N-tert-butyl-N-methoxyacrylamide | 439598-77-3

• 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: N-tert-butyl-N-methoxyacrylamide
• 英文别名: N-tert-butyl-N-methoxyprop-2-enamide
• CAS: 439598-77-3
• 化学式: C₈H₁₅NO₂
• 分子量: 157.213
• InChiKey: DYDDDGYXQYPGCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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-tert-butyl-N-methoxyacrylamide 在 diethylzinc 、 (R)-1,1'-Bi-2-naphthol 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 exo-N-tert-butyl-N-methoxybicyclo[2.2.1]hept-5-ene-2-carboxamide 、 (R)-endo-N-tert-butyl-N-methoxybicyclo[2.2.1]hept-5-ene-2-carboxamide 、 (S)-endo-N-tert-butyl-N-methoxybicyclo[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：

  N-tert-butyl-N-hydroxyacrylamide 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以95%的产率得到N-tert-butyl-N-methoxyacrylamide
  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