methyl 3-bromomethyl-5-tert-butylfuran-2-carboxylate | 701216-72-0

• 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 3-bromomethyl-5-tert-butylfuran-2-carboxylate
• 英文别名: Methyl 3-bromomethyl-5-t-butylfuran-2-carboxylate；methyl 3-(bromomethyl)-5-tert-butylfuran-2-carboxylate
• CAS: 701216-72-0
• 化学式: C₁₁H₁₅BrO₃
• 分子量: 275.142
• InChiKey: NBYOKVHTHICRRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 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 3-bromomethyl-5-tert-butylfuran-2-carboxylate 在 sodium hydroxide 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 16.0h， 生成 3-hydroxymethyl-5-tert-butylfuran-2-carboxylic acid
  参考文献：
  名称：

  3- and 4-Dialkoxyphosphorylmethyl Derivatives of 5-tert-Butylfuran with Electron-Withdrawing Substituents in Position 2

  摘要：

  A procedure for preparing 3- and 4-halomethyl derivatives of 5-tert-butylfuran containing electron-withdrawing substituents in position 2 was developed, and phosphorylation of the resulting products under the conditions of the Arbuzov and Michaelis-Becker reactions was studied. 3-Bromomethyl derivatives are phosphorylated with trimethyl phosphite considerably faster than their 4-chloromethyl analogs. At the same time, 3- and 4- chloromethyl derivatives of N,N-diethyl-5-tert-butylfuran-2-carboxamide under the conditions of the Michaelis-Becker reaction only slightly differ in chemical properties.

  DOI：

  10.1023/b:rugc.0000018647.14195.32
• 作为产物：
  描述：

  5-tert-butyl-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 3.0h， 以23.7 g的产率得到methyl 3-bromomethyl-5-tert-butylfuran-2-carboxylate
  参考文献：
  名称：

  3- and 4-Dialkoxyphosphorylmethyl Derivatives of 5-tert-Butylfuran with Electron-Withdrawing Substituents in Position 2

  摘要：

  A procedure for preparing 3- and 4-halomethyl derivatives of 5-tert-butylfuran containing electron-withdrawing substituents in position 2 was developed, and phosphorylation of the resulting products under the conditions of the Arbuzov and Michaelis-Becker reactions was studied. 3-Bromomethyl derivatives are phosphorylated with trimethyl phosphite considerably faster than their 4-chloromethyl analogs. At the same time, 3- and 4- chloromethyl derivatives of N,N-diethyl-5-tert-butylfuran-2-carboxamide under the conditions of the Michaelis-Becker reaction only slightly differ in chemical properties.

  DOI：

  10.1023/b:rugc.0000018647.14195.32

文献信息

• Synthesis and Phosphorylation of 2-, 3-, and 4-Halomethyl-5-tert-butylfurans
  作者：L. M. Pevzner

  DOI：10.1023/b:rugc.0000031868.97123.e1

  日期：2004.4

  Synthetic methods for preparing of 2-, 3-, and 4-halomethyl-5-tert-butylfurans are developed. It was established that the bromination of 3- and 4-methyl-2-tert-butylfurans with N-bromosuccinimide proceeds mainly at the free alpha-position of the furan ring, and not at the methyl group. Therefore, the target halomethylfurans were prepared through the corresponding 3- and 4-methoxymethyl derivatives. The obtained five products were phosphorylated with sodium diethyl phosphite under the conditions of the Michaelis-Becker reaction to give the corresponding phosphonates.