ethyl 2-(acetoxymethyl)-5-tert-butylfuran-3-carboxylate | 442686-61-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 2-(acetoxymethyl)-5-tert-butylfuran-3-carboxylate
• 英文别名: Ethyl 2-(acetoxymethyl)-5-t-butylfuran-3-carboxylate；ethyl 2-(acetyloxymethyl)-5-tert-butylfuran-3-carboxylate
• CAS: 442686-61-5
• 化学式: C₁₄H₂₀O₅
• 分子量: 268.31
• InChiKey: FVVKJNOEBSLMSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-(acetoxymethyl)-5-tert-butylfuran-3-carboxylate 在 氢氧化钾 、 氯化亚砜 作用下， 以 水 、 苯 为溶剂， 反应 12.0h， 生成 N,N-diethyl-5-tert-butyl-2-(chloromethyl)-3-furamide
  参考文献：
  名称：

  摘要：

  2-Halomethyl derivatives of 3-functionalized 5-tert-butylfurans are phosphorylated under conditions of the Michaelis-Becker and Arbuzov reactions similarly to other halomethylfurans. No effect of the tert-butyl substituent on the yield of the reaction products was found in this case. Contrary to that, the 2-methoxymethyl derivative of 3-chloromethyl-5-tert-butylfuran proved to be more thermostable than its analog containing no tert-butyl substituent. As a result, the yield of phosphonate in the Michaelis-Becker reaction under similar conditions increases 2.5 times. The observed stabilization of the furan ring is explained by shielding of its oxygen atom by the tert-butyl group.

  DOI：

  10.1023/a:1015324824425
• 作为产物：
  描述：

  sodium acetate 、 ethyl 2-(bromomethyl)-5-tert-butylfuran-3-carboxylate 以 溶剂黄146 为溶剂， 以16.1 g的产率得到ethyl 2-(acetoxymethyl)-5-tert-butylfuran-3-carboxylate
  参考文献：
  名称：

  摘要：

  2-Halomethyl derivatives of 3-functionalized 5-tert-butylfurans are phosphorylated under conditions of the Michaelis-Becker and Arbuzov reactions similarly to other halomethylfurans. No effect of the tert-butyl substituent on the yield of the reaction products was found in this case. Contrary to that, the 2-methoxymethyl derivative of 3-chloromethyl-5-tert-butylfuran proved to be more thermostable than its analog containing no tert-butyl substituent. As a result, the yield of phosphonate in the Michaelis-Becker reaction under similar conditions increases 2.5 times. The observed stabilization of the furan ring is explained by shielding of its oxygen atom by the tert-butyl group.

  DOI：

  10.1023/a:1015324824425

文献信息

• ——
  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.