N-cyclopentyl-4-nitroaniline

• 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-cyclopentyl-4-nitroaniline
• 英文别名: N-cyclopentyl-4-nitrobenzenamine
• 化学式: C₁₁H₁₄N₂O₂
• mdl: MFCD01463611
• 分子量: 206.244
• InChiKey: CBVVMRGBJNMFOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.454
• 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：

  N-cyclopentyl-4-nitroaniline 在 5%-palladium/activated carbon 、 氢气 、 对甲苯磺酸 作用下， 以 乙醇 、 水 、 正丁醇 为溶剂， 反应 15.0h， 生成 5-cyclopentyl-7-((4-(cyclopentylamino)phenyl)amino)-[1,2,4]triazolo[4,3-f]pteridin-4(5H)-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel 7-amino-[1,2,4]triazolo[4,3-f]pteridinone, and 7-aminotetrazolo[1,5-f]pteridinone derivative as potent antitumor agents

  摘要：

  To develop novel therapeutic agents with anticancer activities, two series of novel 7-amino-[1,2,4]triazolo[4,3-f]pteridinone, and 7-aminotetrazolo[1,5-f]pteridinone derivatives were designed and synthesized. All compounds were tested for anti-proliferative activities against five cancer cell lines. The structure-activity relationships (SARs) studies were conducted through the variation in two regions, the moiety of A ring and the terminal aniline B on pteridinone core. 1-Methyl-1,2,4-triazole derivative L-7 with 2,6-dimethylpiperazine showed the most potent antiproliferative activity against A549, PC-3, HCT116, MCF-7 and MDA-MB-231 cell lines with IC50 values of 0.16 mu M, 0.30 mu M, 0.511 mu M, 0.30 mu M, and 0.70 mu M, respectively. Combined with the results of the molecular docking and enzymatic studies, the PLK1 was very likely to be one of the drug targets of compound L7. Furthermore, to clarify the anticancer mechanism of compound L7, further explorations in the bioactivity were conducted. The results showed that compound L7 obviously inhibited proliferation of A549 cell lines, induced a great decrease in mitochondrial membrane potential leading to apoptosis of cancer cells, suppressed the migration of tumor cells, and arrested G1 phase of A549 cells. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.12.009
• 作为产物：
  描述：

  对氟硝基苯 、 环戊胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以92%的产率得到N-cyclopentyl-4-nitroaniline
  参考文献：
  名称：

  Cu介导的苯胺衍生物选择性溴化及初步机理研究

  摘要：

  摘要 已开发出一种简单有效的苯胺、苯胺衍生物和类似物的溴化方法。给出了43个例子，最高产率为98%。包括取代苯胺、吡啶胺、N-取代苯胺、N,N-二取代苯胺、N-苯基-酰胺、N-苯基-磺酰胺和含氮杂环在内的不同底物都具有反应性并选择性地生成所需的溴代产物。该方法可用于合成药物中间体和喹喔啉衍生物。图形概要

  DOI：

  10.1080/00397911.2019.1598558

文献信息

• Cu-Al Hydrotalcite: An Efficient and Reusable Ligand-Free Catalyst for the Coupling of Aryl Chlorides with Aliphatic, Aromatic, and N(H)-Heterocyclic Amines
  作者：B. Sreedhar、R. Arundhathi、P. Reddy、M. Reddy、M. Kantam

  DOI：10.1055/s-0029-1216890

  日期：2009.8

  Copper-aluminum hydrotalcite catalysts were effectively used in the coupling of aryl chlorides with aliphatic, aromatic, and N(H)-heterocyclic amines to afford the corresponding N-alkylated/arylated amines in excellent yields. The catalyst was quantitatively recovered from the reaction by simple filtration and reused for a number of cycles with almost consistent activity.

  铜铝水滑石催化剂有效地用于将芳基氯与脂肪族、芳香族以及N(H)杂环胺偶联，从而以优异的产率得到相应的N-烷基化/芳基化胺。该催化剂通过简单的过滤从反应中定量回收，并可重复使用多个循环，其活性几乎保持一致。
• Copper-Mediated monochlorination of anilines and nitrogen-containing heterocycles
  作者：Xue-Yan Yang、Hong-Yi Zhao、Shuai Mao、San-Qi Zhang

