4-{[(tert-butyl)dimethylsilyl]oxy}-3-methyl-4-phenyl-1-(prop-2-enyl)azetidin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 4-{[(tert-butyl)dimethylsilyl]oxy}-3-methyl-4-phenyl-1-(prop-2-enyl)azetidin-2-one
• 英文别名: (3R,4R)-4-[tert-butyl(dimethyl)silyl]oxy-3-methyl-4-phenyl-1-prop-2-enylazetidin-2-one
• 化学式: C₁₉H₂₉NO₂Si
• 分子量: 331.53
• InChiKey: TZJJJXYRXGMNNS-HNAYVOBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-丙-2-烯基苯甲酰胺 在 六甲基磷酰三胺 、 氯化亚砜 、 2,6-二苯基苯酚 、 三甲基铝 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 9.25h， 生成 4-{[(tert-butyl)dimethylsilyl]oxy}-3-methyl-4-phenyl-1-(prop-2-enyl)azetidin-2-one
  参考文献：
  名称：

  摘要：

  We report the synthesis of N-benzyl-N-[(E)-buta-1,3-dienyl]propanamide (6) and its corresponding O-silyl-subitituted ketene N,O-acetal 7 and their Diels-Alder reaction. Propanamide G reacted smoothly, whereas the yield obtained from 7 was low, probably due to polymerization of the dienophile induced by electron transfer. The ketene N,O-acetals 27a-g were synthesized starting from the corresponding benzamides 25a-e (Scheme 9). The ketene N,O-acetals 27a-g showed increased stabilities and underwent amino-Claisen rearrangements under thermal conditions. Using catalysts, interesting side reactions leading either to the annulated systems, rac-35-37 or to a beta -lactam rac-34 were observed.

  DOI：

  10.1002/1522-2675(20001004)83:10<2712::aid-hlca2712>3.0.co;2-d

文献信息

• ——
  作者：Klaus Neuschütz、Jean-Mary Simone、Thomas Thyrann、Reinhard Neier

  DOI：10.1002/1522-2675(20001004)83:10<2712::aid-hlca2712>3.0.co;2-d

  日期：2000.10.4

  We report the synthesis of N-benzyl-N-[(E)-buta-1,3-dienyl]propanamide (6) and its corresponding O-silyl-subitituted ketene N,O-acetal 7 and their Diels-Alder reaction. Propanamide G reacted smoothly, whereas the yield obtained from 7 was low, probably due to polymerization of the dienophile induced by electron transfer. The ketene N,O-acetals 27a-g were synthesized starting from the corresponding benzamides 25a-e (Scheme 9). The ketene N,O-acetals 27a-g showed increased stabilities and underwent amino-Claisen rearrangements under thermal conditions. Using catalysts, interesting side reactions leading either to the annulated systems, rac-35-37 or to a beta -lactam rac-34 were observed.