(2R,4R,5R)-1-aza-2-(tert-butyl)-6,8-dioxo-4,7-dimethyl-5-methoxycarbonyl-3-oxabicyclo[3.3.0]octane | 956226-90-7

• 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: (2R,4R,5R)-1-aza-2-(tert-butyl)-6,8-dioxo-4,7-dimethyl-5-methoxycarbonyl-3-oxabicyclo[3.3.0]octane
• 英文别名: methyl (1R,3R,7aR)-3-tert-butyl-1,6-dimethyl-5,7-dioxo-1,3-dihydropyrrolo[1,2-c][1,3]oxazole-7a-carboxylate
• CAS: 956226-90-7
• 化学式: C₁₄H₂₁NO₅
• 分子量: 283.324
• InChiKey: MTNFHSWSXGRYIZ-JMLUSNMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2R,4S,5R)-2-(tert-butyl)-3-(3-ethoxy-2-methyl-3-oxopropanoyl)-4-methoxycarbonyl-5-methyloxazolidine 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 3.0h， 以43%的产率得到(2R,4R,5R)-1-aza-2-(tert-butyl)-6,8-dioxo-4,7-dimethyl-5-methoxycarbonyl-3-oxabicyclo[3.3.0]octane
  参考文献：
  名称：

  Novel chiral pyrrolidinone scaffolds derived from threonine with antibacterial activity

  摘要：

  The synthesis of chiral pyrrolidinones derived from threonine, making use of a Dieckmann or aldol ring closure, is described. Compounds were found to exhibit antibacterial activity, for which the correlation with various physiochemical parameters was examined. This chiral tetramate scaffold may provide a useful template for fragment-based drug design providing rapid access to novel antibacterial compound libraries. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.064