3-硝基-N-(4-硝基苯基)苯胺 | 15979-87-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-硝基-N-(4-硝基苯基)苯胺
• 英文名称: 3-nitro-N-(4-nitrophenyl)aniline
• 英文别名: 4,3'-dinitrodiphenylamine；(3-nitro-phenyl)-(4-nitro-phenyl)-amine；(3-Nitro-phenyl)-(4-nitro-phenyl)-amin；3.4'-Dinitro-diphenylamin；3-nitro-N-(4-nitrophenyl)-benzenamine；3,4'-Dinitro-diphenylamin；3-Nitro-N-(4-nitrophenyl)benzenamine
• CAS: 15979-87-0
• 化学式: C₁₂H₉N₃O₄
• 分子量: 259.221
• InChiKey: GBRRZYZALUGPSM-UHFFFAOYSA-N

物化性质

• 熔点：
  217 °C
• 沸点：
  440.1±30.0 °C(Predicted)
• 密度：
  1.446±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-硝基-N-(4-硝基苯基)苯胺 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 、 mercury dichloride 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 55.0 ℃ 、303.99 kPa 条件下， 反应 16.0h， 生成 3-[4'-(phenylguanidino)phenylamino]phenylguanidine dihydrochloride
  参考文献：
  名称：

  Guanidinium-based derivatives: Searching for new kinase inhibitors

  摘要：

  Considering the structural similarities between the kinase inhibitor sorafenib and 4,4'-bis-guanidinium derivatives previously prepared by Rozas and co., which display interesting cytotoxicity in cancer cells, we have studied whether this activity could result from kinase inhibition. Five new families have been prepared consisting of unsubstituted and aryl-substituted 3,4'-bis-guanidiniums, 3,4'-bis-2-aminoimidazolinium and 3-acetamide-4'-(4-chloro-3-trifluoromethylphenyl)guanidinium derivatives. Cytotoxicity (measuring the IC50 values) and apoptosis studies in human HL-60 promyelocytic leukemia cells were carried out for these compounds. Additionally, their potential inhibitory effect was explored on a panel of kinases known to be involved in apoptotic pathways. The previously prepared cytotoxic 4,4'-bis-guanidiniums did not inhibit any of these kinases; however, some of the novel 3,4'-substituted derivatives showed a high percentage inhibition of RAF-1/MEK-1, for which the potential mode of binding was evaluated by docking studies. The interesting antitumour properties showed by these compounds open up new exciting lines of investigation for kinase inhibitors as anticancer agents and also highlights the relevance of the guanidinium moiety for protein kinase inhibitors chemical design. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.025
• 作为产物：
  描述：

  N-(4-nitro-benzenesulfonyl)-N'-(3-nitro-phenyl)-guanidine 在 sodium hydroxide 作用下， 生成 3-硝基-N-(4-硝基苯基)苯胺
  参考文献：
  名称：

  Backer; Wadman, Recueil des Travaux Chimiques des Pays-Bas, 1949, vol. 68, p. 595,602

  摘要：

  DOI：

文献信息

• Iron/Copper-Cocatalyzed Ullmann N,O-Arylation Using FeCl₃, CuO, and <i>rac</i>-1,1′-Binaphthyl-2,2′-diol
  作者：Hua Fu、Zhe Wang、Yuyang Jiang、Yufen Zhao

  DOI：10.1055/s-2008-1078214

  日期：——

  We have developed an efficient and inexpensive bimetallic catalyst FeCl3, CuO, and rac-BINOL that could promote N,O-arylation of aliphatic, arylamines, and phenols. The cross-coupling reaction conditions have high tolerance of various functional groups. This versatile and efficient iron/copper-cocatalyst can widely be used in the synthesis of the compounds containing ­(aryl)C-N or (aryl)C-O(aryl) bond.

  我们开发了一种高效且廉价的双金属催化剂FeCl3、CuO和rac-BINOL，可促进脂肪族、芳香胺和酚的N,O-芳基化反应。该交叉偶联反应条件对各种功能团具有良好的耐受性。这种多功能且高效的铁/铜协同催化剂可以广泛应用于含有(芳基)C-N或(芳基)C-O(芳基)键的化合物合成中。
• High-Pressure Synthesis of Oligoanilines
  作者：David J. Young、Christopher L. Brown、I. Wayan Muderawan

  DOI：10.1055/s-2003-42434

  日期：——

  Aniline oligomers can be prepared cleanly and in high yield by the high-pressure promoted SNAr reaction of aromatic amines with fluoronitrobenzenes followed by reduction of the nitro group.

