/s1070363209030050

  日期：2009.3

  Series of the previously unknown bromo(diethoxyphosphorylmethyl)furans including four of six possible regioisomers is synthesized. The target products were obtained by bromination of the corresponding (diethoxyphosphorylmethyl)furans or by a four-step synthesis including bromination of isomeric methyl-furancarboxylates, reduction of the products formed to the corresponding alcohols, substitution of hydroxy group with halogen and phosphorylation by the Michaelis-Becker reaction. It was established for the first fime that in the course of bromination of alkyl carboxylates and phosphonates of the furan series under the typical conditions of electrophilic reaction (Br(2) + 10% molar of AlCl(3), chloroform) the substituent enters not only into the heteroring, but also into the side chain. In the case of 5-methyl-2-(diethoxyphosphorylmethyl)furan only the last reaction pathway is observed. It is shown that bromo(chloromethyl)furans react with sodium diethyl phosphite not only according to the Michaelis-Becker scheme leading to phosphonates, but also by the pathway of debromination of the furan ring. The last unexpected reaction may acquire a practical use for removing a substituent protecting the alpha-position of the furan ring under mild conditions.