N-[(E)-buta-1,3-dienyl]-N-((Z)-1-{[(tert-butyl)dimethylsilyl]oxy}prop-1-enyl)benzamide | 319483-08-4

• 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-[(E)-buta-1,3-dienyl]-N-((Z)-1-{[(tert-butyl)dimethylsilyl]oxy}prop-1-enyl)benzamide
• 英文别名: N-[(1E)-buta-1,3-dienyl]-N-[(Z)-1-[tert-butyl(dimethyl)silyl]oxyprop-1-enyl]benzamide
• CAS: 319483-08-4
• 化学式: C₂₀H₂₉NO₂Si
• 分子量: 343.541
• InChiKey: OXHULCVQAVCABN-BDVCJNJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.71
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  丙烯酸甲酯（MA） 、 N-[(E)-buta-1,3-dienyl]-N-((Z)-1-{[(tert-butyl)dimethylsilyl]oxy}prop-1-enyl)benzamide 在 2,6-二叔丁基-4-甲基苯酚 作用下， 反应 149.0h， 以61%的产率得到2-[benzoyl((Z)-1-{[(tert-butyl)dimethylsilyl]oxy}prop-1-enyl)amino]cyclohex-3-ene-1-carboxylic acid methyl ester
  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
• 作为产物：
  描述：

  N-(1H-苯并三唑-1-基甲基)苯酰胺 在 N,N-二甲基丙烯基脲 、 1-甲氧基-1-(三甲基甲硅氧基)-2-甲基-1-丙烯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium hexamethyldisilazane 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 23.5h， 生成 N-[(E)-buta-1,3-dienyl]-N-((Z)-1-{[(tert-butyl)dimethylsilyl]oxy}prop-1-enyl)benzamide
  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