(R)-1-(4-benzyl-2-oxooxazolidin-3-yl)octane-1,2-dione | 1092383-28-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (R)-1-(4-benzyl-2-oxooxazolidin-3-yl)octane-1,2-dione
• 英文别名: 1-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]octane-1,2-dione
• CAS: 1092383-28-2
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: BHBOAIICOLYESW-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (R)-4-Benzyl-3-oct-1-ynyl-oxazolidin-2-one 在 sodium periodate 、 ruthenium(IV) oxide hydrate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 4.0h， 以85%的产率得到(R)-1-(4-benzyl-2-oxooxazolidin-3-yl)octane-1,2-dione
  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

文献信息

• Synthesis of α-Keto-Imides via Oxidation of Ynamides
  作者：Ziyad F. Al-Rashid、Whitney L. Johnson、Richard P. Hsung、Yonggang Wei、Pei-Yuan Yao、Renhei Liu、Kang Zhao

  DOI：10.1021/jo8015067

  日期：2008.11.21

  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.