(R,E)-methyl 4-(N-(2,3-dioxo-3-(2-oxo-4-phenyloxazolidin-3-yl)propyl)-4-methylphenylsulfonamido)but-2-enoate | 1092383-44-2

• 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: (R,E)-methyl 4-(N-(2,3-dioxo-3-(2-oxo-4-phenyloxazolidin-3-yl)propyl)-4-methylphenylsulfonamido)but-2-enoate
• 英文别名: methyl (E)-4-[[2,3-dioxo-3-[(4R)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]propyl]-(4-methylphenyl)sulfonylamino]but-2-enoate
• CAS: 1092383-44-2
• 化学式: C₂₄H₂₄N₂O₈S
• 分子量: 500.529
• InChiKey: FWKSRNMMMABTDM-ZGBFETHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  136
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (R,E)-methyl 4-(4-methyl-N-(3-(2-oxo-4-phenyloxazolidin-3-yl)prop-2-ynyl)phenylsulfonamido)but-2-enoate 在 二甲基二环氧乙烷 作用下， 以 丙酮 为溶剂， 反应 2.5h， 以46%的产率得到(R,E)-methyl 4-(N-(2,3-dioxo-3-(2-oxo-4-phenyloxazolidin-3-yl)propyl)-4-methylphenylsulfonamido)but-2-enoate
  参考文献：
  名称：

  Synthesis of α-Keto-Imides via Oxidation of Ynamides

  摘要：

  A de novo preparation of alpha-keto-imides via ynamide oxidation is described. With a number of alkyne oxidation conditions screened, a highly efficient RuO2-NaIO4 mediated oxidation and a DMDO oxidation have been identified to tolerate a wide range of ynamide types. In addition to accessing a wide variety of a-keto-imides, the RuO2-NaIO4 protocol provides a novel entry to the vicinal tricarboryl motif via oxidation of push-pull ynamides, and imido acylsilanes from silyl-substituted ynamides. Chemoselective oxidation of ynamides containing olefins can be achieved by using DMDO, while the RuO2-NaIO4 protocol is not effective. These studies provide further support for the synthetic utility of ynamides.

  DOI：

  10.1021/jo8015067