N-(1-ethoxyethyl)-N-(4-methoxyphenyl)acetamide | 1332832-85-5

• 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: N-(1-ethoxyethyl)-N-(4-methoxyphenyl)acetamide
• CAS: 1332832-85-5
• 化学式: C₁₃H₁₉NO₃
• 分子量: 237.299
• InChiKey: RMYGKEINZPIAGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙缩醛 、 4'-甲氧基乙酰苯胺 在 三氟甲磺酸三甲基硅酯 、 N-甲基二环己基胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 以78%的产率得到N-(1-ethoxyethyl)-N-(4-methoxyphenyl)acetamide
  参考文献：
  名称：

  Synthesis of N-acyl-N,O-acetals from N-aryl amides and acetals in the presence of TMSOTf

  摘要：

  Secondary amides undergo in situ silyl imidate formation mediated by TMSOTf and an amine base, followed by addition to acetal acceptors to provide N-acyl-N,O-acetals in good yields. An analogous, high-yielding reaction is observed with 2-mercaptothiazoline as the silyl imidate precursor. Competing reduction of the acetal to the corresponding methyl ether via transfer hydrogenation can be circumvented by the replacement of CY2NMe with 2,6-lutidine under otherwise identical reaction conditions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.023

文献信息

• Synthesis of N-acyl-N,O-acetals from N-aryl amides and acetals in the presence of TMSOTf
  作者：C. Wade Downey、Alan S. Fleisher、James T. Rague、Chelsea L. Safran、Megan E. Venable、Robert D. Pike

  DOI：10.1016/j.tetlet.2011.07.023

  日期：2011.9

  Secondary amides undergo in situ silyl imidate formation mediated by TMSOTf and an amine base, followed by addition to acetal acceptors to provide N-acyl-N,O-acetals in good yields. An analogous, high-yielding reaction is observed with 2-mercaptothiazoline as the silyl imidate precursor. Competing reduction of the acetal to the corresponding methyl ether via transfer hydrogenation can be circumvented by the replacement of CY2NMe with 2,6-lutidine under otherwise identical reaction conditions. (C) 2011 Elsevier Ltd. All rights reserved.