(R,E)-methyl 6-oxo-8-(2-oxo-4-phenyloxazolidin-3-yl)oct-2-en-7-ynoate | 1092383-41-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R,E)-methyl 6-oxo-8-(2-oxo-4-phenyloxazolidin-3-yl)oct-2-en-7-ynoate
• CAS: 1092383-41-9
• 化学式: C₁₈H₁₇NO₅
• 分子量: 327.337
• InChiKey: QBPSUDPPVUGQHI-DHINHOHASA-N

反应信息

• 作为反应物：
  描述：

  (R,E)-methyl 6-oxo-8-(2-oxo-4-phenyloxazolidin-3-yl)oct-2-en-7-ynoate 在 二甲基二环氧乙烷 作用下， 以 丙酮 为溶剂， 反应 2.5h， 以65%的产率得到(R,E)-methyl 6,7,8-trioxo-8-(2-oxo-4-phenyloxazolidin-3-yl)oct-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