2-(5-tert-Butyl-2-ethoxymethyl-furan-3-carbonyl)-malonic acid diethyl ester | 442686-51-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(5-tert-Butyl-2-ethoxymethyl-furan-3-carbonyl)-malonic acid diethyl ester
• 英文别名: diethyl 2-[5-tert-butyl-2-(ethoxymethyl)furan-3-carbonyl]propanedioate
• CAS: 442686-51-3
• 化学式: C₁₉H₂₈O₇
• 分子量: 368.427
• InChiKey: QJSQESYZAWSCOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  92.04
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-(5-tert-Butyl-2-ethoxymethyl-furan-3-carbonyl)-malonic acid diethyl ester 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 反应 5.0h， 以1.3 g的产率得到3-acetyl-5-tert-butyl-2-(chloromethyl)furan
  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：

  ethyl 5-tert-butyl-2-(ethoxymethyl)furan-3-carboxylate 在 氢氧化钾 、 氯化亚砜 、 碘 、 magnesium 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 6.0h， 生成 2-(5-tert-Butyl-2-ethoxymethyl-furan-3-carbonyl)-malonic acid diethyl ester
  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