  DOI：10.1080/00397911.2018.1518531

  日期：2018.10.18

  Abstract A simple and selective copper(II) chloride-mediated monochlorination of anilines and nitrogen-containing heterocycles has been developed. Stirring a mixture of aniline, copper(II) chloride, lithium chloride in EtOH under reflux condition produced 4-chloroaniline with high yield. Eighteen substrates including substituted anilines, N-substituted anilines, N,N-disubstituted anilines, 5-nitroindole and

  摘要 开发了一种简单且选择性的氯化铜 (II) 介导的苯胺和含氮杂环的单氯化反应。将苯胺、氯化铜(II)、氯化锂在乙醇中的混合物在回流条件下搅拌，以高产率制备4-氯苯胺。包括取代苯胺、N-取代苯胺、N,N-二取代苯胺、5-硝基吲哚和咔唑在内的 18 种底物均具有反应性，并以中等至优异的产率 (52%–98%) 提供所需产物。图形概要
• Cu(0)@Al₂O₃/SiO₂ NPs: an efficient reusable catalyst for the cross coupling reactions of aryl chlorides with amines and anilines
  作者：P. Linga Reddy、R. Arundhathi、Diwan S. Rawat

  DOI：10.1039/c5ra19337k

  日期：——

  of a wide range of alkyl/aryl amines including challenging anilines with aryl chlorides. The catalyst offers significant advantages such as brevity, milder reaction conditions, excellent yields and high functional group tolerance for C–N cross coupling when compared with the other reported methods. Moreover, this atom-economical methodology does not require an additional ligand or co-catalyst/activator

  研究了芳基氯化物与各种烷基/芳基胺的C–N交叉偶联反应，该反应由浸渍在氧化铝/二氧化硅载体（Cu（0）@Al 2 O 3 / SiO 2）上的铜纳米颗粒催化。使用XRD，XPS，HR-TEM，BET表面积，SEM-EDAX，H 2表征制备的催化剂的固有物理化学和结构性质-TPR和ICP-AES技术。该催化剂在各种烷基/芳基胺（包括挑战性苯胺）与芳基氯化物的交叉偶联中显示出极好的反应性和功效。与其他已报道的方法相比，该催化剂具有简便，反应条件温和，收率高和对C–N交联的官能团耐受性强等显着优势。而且，这种原子经济的方法不需要额外的配体或助催化剂/活化剂。该Cu（0）@Al 2 O 3 / SiO 2催化剂被有效地用于7-氯-4-（4-（2-（硝基苯苯基）哌嗪-1-基）喹诺酮的克级合成（2k）。通过连续使用五次来检查催化剂的坚固性。
• Two Component Recyclable Heterogeneous Catalyst, Process for Preparation Thereof and its Use for Preparation of Amines
  申请人：Likhar Pravin R.

  公开号：US20110313158A1

  公开（公告）日：2011-12-22

  The invention describes the development of highly efficient, recyclable two component system, CuAl-hydrotalcite/rac 1,1′-Binaphthalene-2,2′-diol catalytic system for the N-alkylation of electron deficient aryl chlorides in presence of potassium carbonate as a base at room temperature in 3-6 h, wherein the process is provided for the preparation of various secondary amines via C—N coupling reaction of aliphatic amines(aliphatic open chain, acyclic, benzyl amines and heterocyclic amines) with various aryl chlorides.

  该发明描述了开发高效、可回收的两组分体系，CuAl-水滑石/rac 1,1′-联萘-2,2′-二酚催化系统，用于在室温下在3-6小时内以碳酸钾为碱催化芳基氯化物的N-烷基化反应，其中该过程提供了通过脂肪胺（脂肪开链、无环、苄胺和杂环胺）与各种芳基氯化物进行C—N偶联反应制备各种二级胺的方法。
• Rapid Microwave-Assisted Reductive Amination of Ketones with Anilines
  作者：Barry Potter、Helen Bailey、Wesley Heaton、Nigel Vicker

  DOI：10.1055/s-2006-949639

  日期：2006.9

  Using microwave technology, a new protocol has been developed that improves the reaction rate and overall efficiency of the direct reductive amination of ketones with anilines. When using sodium triacetoxyborohydride as the reducing agent, high product yields and increased reaction rates are achieved for a variety of electronically different anilines. Furthermore, we have found that this protocol can

  使用微波技术，开发了一种新方案，可提高酮与苯胺直接还原胺化的反应速率和整体效率。当使用三乙酰氧基硼氢化钠作为还原剂时，各种电子不同的苯胺都可以实现高产率和更高的反应速率。此外，我们发现该协议也可以应用于醛类。