Methyl 3-[1-(benzenesulfonyl)-2-oxo-3-phenylsulfanylpiperidin-3-yl]-2-[(2,2,2-trifluoroacetyl)-(2-trimethylsilylethoxymethyl)amino]propanoate | 152297-95-5

• 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: Methyl 3-[1-(benzenesulfonyl)-2-oxo-3-phenylsulfanylpiperidin-3-yl]-2-[(2,2,2-trifluoroacetyl)-(2-trimethylsilylethoxymethyl)amino]propanoate
• CAS: 152297-95-5
• 化学式: C₂₉H₃₇F₃N₂O₇S₂Si
• 分子量: 674.835
• InChiKey: HBOUYOUIMVTKGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  144
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Methyl 3-[1-(benzenesulfonyl)-2-oxo-3-phenylsulfanylpiperidin-3-yl]-2-[(2,2,2-trifluoroacetyl)-(2-trimethylsilylethoxymethyl)amino]propanoate 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到N-benzenesulfonyl-3-<2-methoxycarbonyl-2-amino>ethyl>-5,6-dihydro-2(1H)-pyridinone
  参考文献：
  名称：

  Efficient Michael Addition Reactions of the N-Arylsulfonyl-3-phenylthiopiperidones. Synthesis of 3-Substituted Dihydropyrodinnes

  摘要：

  Efficient methods for the Michael addition reactions of N-arylsulfonyl-3-phenylthiopiperidones (1) with both the protected amidoacrylates (4, 9) and the simple acrylates (12) have been developed. These reactions offer an efficient route to the 3-alkyl-substituted dihydropyridinones (3, 11), the dienophiles employed in the natural product synthesis.

  DOI：

  10.3987/com-92-s(t)117
• 作为产物：
  描述：

  methyl 2-(trifluoroacetamido)acrylate 在 双(三甲基硅烷基)氨基钾 、 silver(l) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 生成 Methyl 3-[1-(benzenesulfonyl)-2-oxo-3-phenylsulfanylpiperidin-3-yl]-2-[(2,2,2-trifluoroacetyl)-(2-trimethylsilylethoxymethyl)amino]propanoate
  参考文献：
  名称：

  Efficient Michael Addition Reactions of the N-Arylsulfonyl-3-phenylthiopiperidones. Synthesis of 3-Substituted Dihydropyrodinnes

  摘要：

  Efficient methods for the Michael addition reactions of N-arylsulfonyl-3-phenylthiopiperidones (1) with both the protected amidoacrylates (4, 9) and the simple acrylates (12) have been developed. These reactions offer an efficient route to the 3-alkyl-substituted dihydropyridinones (3, 11), the dienophiles employed in the natural product synthesis.

  DOI：

  10.3987/com-92-s(t)117

文献信息

• Efficient Michael Addition Reactions of the N-Arylsulfonyl-3-phenylthiopiperidones. Synthesis of 3-Substituted Dihydropyrodinnes
  作者：Masako Nakagawa、Yasuhiro Torisawa、Toshihiro Hosaka、Kiyoshi Tanabe、Fabric Tavet、Maki Aikawa、Tohru Hino

  DOI：10.3987/com-92-s(t)117

  日期：——

  Efficient methods for the Michael addition reactions of N-arylsulfonyl-3-phenylthiopiperidones (1) with both the protected amidoacrylates (4, 9) and the simple acrylates (12) have been developed. These reactions offer an efficient route to the 3-alkyl-substituted dihydropyridinones (3, 11), the dienophiles employed in the natural product synthesis.