allyl 1-nitrocyclopentane-1-carboxylate | 1208267-14-4

• 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: allyl 1-nitrocyclopentane-1-carboxylate
• CAS: 1208267-14-4
• 化学式: C₉H₁₃NO₄
• 分子量: 199.207
• InChiKey: WINFYAAHCYVLOV-UHFFFAOYSA-N

物化性质

• 沸点：
  294.3±19.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.31
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  69.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  allyl 1-nitrocyclopentane-1-carboxylate 在 四(三苯基膦)钯 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以90%的产率得到1-allyl-1-nitrocyclopentane
  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

• Intercepted decarboxylative allylations of nitroalkanoates
  作者：Meghan Schmitt、Alexander J. Grenning、Jon A. Tunge

  DOI：10.1016/j.tetlet.2012.05.138

  日期：2012.8

  Using palladium-catalyzed decarboxylation, several cascade reactions of allyl and prenyl nitroalkanoates that lead to nitro-containing chemical building blocks are described. A nitronate Michael addition/Tsuji–Trost allylation cascade was developed, leading to functionally dense chemical building blocks. Likewise, a Tsuji–Trost/decarboxylative protonation sequence was developed for the synthesis of

  使用钯催化脱羧，描述了硝基链烷酸烯丙酯和异戊烯基酯的几种级联反应，这些反应产生含硝基化学结构单元。开发了硝基迈克尔加成/Tsuji-Trost烯丙基化级联，产生了功能密集的化学结构单元。同样，开发了 Tsuji-Trost/脱羧质子化序列用于合成正交官能化 2° 硝基烷烃。后一种方法可以快速接近吲哚里西啶核心。