N-benzyl-2-bromo-4-methoxybenzeneamine | 162712-04-1

• 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-methoxybenzeneamine
• 英文别名: benzyl-(2-bromo-4-methoxyphenyl)amine；N-benzyl-2-bromo-4-methoxyaniline
• CAS: 162712-04-1
• 化学式: C₁₄H₁₄BrNO
• 分子量: 292.175
• InChiKey: DJNPRKTUIWEVJW-UHFFFAOYSA-N

物化性质

• 沸点：
  385.1±37.0 °C(Predicted)
• 密度：
  1.392±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  21.3
• 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-methoxybenzeneamine 在 四(三苯基膦)钯 sodium carbonate 、 苯基锂 作用下， 以 乙二醇二甲醚 、 二丁醚 、 水 为溶剂， 反应 24.75h， 生成 (+)-1-benzyl-5-methoxy-3-(1-methylpentyl)-1H-indole
  参考文献：
  名称：

  Enantioselective Carbolithiation Initiated Cascade Reactions

  摘要：

  Enantioselective cascade reactions are very powerful synthetic protocols for the assembly of complex architectures. Our current approach is to exploit a (-)-sparteine-controlled enantioselective carbolithiation of 2-propenylarylamines to provide chiral intermediates, which depending upon choice of electrophile are subsequently in situ converted into products of increasing complexity. The chiral center, formed in high enantiomeric ratio in the first carbolithiation step, is carried through the cascade reaction sequence to the final products and is independent of electrophile used. The scope of the cascade reaction is outlined in terms of reaction conditions, alkyllithiums, and electrophiles.

  DOI：

  10.1021/ja060076g
• 作为产物：
  描述：

  N-苄基-4-甲氧基苯胺 在 溴 、 溶剂黄146 作用下， 反应 2.0h， 以90%的产率得到N-benzyl-2-bromo-4-methoxybenzeneamine
  参考文献：
  名称：

  1,3-二氢-3,3-二甲基-2 H-吲哚-2-酮衍生物的合成可能是非甾体类强心药

  摘要：

  合成了新的取代的1,3-二氢-3,3-二甲基-2 H-吲哚-2-酮衍生物19-29和34-43，并检查了它们在离体狗心室组织中的肌力活性。其中，化合物26（2-（2,3-二甲氧基苄氨基）-N-（3,3,7-三甲基-2-氧代-2,3-二氢-1 H-吲哚-5-基）乙酰胺）显示有力的活动。

  DOI：

  10.1002/jhet.5570320101

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，
• An Unprecedented Pd-Catalyzed Carbonylative Route to Fused Furo[3,4-<i>b</i>]indol-1-ones
  作者：Alessandra Acerbi、Carla Carfagna、Mirco Costa、Raffaella Mancuso、Bartolo Gabriele、Nicola Della Ca'

  DOI：10.1002/chem.201706067

  日期：2018.4.3

  A novel and efficient catalytic approach to functionalized furo[3,4‐b]indol‐1‐ones is reported. It is based on a palladium‐catalyzed sequential process involving an initial cyclization of 2‐(hydroxypropyn‐1‐yl)anilines to form the indole moiety, followed by insertion of carbon monoxide and a second annulation step to build a lactone ring. In a single transformation, two fused heterocycles and three

  报道了一种新颖且有效的催化方法，用于官能化的呋喃[3,4- b ]吲哚-1-酮。它基于钯催化的顺序过程，该过程包括2-（羟基丙炔-1-基）苯胺的初始环化以形成吲哚部分，然后插入一氧化碳和第二步环合步骤以建立内酯环。在一次转换中，生成两个稠合杂环和三个新键（CN，CC和OC）。本方法论可从容易获得的试剂开始直接进入结构复杂的分子。
• Suzuki cross-coupling mediated by tetradentate N-heterocyclic carbene (NHC)–palladium complexes in an environmentally benign solvent
  作者：Yuanhong Zhao、Yongyun Zhou、Dandan Ma、Jingping Liu、Liang Li、Tony Y. Zhang、Hongbin Zhang

  DOI：10.1039/b302646a

  日期：——

  A highly effective, easy to handle and environmentally benign process for palladium mediated Suzuki cross-coupling was developed. By utilizing a solid support based NHC–palladium catalyst, cross couplings of aryl bromides with phenylboronic acid were achieved in neat water under air. A high ratio of substrate to catalyst was also realized.

  开发了一种高效、易操作且对环境友好的钯介导Suzuki交叉偶联反应工艺。通过利用基于固体支持的NHC–钯催化剂，将芳基溴化物与苯硼酸在空气中的纯水中进行了交叉偶联。同时实现了高的底物与催化剂的比例。
• The novel compound MP407 inhibits platelet aggregation through cyclic AMP-dependent processes
  作者：Chung-Shuen Lin、Tso-Hsiao Chen、I-Hsin Lin、An-Rong Lee、Tz-Chong Chou

  DOI：10.1016/j.ejphar.2017.09.024

  日期：2017.11

  investigated the effects of the new synthesized compound, MP407 on platelet aggregation and further elucidated the underlying mechanisms. Our results demonstrated that MP407 dose-dependently inhibited collagen-induced platelet aggregation, thromboxane B2 (TXB2) production, intracellular Ca2+ mobilization, platelet membrane GPIIb/IIIa expression, and the phosphorylation of Akt, GSK3β, p38MAPK, and phospho

  血小板过度活跃对于引发多种血管疾病（如动脉粥样硬化）起着至关重要的作用。因此，开发有效的抗血小板剂对于改善血小板相关疾病是必要的。在这项研究中，我们调查了新合成的化合物MP407对血小板聚集的影响，并进一步阐明了其潜在机制。我们的结果表明MP407剂量依赖性地抑制胶原蛋白诱导的血小板聚集，血栓烷B2（TXB2）产生，细胞内Ca2 +动员，血小板膜GPIIb / IIIa表达以及Akt，GSK3β，p38MAPK和磷酸（Ser）PKC底物的磷酸化（第47页）。此外，MP407能够增加静止和活化血小板中环状AMP的形成。但是，用2'5'-ddAdo阻止循环AMP的形成，腺苷酸环化酶的抑制剂，极大地逆转了MP407的抗血小板活性和相关的血小板活化途径。MP407还增强了胶原蛋白刺激的血小板中Ser157处的VASP磷酸化作用，该作用被添加2'5'-ddAdo减弱。因此，MP407的抗血小板活性可
• 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.