4-aminophenyl-1,3-benzenediamine | 65503-76-6

• 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: 4-aminophenyl-1,3-benzenediamine
• 英文别名: 3-(4-aminoanilino)aniline；(3-amino-phenyl)-(4-amino-phenyl)-amine；(3-Amino-phenyl)-(4-amino-phenyl)-amin；(3-aminophenyl)-(4-aminophenyl) amine；(3-aminophenyl)-(4-aminophenyl)-amine；3,4'-diaminodiphenylamine；3-N-(4-aminophenyl)benzene-1,3-diamine
• CAS: 65503-76-6
• 化学式: C₁₂H₁₃N₃
• 分子量: 199.255
• InChiKey: SAFZWWGZNZLALU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-aminophenyl-1,3-benzenediamine 在 盐酸 、 三乙胺 、 mercury dichloride 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 异丙醇 为溶剂， 反应 16.0h， 生成 N-(3-[4-[N’-(4-chloro-3-trifluoromethylphenyl)guanidino]phenylamino]phenyl) acetamide hydrochloride
  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：

  3-硝基氯苯 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 palladium on activated carbon 、 2-(二环己基膦基)联苯 作用下， 以 乙二醇二甲醚 、 乙醇 、 乙酸乙酯 为溶剂， 反应 48.25h， 生成 4-aminophenyl-1,3-benzenediamine
  参考文献：
  名称：

  用作金属光催化剂的多组分共价有机框架的可编程光催化活性

  摘要：

  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。

  DOI：

  10.1002/chem.202202967

文献信息

• NOVEL DIAMINE, POLYAMIC ACID, AND POLYIMIDE
  申请人：NISSAN CHEMICAL INDUSTRIES. LTD.

  公开号：US20160264520A1

  公开（公告）日：2016-09-15

  To provide a novel diamine, and a polyimide precursor and a polyimide using it. A diamine represented by the formula (1): wherein each of X 1 and X 5 which are independent of each other, is a single bond or the like; each of X 2 and X 4 which are independent of each other, is —CH 2 — or the like; X 3 is a C 1-6 alkylene or the like; each of Y 1 and Y 2 which are independent of each other, is a single bond or the like; R is a C 1-20 linear, branched or cyclic hydrocarbon group; and a is 0 or 1).

  提供一种新颖的二胺，以及使用它的聚酰亚胺前体和聚酰亚胺。一种由式（1）表示的二胺：其中X1和X5中的每一个独立的，是单键或类似物；X2和X4中的每一个独立的，是—CH2—或类似物；X3是C1-6烷基或类似物；Y1和Y2中的每一个独立的，是单键或类似物；R是C1-20线性、支链或环烃基；a为0或1。
• Novel hair coloring compositions for use in oxidative hair dyeing
  申请人：Lim Mu'lll

  公开号：US20050188480A1

  公开（公告）日：2005-09-01

  Hair dyeing compositions are provided which comprise at least one coupler selected from N-aryl-m-phenylenediamine derivatives, 2-substituted N-aryl-m-phenylenediamine derivatives, and N-aryl-m-diaminopyridine derivatives, in combination with and at least one diaminopyrazole primary intermediate.

  提供了包括至少一种偶联剂在内的染发配方，所选偶联剂包括N-芳基-m-苯二胺衍生物、2-取代N-芳基-m-苯二胺衍生物和N-芳基-m-二氨基吡啶衍生物，与至少一种二氨基吡唑原料中间体组合使用。
• 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。
• Anthraquinone compound and dyeing or printing method using the same
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0276686A2

  公开（公告）日：1988-08-03

  A compound of the following formula in the free acid form, wherein R and R, are each hydrogen or alkyl, A is a divalent group of the formula, or wherein R3, R4 and Rs are each-hydrogen, methyl, ethyl, methoxy or ethoxy, m is 0 or 1, n, u and v are each 0, 1 or 2, p is 0, 1, 2 or 3, q and s are each an integer of 2 to 6, and r is 1 or 2, B, is phenylene or naphthylene, Z, is vinyl, β-sulfatoethyl or the like, ℓ is 0, 1 or 2, and X is a group of the formula, or wherein R2 is hydrogen or alkyl, B2 is phenylene or naphthylene, Z2 is vinyl, β-sulfatoethyl or the like, R6 and R7 are each hydrogen, alkyl, phenyl, naphthyl or benzyl, and R, A an t are as defined above, which is useful for dyeing or printing fiber materials to give a dyed or printed product of a brilliant blue color superior in fastness properties such as light fastness and perspiration-light fastness, with superior build-up property.

  游离酸形式的下式化合物、 其中 R 和 R 分别是氢或烷基，A 是式中的二价基团、 或 其中 R3、R4 和 Rs 各为氢、甲基、乙基、甲氧基或乙氧基，m 为 0 或 1，n、u 和 v 各为 0、1 或 2，p 为 0、1、2 或 3，q 和 s 各为 2 至 6 的整数，r 为 1 或 2，B 为亚苯基或萘基，Z 为乙烯基、β-硫代乙基或类似物，ℓ 为 0、1 或 2，X 为式中的基团、 或 其中 R2 是氢或烷基，B2 是亚苯基或萘基，Z2 是乙烯基、β-萘磺酸乙基或类似物，R6 和 R7 分别是氢、烷基、苯基、萘基或苄基，R、A 和 t 如上文所定义，可用于纤维材料的染色或印花，使染色或印花产品呈现艳丽的蓝色，具有优异的耐光牢度和耐汗耐光牢度等牢度特性，并具有优异的堆积特性。