3-(1-nitroethyl)dimethylaminobenzene

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-(1-nitroethyl)dimethylaminobenzene
• 英文别名: N,N-dimethyl-3-(1-nitroethyl)aniline
• 化学式: C₁₀H₁₄N₂O₂
• 分子量: 194.233
• InChiKey: AJSVMDXNOCHZPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  硝基乙烷 、 3-溴-N,N-二甲基苯胺 在 tris(dibenzylideneacetone)dipalladium (0) caesium carbonate 、 2-二-叔丁基磷-2'-甲基联苯 作用下， 以 乙二醇二甲醚 为溶剂， 以98%的产率得到3-(1-nitroethyl)dimethylaminobenzene
  参考文献：
  名称：

  Palladium-Catalyzed Monoarylation of Nitroalkanes

  摘要：

  A general protocol for the Pd-catalyzed-arylation of nitroalkanes is described. Substituted aryl bromides as well as aryl chlorides can be coupled efficiently with a variety of nitroalkanes under mild conditions to selectively yield the monoarylated products. This method tolerates a number of functional groups including ketones, esters, and olefins. Notably, the arylation of nitroalkanes can be effected chemoselectively over ketone and ester arylation.

  DOI：

  10.1021/jo010953v

文献信息

• Palladium-catalyzed α-arylation of nitroalkanes with aryl triflates through the C(sp2)−C(sp3) bond coupling
  作者：Sengui Hu、Xiaoyu He、Zhiguo Lei、Lin Yu、Wengui Duan

  DOI：10.1016/j.molstruc.2023.135565

  日期：2023.8

  Herein, we present an efficient and practical method for the synthesis of α-arylated nitroalkanes through palladium-catalyzed cross-coupling of nitroalkanes and phenol derivatives under mild conditions. The key to this success lies in using BrettPhos as a ligand. Compared with the known methods, this method is more novel and environmentally friendly by using phenol derivatives acting as arylating reagents

  在此，我们提出了一种在温和条件下通过钯催化的硝基烷烃和苯酚衍生物的交叉偶联合成 α-芳基化硝基烷烃的有效且实用的方法。这一成功的关键在于使用 BrettPhos 作为配体。与已知方法相比，该方法使用可从天然丰富的木质素中获得的苯酚衍生物作为芳基化试剂，更加新颖和环保。带有供电子或吸电子的底物与反应相容，以 50% 至 90% 的产率提供 α-芳基化硝基烷烃。此外，可以容忍各种官能团，例如卤化物、胺、乙酰基、烯烃、酯、醚和硫醚。通过使用新开发的协议，
• Palladium-Catalyzed Monoarylation of Nitroalkanes
  作者：Erasmus M. Vogl、Stephen L. Buchwald

  DOI：10.1021/jo010953v

  日期：2002.1.1

  A general protocol for the Pd-catalyzed-arylation of nitroalkanes is described. Substituted aryl bromides as well as aryl chlorides can be coupled efficiently with a variety of nitroalkanes under mild conditions to selectively yield the monoarylated products. This method tolerates a number of functional groups including ketones, esters, and olefins. Notably, the arylation of nitroalkanes can be effected chemoselectively over ketone and ester arylation.