N-benzyloxy-N-phenylacrylamide | 439598-80-8

• 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: N-benzyloxy-N-phenylacrylamide
• 英文别名: N-phenyl-N-phenylmethoxyprop-2-enamide
• CAS: 439598-80-8
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: VLNJVBYVJYCBKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  环戊二烯 、 N-benzyloxy-N-phenylacrylamide 在 三异丁基铝 、 (4R,5R)-(-)-2,2-二甲基-ALPHA,ALPHA,ALPHA’,ALPHA’-四(1-萘基)-1,3-二恶烷-4,5-二甲醇 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 12.5h， 生成 exo-N-benzyloxy-N-phenylbicyclo[2.2.1]hept-5-ene-2-carboxamide 、 (R)-endo-N-benzyloxy-N-phenylbicyclo[2.2.1]-hept-5-ene-2-carboxamide 、 (S)-endo-N-benzyloxy-N-phenylbicyclo[2.2.1]hept-5-ene-2-carboxamide
  参考文献：
  名称：

  N-Alkoxyacrylamides as Substrates for Enantioselective Diels−Alder Reactions

  摘要：

  [GRAPHICS]The use of N-alkoxyacrylamides as substrates for Lewis acid catalyzed Diels-Alder reactions has been examined. Enantioselectivities up to 92% ee have been achieved using very simple chiral Lewis acids prepared from triisobutylaluminum and 2,2-dimethyl-alpha,alpha,alpha',alpha'-tetra-1-naphthalenyl-TADDOL (1-NaphtTADDOL). The use of Yamamoto's Zn-BINOL, easily prepared from Et2Zn and 1,1'-bi-2-naphthol (BINOL), proved to be even more efficient, and enantioselectivities up to 96% ee were achieved.

  DOI：

  10.1021/ol0257981
• 作为产物：
  描述：

  苯基羟胺 在 碳酸氢钠 、 potassium carbonate 作用下， 以 乙醚 、 水 、 丙酮 为溶剂， 反应 0.17h， 生成 N-benzyloxy-N-phenylacrylamide
  参考文献：
  名称：

  N-Alkoxyacrylamides as Substrates for Enantioselective Diels−Alder Reactions

  摘要：

  [GRAPHICS]The use of N-alkoxyacrylamides as substrates for Lewis acid catalyzed Diels-Alder reactions has been examined. Enantioselectivities up to 92% ee have been achieved using very simple chiral Lewis acids prepared from triisobutylaluminum and 2,2-dimethyl-alpha,alpha,alpha',alpha'-tetra-1-naphthalenyl-TADDOL (1-NaphtTADDOL). The use of Yamamoto's Zn-BINOL, easily prepared from Et2Zn and 1,1'-bi-2-naphthol (BINOL), proved to be even more efficient, and enantioselectivities up to 96% ee were achieved.

  DOI：

  10.1021/ol0257981