N-benzyl-2-bromo-5-nitrobenzeneamine | 692746-94-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyl-2-bromo-5-nitrobenzeneamine
• 英文别名: N-benzyl-2-bromo-5-nitroaniline
• CAS: 692746-94-4
• 化学式: C₁₃H₁₁BrN₂O₂
• 分子量: 307.147
• InChiKey: JCYUKCGZJOABGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  丙烯酸甲酯（MA） 、 N-benzyl-2-bromo-5-nitrobenzeneamine 在 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 乙腈 为溶剂， 以60%的产率得到(E)-methyl 3-(2-(benzylamino)-4-nitrophenyl)acrylate
  参考文献：
  名称：

  Rhodium-Catalyzed Domino Conjugate Addition−Cyclization Reactions for the Synthesis of a Variety of N- and O-Heterocycles: Arylboroxines as Effective Carbon Nucleophiles

  摘要：

  Facile and efficient Rh(I)-catalyzed domino conjugate addition-cyclization reactions of olefins bearing two electrophilic sites and a pendant nucleophile with organoboroxines have been developed to afford a variety of N- and O-heterocycles, such as 3,4-dihydroquinolin-2(1H)-ones, 3,4-dihydrocoumarins, and pyrrolidin-2-ones, which constitute important motifs in biologically active natural and synthetic organic compounds.

  DOI：

  10.1021/ol100610v
• 作为产物：
  描述：

  2-溴-5-硝基苯胺 、 溴甲苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以52%的产率得到N-benzyl-2-bromo-5-nitrobenzeneamine
  参考文献：
  名称：

  Copper-catalyzed intramolecular N-arylation of ureas in water: a novel entry to benzoimidazolones

  摘要：

  The copper-catalyzed intramolecular N-arylation of 2-bromoarylureas performed in water leading to the benzo[d]imidazolone framework is reported. The scope of the methodology presented herein proved to be broad and afforded a significant number of benzoimidazolones in good to excellent yields. The reported protocol is based on the use of Cut and TMEDA acting both as the ligand and as the base in a water solution, which allows for the easy separation of the catalyst containing aqueous phase from the products by simple extraction. Additionally, the N- versus O-arylation competitive processes are also discussed. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.072

文献信息

• Synthesis of <i>N</i>‐Benzylated Anilines from the Reaction of Anilines and Benzyl Chloroformate
  作者：Hari Pati、Paul Weisbruch、Adrienne Lemon、Moses Lee

  DOI：10.1081/scc-120028366

  日期：2004.12.31

  “Bn” compounds. Reaction of aniline, 1a, gave the CBZ, or 2a, and Bn, or 3a, products in 29% and 14% yield, respectively. For 2‐nitro‐, 2‐bromo‐, and 2‐bromo‐5‐nitroanilines, the N‐benzylated compounds were produced exclusively. However, 2‐methoxy‐, 4‐bromo, 4‐iodo, and 4‐ethylanilines gave mainly CBZ products. Other compounds reported in this study gave mixtures of the two products. For 4‐chloro‐3‐nitroaniline

  摘要 氯甲酸苄酯与一系列取代苯胺的反应产生了 N-苄氧基“CBZ”产物以及意想不到的 N-苄基化“Bn”化合物。苯胺 1a 的反应分别以 29% 和 14% 的产率得到 CBZ 或 2a 和 Bn 或 3a 产物。对于 2-硝基-、2-溴-和 2-溴-5-硝基苯胺，仅生产 N-苄基化化合物。然而，2-甲氧基-、4-溴、4-碘和4-乙基苯胺主要产生CBZ产物。本研究中报道的其他化合物提供了两种产品的混合物。对于 4-氯-3-硝基苯胺，除了 Bn 和 CBZ 产物（产率分别为 53% 和 14%）外，还分离出 N,N-二苄基化产物，产率为 27%。总的来说，结果表明吸电子基团，特别是在邻位，引导了 Bn 化合物的形成，
• Copper-catalyzed intramolecular N-arylation of ureas in water: a novel entry to benzoimidazolones
  作者：Nekane Barbero、Mónica Carril、Raul SanMartin、Esther Domínguez

  DOI：10.1016/j.tet.2008.05.072

  日期：2008.7

  The copper-catalyzed intramolecular N-arylation of 2-bromoarylureas performed in water leading to the benzo[d]imidazolone framework is reported. The scope of the methodology presented herein proved to be broad and afforded a significant number of benzoimidazolones in good to excellent yields. The reported protocol is based on the use of Cut and TMEDA acting both as the ligand and as the base in a water solution, which allows for the easy separation of the catalyst containing aqueous phase from the products by simple extraction. Additionally, the N- versus O-arylation competitive processes are also discussed. (c) 2008 Elsevier Ltd. All rights reserved.
• Rhodium-Catalyzed Domino Conjugate Addition−Cyclization Reactions for the Synthesis of a Variety of <i>N</i>- and <i>O</i>-Heterocycles: Arylboroxines as Effective Carbon Nucleophiles
  作者：Ja Ock Park、So Won Youn

  DOI：10.1021/ol100610v

  日期：2010.5.21

  Facile and efficient Rh(I)-catalyzed domino conjugate addition-cyclization reactions of olefins bearing two electrophilic sites and a pendant nucleophile with organoboroxines have been developed to afford a variety of N- and O-heterocycles, such as 3,4-dihydroquinolin-2(1H)-ones, 3,4-dihydrocoumarins, and pyrrolidin-2-ones, which constitute important motifs in biologically active natural and synthetic organic compounds.