5-Nitro-5-prop-2-enylnonane-2,8-dione | 1208267-23-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 5-Nitro-5-prop-2-enylnonane-2,8-dione
• 英文别名: 5-nitro-5-prop-2-enylnonane-2,8-dione
• CAS: 1208267-23-5
• 化学式: C₁₂H₁₉NO₄
• 分子量: 241.287
• InChiKey: XVNUKKQRQAIRCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Nitro-5-prop-2-enylnonane-2,8-dione 在 盐酸 、 锌 、 potassium carbonate 作用下， 以 水 、 异丙醇 为溶剂， 反应 2.0h， 以99%的产率得到4-(5-Methyl-2-prop-2-enyl-3,4-dihydropyrrol-2-yl)butan-2-one
  参考文献：
  名称：

  Rapid Decarboxylative Allylation of Nitroalkanes

  摘要：

  Allyl nitroacetates undergo decarboxylative allylation to provide tertiary nitroalkanes in high yield. Moreover, the transformations are complete within several minutes under ambient conditions. High yields result because aallylation of the intermediate nitronates, which is typically problematic, is reversible under conditions of the decarboxylative allylation process. Lastly, the preparation of substrate allyl nitroacetates by tandem Knoevenagel/ Diels-Alder sequences allows the facile synthesis of relatively complex substrates that undergo diastereoselective decarboxylative allylation.

  DOI：

  10.1021/ol902828p
• 作为产物：
  描述：

  allyl 2-nitro-5-oxo-2-(3-oxobutyl)hexanoate 在 四(三苯基膦)钯 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以88%的产率得到5-Nitro-5-prop-2-enylnonane-2,8-dione
  参考文献：
  名称：

  Rapid Decarboxylative Allylation of Nitroalkanes

  摘要：

  Allyl nitroacetates undergo decarboxylative allylation to provide tertiary nitroalkanes in high yield. Moreover, the transformations are complete within several minutes under ambient conditions. High yields result because aallylation of the intermediate nitronates, which is typically problematic, is reversible under conditions of the decarboxylative allylation process. Lastly, the preparation of substrate allyl nitroacetates by tandem Knoevenagel/ Diels-Alder sequences allows the facile synthesis of relatively complex substrates that undergo diastereoselective decarboxylative allylation.

  DOI：

  10.1021/ol902828p

文献信息

• Rapid Decarboxylative Allylation of Nitroalkanes
  作者：Alexander J. Grenning、Jon A. Tunge

  DOI：10.1021/ol902828p

  日期：2010.2.19

  Allyl nitroacetates undergo decarboxylative allylation to provide tertiary nitroalkanes in high yield. Moreover, the transformations are complete within several minutes under ambient conditions. High yields result because aallylation of the intermediate nitronates, which is typically problematic, is reversible under conditions of the decarboxylative allylation process. Lastly, the preparation of substrate allyl nitroacetates by tandem Knoevenagel/ Diels-Alder sequences allows the facile synthesis of relatively complex substrates that undergo diastereoselective decarboxylative allylation.