5-tert-butyl-3-chloromethyl-4-ethoxymethyl-2-methylfuran | 510773-73-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 5-tert-butyl-3-chloromethyl-4-ethoxymethyl-2-methylfuran
• 英文别名: 5-t-Butyl-3-chloromethyl-4-ethoxymethyl-2-methylfuran；2-tert-butyl-4-(chloromethyl)-3-(ethoxymethyl)-5-methylfuran
• CAS: 510773-73-6
• 化学式: C₁₃H₂₁ClO₂
• 分子量: 244.762
• InChiKey: OFTSIMLNGLGMSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  sodium diethyl phosphite 、 5-tert-butyl-3-chloromethyl-4-ethoxymethyl-2-methylfuran 以 苯 为溶剂， 反应 9.0h， 以45%的产率得到5-tert-butyl-3-(diethoxyphosphorylmethyl)-4-ethoxymethyl-2-methylfuran
  参考文献：
  名称：

  摘要：

  Reduction of 2- and 4-acetoxymethyl derivatives of 5-tert-butylfuran-3-carboxylic acid leads to the corresponding bis(hydroxymethyl)furans. Bis(chloromethyl)furans prepared from the latter were involved in reaction with sodium diethyl phosphite. In the presence of two equivalents of a phosphorus-containing nucleophile, bis(phosphonomethyl)furans are formed. One equivalent of sodium diethyl phosphite reacts with 3,4-bis(chloromethyl)furan to give a mixture of 3-and 4-phosphorylated products in a 4.5:1 ratio in a low yield. The revealed difference in reactivity between the 3- and 4-chloromethyl groups demonstrates the importance of shielding of the chloromethyl group by the neighboring tert-butyl substituent. Examination of the H-1 NMR spectra of 3,4-bis(hydroxymethyl)-, 3,4-bis(chloromethyl)-, 3,4-bis(diethoxyphosphorylmethyl)5-tert-butylfurans, and also specially prepared 5-tert-butyl-3-(diethoxyphosphorylmethyl)-4-(ethoxymethyl)-2-methylfuran established that the signal of the substituent neighboring to the tert-butyl group is always shifted downfield.

  DOI：

  10.1023/a:1021605324604
• 作为产物：
  描述：

  5-tert-butyl-4-ethoxymethyl-3-hydroxymethyl-2-methylfuran 在 吡啶 、 氯化亚砜 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以2.2 g的产率得到5-tert-butyl-3-chloromethyl-4-ethoxymethyl-2-methylfuran
  参考文献：
  名称：

  摘要：

  Reduction of 2- and 4-acetoxymethyl derivatives of 5-tert-butylfuran-3-carboxylic acid leads to the corresponding bis(hydroxymethyl)furans. Bis(chloromethyl)furans prepared from the latter were involved in reaction with sodium diethyl phosphite. In the presence of two equivalents of a phosphorus-containing nucleophile, bis(phosphonomethyl)furans are formed. One equivalent of sodium diethyl phosphite reacts with 3,4-bis(chloromethyl)furan to give a mixture of 3-and 4-phosphorylated products in a 4.5:1 ratio in a low yield. The revealed difference in reactivity between the 3- and 4-chloromethyl groups demonstrates the importance of shielding of the chloromethyl group by the neighboring tert-butyl substituent. Examination of the H-1 NMR spectra of 3,4-bis(hydroxymethyl)-, 3,4-bis(chloromethyl)-, 3,4-bis(diethoxyphosphorylmethyl)5-tert-butylfurans, and also specially prepared 5-tert-butyl-3-(diethoxyphosphorylmethyl)-4-(ethoxymethyl)-2-methylfuran established that the signal of the substituent neighboring to the tert-butyl group is always shifted downfield.

  DOI：

  10.1023/a:1021605324604