N-benzyl-2-bromo-4-fluorobenzeneamine | 1016170-26-5

• 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-4-fluorobenzeneamine
• 英文别名: benzyl-(2-bromo-4-fluorophenyl)amine；N-benzyl-2-bromo-4-fluoroaniline
• CAS: 1016170-26-5
• 化学式: C₁₃H₁₁BrFN
• 分子量: 280.139
• InChiKey: ZYWNARZUNLGHGH-UHFFFAOYSA-N

物化性质

• 沸点：
  348.0±37.0 °C(Predicted)
• 密度：
  1.474±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 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：
  12
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyl-2-bromo-4-fluorobenzeneamine 在 2-双环己基膦-2',6'-二甲氧基联苯 、 dipotassium peroxodisulfate 、 palladium diacetate 、 caesium carbonate 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 16.0h， 生成 6-fluoro-1-(3-nitrophenyl)-2-phenyl-1H-benzo[d]imidazole
  参考文献：
  名称：

  Sulfate Radical Anion (SO₄^•–) Mediated C(sp³)–H Nitrogenation/Oxygenation in N-Aryl Benzylic Amines Expanded the Scope for the Synthesis of Benzamidine/Oxazine Heterocycles

  摘要：

  A transition-metal-free, K2S2O8-mediated intra-molecular, oxidative nitrogenation/oxygenation of C(sp(3))-H in N-aryl benzylic amines followed by oxidation at the benzylic center has been developed for the synthesis of benzamidine/benzoxazine heterocycles, providing an expedient access to quinazolin-4(3H)-ones, N-aryl-2-arylbenzimidazoles, and 4H-3,1-benzoxazin-4-ones. A considerable amount of work dealing with the mechanistic study to understand the crucial intramolecular cyclization step largely favors an iminium ion as the key intermediate.

  DOI：

  10.1021/acs.joc.5b01872
• 作为产物：
  描述：

  (2-Bromo-4-fluoro-phenyl)-[1-phenyl-meth-(E)-ylidene]-amine 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 N-benzyl-2-bromo-4-fluorobenzeneamine
  参考文献：
  名称：

  Influence of intramolecular coordination on the transmissability of a bridging Hg-N group

  摘要：

  DOI：

  10.1007/bf00948068

文献信息

• Asymmetric Cascade Reaction Sequences via Chiral Lithiated Intermediates
  作者：Anne-Marie L. Hogan、Donal F. O'Shea

  DOI：10.1021/jo702290f

  日期：2008.4.1

  generation of chiral lithiated intermediates which have broad synthetic potential. These intermediates have been exploited in a series of further in situ reactions with electrophiles to generate a collection of products each containing a common stereogenic center. The stereogenic center, formed in high enantiomeric ratio in the first carbolithiation step, is carried through the cascade reaction sequence

  该（ - ） -的金雀花碱介导的对映选择性分子间碳锂（ē）-2-丙烯基芳基胺可以产生具有广泛合成潜力的手性锂化中间体。这些中间体已在与亲电试剂的一系列其他原位反应中得到利用，以生成一系列产物，每个产物均包含一个共同的立体异构中心。在第一步碳烷化步骤中以高对映体比例形成的立体异构中心通过级联反应序列传递至最终产物，并且与所用的亲电子试剂无关。该方法通过合成结构多样的手性苯胺，吲哚和吲哚酮以证明其er均为92：8（±1）。杂环合成涉及对映选择性烯烃碳环化，以及随后用合适的亲电试剂捕获中间有机锂，
• One-pot strategy of copper-catalyzed synthesis of 1,2-disubstituted benzimidazoles
  作者：Caixia Xie、Xushuang Han、Jian Gong、Danyang Li、Chen Ma

  DOI：10.1039/c7ob00945c

  日期：——

  A simple, one-pot and copper-catalyzed coupling reaction for the construction of 1,2-disubstituted benzimidazole derivatives is described. Low-cost copper salt and weak base K3PO4 were utlized in this reaction. A variety of 1,2-disubstituted benzimidazoles were obtained in moderate to excellent yields.

  描述了一种简单的，一锅法和铜催化的偶联反应，用于构建1,2-二取代的苯并咪唑衍生物。在该反应中使用了廉价的铜盐和弱碱K3PO4。以中等至优异的产率获得了各种1,2-二取代的苯并咪唑。
• 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.
• Influence of intramolecular coordination on the transmissability of a bridging Hg-N group
  作者：S. I. Pombrik、E. V. Polunkin、A. S. Peregudov、�. I. Fedin、D. N. Kravtsov

  DOI：10.1007/bf00948068

  日期：1985.4
• Sulfate Radical Anion (SO₄^•–) Mediated C(sp³)–H Nitrogenation/Oxygenation in <i>N</i>-Aryl Benzylic Amines Expanded the Scope for the Synthesis of Benzamidine/Oxazine Heterocycles
  作者：Joydev K. Laha、K. S. Satyanarayana Tummalapalli、Akshay Nair、Nidhi Patel

  DOI：10.1021/acs.joc.5b01872

  日期：2015.11.20

  A transition-metal-free, K2S2O8-mediated intra-molecular, oxidative nitrogenation/oxygenation of C(sp(3))-H in N-aryl benzylic amines followed by oxidation at the benzylic center has been developed for the synthesis of benzamidine/benzoxazine heterocycles, providing an expedient access to quinazolin-4(3H)-ones, N-aryl-2-arylbenzimidazoles, and 4H-3,1-benzoxazin-4-ones. A considerable amount of work dealing with the mechanistic study to understand the crucial intramolecular cyclization step largely favors an iminium ion as the key intermediate.