3-(甲氧基甲基)-5-叔丁基呋喃-2-羧酸 | 701216-82-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 中文名称: 3-(甲氧基甲基)-5-叔丁基呋喃-2-羧酸
• 英文名称: 3-(methoxymethyl)-5-tert-butylfuran-2-carboxylic acid
• 英文别名: 3-(Methoxymethyl)-5-t-butylfuran-2-carboxylic acid；5-tert-butyl-3-(methoxymethyl)furan-2-carboxylic acid
• CAS: 701216-82-2
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: XRPTUXBQVPOIHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 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：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(甲氧基甲基)-5-叔丁基呋喃-2-羧酸 在 溴 、 三苯基膦 、 copper(II) oxide 作用下， 以 喹啉 、 乙腈 、 苯 为溶剂， 反应 14.0h， 生成 3-(diethoxyphosphorylmethyl)-5-tert-butylfuran
  参考文献：
  名称：

  Synthesis and Phosphorylation of 2-, 3-, and 4-Halomethyl-5-tert-butylfurans

  摘要：

  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.

  DOI：

  10.1023/b:rugc.0000031868.97123.e1
• 作为产物：
  描述：

  methyl 3-bromomethyl-5-tert-butylfuran-2-carboxylate 在 氢氧化钾 作用下， 以 水 、 苯 为溶剂， 反应 20.0h， 生成 3-(甲氧基甲基)-5-叔丁基呋喃-2-羧酸
  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

• 3- and 4-Dialkoxyphosphorylmethyl Derivatives of 5-tert-Butylfuran with Electron-Withdrawing Substituents in Position 2
  作者：L. M. Pevzner

  DOI：10.1023/b:rugc.0000018647.14195.32

  日期：2003.11

  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.
• 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.