Ethyl 2-[[4-(chloromethyl)-5-methylfuran-2-carbonyl]amino]acetate | 1226017-30-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Ethyl 2-[[4-(chloromethyl)-5-methylfuran-2-carbonyl]amino]acetate
• 英文别名: ethyl 2-[[4-(chloromethyl)-5-methylfuran-2-carbonyl]amino]acetate
• CAS: 1226017-30-6
• 化学式: C₁₁H₁₄ClNO₄
• 分子量: 259.689
• InChiKey: QFUQIPUXHYWBHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 2-[[4-(chloromethyl)-5-methylfuran-2-carbonyl]amino]acetate 在 水 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 9.08h， 生成 (4-((diethoxyphosphoryl)methyl)-5-methylfuran-2-carbonyl)glycine
  参考文献：
  名称：

  Synthesis of phosphorylated derivatives of furoylglycine and furoyl-β-alanine

  摘要：

  Chloromethylfuroyl chlorides react with alkyl glycinates and beta-alanates to form the corresponding chloromethylfuroyl amides. The compounds obtained are phosphorylated with triethyl phosphite under the conditions of the Arbuzov reaction to give (diethoxyphosphorylmethylfuroyl amides. Alkaline hydrolysis of these compounds proceeds only at the carboxy group leading to (diethoxyphosphorylmethyl)furoylglycine and furoyl-beta-alanine. Selectivity of hydrolysis does not depend on the position of carboxamide and diethoxyphosphorylmethyl groups in the furan ring.

  DOI：

  10.1134/s1070363210070054
• 作为产物：
  描述：

  甘氨酸乙酯盐酸盐 、 4-(氯甲基)-5-甲基-2-糠酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.33h， 以74%的产率得到Ethyl 2-[[4-(chloromethyl)-5-methylfuran-2-carbonyl]amino]acetate
  参考文献：
  名称：

  Synthesis of phosphorylated derivatives of furoylglycine and furoyl-β-alanine

  摘要：

  Chloromethylfuroyl chlorides react with alkyl glycinates and beta-alanates to form the corresponding chloromethylfuroyl amides. The compounds obtained are phosphorylated with triethyl phosphite under the conditions of the Arbuzov reaction to give (diethoxyphosphorylmethylfuroyl amides. Alkaline hydrolysis of these compounds proceeds only at the carboxy group leading to (diethoxyphosphorylmethyl)furoylglycine and furoyl-beta-alanine. Selectivity of hydrolysis does not depend on the position of carboxamide and diethoxyphosphorylmethyl groups in the furan ring.

  DOI：

  10.1134/s1070363210070054

文献信息

• Synthesis of phosphorylated derivatives of furoylglycine and furoyl-β-alanine
  作者：L. M. Pevzner

  DOI：10.1134/s1070363210070054

  日期：2010.7

  Chloromethylfuroyl chlorides react with alkyl glycinates and beta-alanates to form the corresponding chloromethylfuroyl amides. The compounds obtained are phosphorylated with triethyl phosphite under the conditions of the Arbuzov reaction to give (diethoxyphosphorylmethylfuroyl amides. Alkaline hydrolysis of these compounds proceeds only at the carboxy group leading to (diethoxyphosphorylmethyl)furoylglycine and furoyl-beta-alanine. Selectivity of hydrolysis does not depend on the position of carboxamide and diethoxyphosphorylmethyl groups in the furan ring.