N-(2-methoxy-1-methylethyl)cinnamamide

• 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-(2-methoxy-1-methylethyl)cinnamamide
• 英文别名: N-(1-methoxypropan-2-yl)-3-phenylprop-2-enamide
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: RBUFIFMGDIRRDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  甲醇 、 1-cinnamoyl-2-methylaziridine 在 硫酸 作用下， 反应 24.0h， 生成 N-(2-methoxypropyl)cinnamamide 、 N-(2-methoxy-1-methylethyl)cinnamamide
  参考文献：
  名称：

  Aziridines. 59. Regioselectivity in nucleophilic Ring Opening of 2-Methylaziridines. Lag of bond making as model for the abnormal opening

  摘要：

  The regioselectivity ratio RS = normal : abnormal opening of activated 2-methylaziridines 2 by nucleophiles is found to range from 0.10 to unmeasurable large (only normal opening = substitution at CH2 by strongly basic carbanions). RS is assumed to result from S(N)2 variants differing in the degree to which bond breaking is ahead of bond making including perhaps synchronous S(N)2. Bond breaking will be more ahead for the N-CMe bond. High nucleophilic power pushes bond making toward a synchronous process resulting in great RS. The decrease in RS with acyl activation relative to sulfonyl activation is in accord with a flattening of the nitrogen pyramid (planarization effect). The planarization effect is retained in acidic medium by O-protonation: Rs 0.10 - 0.14 for methanolysis as compared to RS 0.43 for N-protonated sulfonylaziridine 2h. AM1 calculations support the planarization hypothesis. - No indication for SET with trityl anion was found.

  DOI：

  10.1002/prac.19933350105