ethyl 2-methyl-2-nitro-5-oxohexanoate | 914379-01-4

• 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: ethyl 2-methyl-2-nitro-5-oxohexanoate
• 英文别名: ethyl (2S)-2-methyl-2-nitro-5-oxohexanoate
• CAS: 914379-01-4
• 化学式: C₉H₁₅NO₅
• 分子量: 217.222
• InChiKey: WTXFHPPAOOOAFX-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-methyl-2-nitro-5-oxohexanoate 在 palladium on activated charcoal 氢气 、 碳酸氢钠 、 sodium sulfate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， -45.0~25.0 ℃ 、334.37 kPa 条件下， 生成 tert-butyl 3-(1-cyano-2,5-dimethyl-pyrrolidin-2-yl)-3-oxo-propanoate
  参考文献：
  名称：

  Structure Reassignment and Synthesis of Jenamidines A₁/A₂, Synthesis of (+)-NP25302, and Formal Synthesis of SB-311009 Analogues

  摘要：

  and C (8-10). Jenamidines A(1)/A(2) (8) were synthesized from activated proline derivative 43 by conversion to 26 in two steps and 50% overall yield. Acylation of 26 with acid chloride 38d gave 39d, which was deprotected with TFA and then mild base to give 8 in 45% yield from 26. (-)-trans-2,5-Dimethylproline ethyl ester (49) was prepared by the enantioselective Michael reaction of ethyl 2-nitropropionate (51) and methyl vinyl ketone (50) using modified dihydroquinine 60 as the catalyst. Further elaboration converted 49 to natural (+)-NP25302 (12). A Wittig reaction of proline NCA ( 76) with ylide 79 gave 72 as a 9/1 E/Z mixture in 27% yield, completing a one-step formal synthesis of SB-311009 analogues.

  DOI：

  10.1021/jo061650+
• 作为产物：
  描述：

  丁烯酮 、 2-硝基丙酸乙酯 在 三乙烯二胺 、 chiral dihydroquinidine-based compound 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 ethyl 2-methyl-2-nitro-5-oxohexanoate 、 ethyl 2-methyl-2-nitro-5-oxohexanoate
  参考文献：
  名称：

  Structure Reassignment and Synthesis of Jenamidines A₁/A₂, Synthesis of (+)-NP25302, and Formal Synthesis of SB-311009 Analogues

  摘要：

  and C (8-10). Jenamidines A(1)/A(2) (8) were synthesized from activated proline derivative 43 by conversion to 26 in two steps and 50% overall yield. Acylation of 26 with acid chloride 38d gave 39d, which was deprotected with TFA and then mild base to give 8 in 45% yield from 26. (-)-trans-2,5-Dimethylproline ethyl ester (49) was prepared by the enantioselective Michael reaction of ethyl 2-nitropropionate (51) and methyl vinyl ketone (50) using modified dihydroquinine 60 as the catalyst. Further elaboration converted 49 to natural (+)-NP25302 (12). A Wittig reaction of proline NCA ( 76) with ylide 79 gave 72 as a 9/1 E/Z mixture in 27% yield, completing a one-step formal synthesis of SB-311009 analogues.

  DOI：

  10.1021/jo061650+