  通过高压促进芳香胺与氟硝基苯的 SNAr 反应，然后还原硝基，可以清洁、高产地制备苯胺低聚物。
• A structural study of N,N′-bis-aryl-N′′-acylguanidines
  作者：Daniel H. O'Donovan、Brendan Kelly、Elena Diez-Cecilia、Martin Kitson、Isabel Rozas

  DOI：10.1039/c3nj00285c

  日期：——

  characterisation of these derivatives. Hence, the present study examines isomerism in N,N′-bis-aryl-N′′-acylguanidines using low temperature NMR spectroscopy in tandem with Density Functional Theory (DFT), Natural Bond Analysis (NBO) and the Gauge-Invariant Atomic Orbital (GIAO) approach for calculating the NMR chemical shifts associated with each isomer. It was found that the structural preference of these compounds

  的Ñ -芳基-和Ñ -acylguanidine结构基序是用于分子的一些重要类别，包括医药，催化剂和天然产品的功能是必不可少的。归因于胍亚基内的互变异构，关于胍双键的E / Z异构和构象异构，结合了两个基序的化合物可以作为不同的异构体存在。这种复杂的现象导致无法解析的宽信号NMR光谱，使这些衍生物的表征变得非常复杂。因此，本研究探讨了N，N'-双-芳基-N中的异构现象结合密度泛函理论（DFT），自然键分析（NBO）和量规不变原子轨道（GIAO）方法使用低温NMR光谱法来计算′'-酰基胍，以计算与每个异构体相关的NMR化学位移。已经发现，这些化合物的结构偏好受到分子内氢键（IMHB）作用的强烈影响。
• Acridine‐Functionalized Covalent Organic Frameworks (COFs) as Photocatalysts for Metallaphotocatalytic C−N Cross‐Coupling
  作者：Michael Traxler、Sebastian Gisbertz、Pradip Pachfule、Johannes Schmidt、Jérôme Roeser、Susanne Reischauer、Jabor Rabeah、Bartholomäus Pieber、Arne Thomas

  DOI：10.1002/anie.202117738

  日期：2022.5.16

  A new family of porous crystalline COFs bearing acridine moieties was synthesized and applied as photocatalysts in metallaphotocatalytic C−N cross-coupling. Among these materials the fully β-ketoenamine-linked COF showed the highest catalytic activity and was shown to be recyclable and even catalyzed the cross-coupling efficiently under green light irradiation.

  合成了一个新的带有吖啶部分的多孔晶体COF家族，并将其用作金属光催化CN交叉偶联中的光催化剂。在这些材料中，完全β-酮烯胺连接的COF表现出最高的催化活性，并且可回收，甚至在绿光照射下有效催化交叉偶联。
• Programmable Photocatalytic Activity of Multicomponent Covalent Organic Frameworks Used as Metallaphotocatalysts
  作者：Michael Traxler、Susanne Reischauer、Sarah Vogl、Jérôme Roeser、Jabor Rabeah、Christopher Penschke、Peter Saalfrank、Bartholomäus Pieber、Arne Thomas

  DOI：10.1002/chem.202202967

  日期：2023.1.18

  Various multicomponent COFs bearing both a moiety for photosensitization and complexation of nickel catalysts were synthesized using reticulation with different 1,3,5-triformylbenzene nodes. This enabled the switching between persistent, charge-separated species or efficient charge-carrier mobility for different metallaphotocatalytic cross-coupling reactions based on the node unit. The frameworks showed

  使用具有不同 1,3,5-三甲酰苯节点的网状结构合成了多种多组分 COF，这些 COF 具有光敏化部分和镍催化剂的络合部分。这使得基于节点单元的不同金属光催化交叉偶联反应能够在持久的、电荷分离的物种或有效的电荷载流子迁移率之间切换。这些框架显示出可回收性和使用红光照射驱动反应的可能性。