Ethyl 3-(1-ethoxyethylideneamino)benzoate | 1261298-47-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Ethyl 3-(1-ethoxyethylideneamino)benzoate
• 英文别名: ethyl 3-(1-ethoxyethylideneamino)benzoate
• CAS: 1261298-47-8
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: JEKPLCHNJVSDIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  间氨基苯甲酸 、 原乙酸三乙酯 以 甲苯 为溶剂， 反应 24.0h， 以94%的产率得到Ethyl 3-(1-ethoxyethylideneamino)benzoate
  参考文献：
  名称：

  Concurrent esterification and N-acetylation of amino acids with orthoesters: a useful reaction with interesting mechanistic implications

  摘要：

  The concurrent esterification and N-acetylation of amino acids has been studied with triethyl orthoacetate (TEOA) and triethyl orthoformate (TEOF). In a surprising finding, only 1 equiv of TEOA in refluxing toluene was necessary to convert L-proline and L-phenylalanine into the corresponding N-acetyl ethyl esters in good yield. The same transformation using TEOF was not effective. Stereochemical outcome and stoichiometric studies as well as structural variation of the amino acids in this reaction provided unexpected mechanistic insight. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.081

文献信息

• Concurrent esterification and N-acetylation of amino acids with orthoesters: a useful reaction with interesting mechanistic implications
  作者：Sarah Gibson、Dickie Romero、Hollie K. Jacobs、Aravamudan S. Gopalan

  DOI：10.1016/j.tetlet.2010.10.081

  日期：2010.12

  The concurrent esterification and N-acetylation of amino acids has been studied with triethyl orthoacetate (TEOA) and triethyl orthoformate (TEOF). In a surprising finding, only 1 equiv of TEOA in refluxing toluene was necessary to convert L-proline and L-phenylalanine into the corresponding N-acetyl ethyl esters in good yield. The same transformation using TEOF was not effective. Stereochemical outcome and stoichiometric studies as well as structural variation of the amino acids in this reaction provided unexpected mechanistic insight. (C) 2010 Elsevier Ltd. All rights reserved.