[5-Tert-butyl-2-(hydroxymethyl)furan-3-yl]methanol | 166758-00-5

• 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-2-(hydroxymethyl)furan-3-yl]methanol
• CAS: 166758-00-5
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: XTQPNZAVKYSGEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  53.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [5-Tert-butyl-2-(hydroxymethyl)furan-3-yl]methanol 在 吡啶 、 氯化亚砜 作用下， 以 乙醚 为溶剂， 反应 5.0h， 生成 5-Tert-butyl-2,3-bis(chloromethyl)furan
  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：

  ethyl 2-(acetoxymethyl)-5-tert-butylfuran-3-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以4.1 g的产率得到[5-Tert-butyl-2-(hydroxymethyl)furan-3-yl]methanol
  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

文献信息

• Reaction of Furan-Based o-Quinodimethanes with Triplet Oxygen. Formation of Cyclic Peroxides,1
  作者：Chin-Hsing Chou、Walter S. Trahanovsky

  DOI：10.1021/jo00122a024

  日期：1995.9

  Formation of cyclic peroxides 2a, 2b, and 2c from the reactions of 2,3-dimethylene-2,3-dihydrofuran (1a) and the 5-methyl (1b) and 5-tert-butyl (1c) derivatives with triplet oxygen is reported. Thermolysis of cyclic peroxide 2c gives dialdehyde 5, hydroxy aldehydes 6 and 7, and diol 8 as products.
• ——
  作者：L. M. Pevzner

  DOI：10.1023/a:1021605324604

  日期：——

  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.