N-methyl-p-nitrocinnamamide | 920756-27-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N-methyl-p-nitrocinnamamide
• 英文别名: N-methyl-3-(4-nitrophenyl)prop-2-enamide
• CAS: 920756-27-0
• 化学式: C₁₀H₁₀N₂O₃
• mdl: MFCD02635947
• 分子量: 206.201
• InChiKey: WDJVYCKTYBDNBF-UHFFFAOYSA-N

物化性质

• 沸点：
  412.2±37.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对硝基肉桂酸 、 盐酸甲胺 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以60%的产率得到N-methyl-p-nitrocinnamamide
  参考文献：
  名称：

  A NEW NITROGEN-TO-OXYGEN PHOSPHORYL MIGRATION

  摘要：

  The reaction of diethyl N-acetyl-N-methylphosphoramidate 1 with aldehyde in the presence of LDA at -70 degrees C results in the formation of the unstable oxyanion 6 which undergoes intramolecular rearrangement involving migration of a phosphoryl group from nitrogen to oxygen affording an amide anion 8, Subsequent proton transfer in 8 followed by elimination of phosphate anion provides the respective alpha,beta-unsaturated N-methylcarboxamide 4, The formation of considerable amounts of diethyl N-methylphosphoramidate 5 is also always observed.

  DOI：

  10.1080/10426509908037018

文献信息

• A NEW NITROGEN-TO-OXYGEN PHOSPHORYL MIGRATION
  作者：A. Koziara、A. Zwierzak

  DOI：10.1080/10426509908037018

  日期：1999.1.1

  The reaction of diethyl N-acetyl-N-methylphosphoramidate 1 with aldehyde in the presence of LDA at -70 degrees C results in the formation of the unstable oxyanion 6 which undergoes intramolecular rearrangement involving migration of a phosphoryl group from nitrogen to oxygen affording an amide anion 8, Subsequent proton transfer in 8 followed by elimination of phosphate anion provides the respective alpha,beta-unsaturated N-methylcarboxamide 4, The formation of considerable amounts of diethyl N-methylphosphoramidate 5 is also always observed.