5-nitro-N-benzylidene-1,2-phenylenediamine | 167558-65-8

• 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: 5-nitro-N-benzylidene-1,2-phenylenediamine
• 英文别名: 4-Nitro-N2-(phenylmethylene)-1,2-benzenediamine；2-(benzylideneamino)-4-nitroaniline
• CAS: 167558-65-8
• 化学式: C₁₃H₁₁N₃O₂
• 分子量: 241.249
• InChiKey: CLJKVTWAVBVYEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 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：
  84.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-nitro-N-benzylidene-1,2-phenylenediamine 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 N¹-benzyl-5-nitrobenzene-1,2-diamine
  参考文献：
  名称：

  Selectivity control during the solid supported protic acids catalysed synthesis of 1,2-disubstituted benzimidazoles and mechanistic insight to rationalize selectivity

  摘要：

  在形成1,2-二取代苯并咪唑的反应中，已经实现了选择性控制，该反应是对邻苯二胺与醛类在固态酸催化剂的存在下进行的，同时选择了合适的反应介质。研究发现，吸附在硅胶上的高氯酸（HClO4–SiO2）是合成1,2-二取代苯并咪唑在室温下使用乙醇的最有效催化体系。除了催化剂和溶剂之外，醛的电子和空间因素以及邻苯二胺的电子因素也是决定选择性的显著因素。对于1,2-二取代苯并咪唑的形成机制的理解也已被概述，这将有助于解释在设定实验参数下选择性控制的来源。

  DOI：

  10.1039/c2ra21994h
• 作为产物：
  描述：

  苯甲醛 、 4-硝基邻苯二胺 在 perchloric acid on silica gel 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 5-nitro-N-benzylidene-1,2-phenylenediamine
  参考文献：
  名称：

  Selectivity control during the solid supported protic acids catalysed synthesis of 1,2-disubstituted benzimidazoles and mechanistic insight to rationalize selectivity

  摘要：

  在形成1,2-二取代苯并咪唑的反应中，已经实现了选择性控制，该反应是对邻苯二胺与醛类在固态酸催化剂的存在下进行的，同时选择了合适的反应介质。研究发现，吸附在硅胶上的高氯酸（HClO4–SiO2）是合成1,2-二取代苯并咪唑在室温下使用乙醇的最有效催化体系。除了催化剂和溶剂之外，醛的电子和空间因素以及邻苯二胺的电子因素也是决定选择性的显著因素。对于1,2-二取代苯并咪唑的形成机制的理解也已被概述，这将有助于解释在设定实验参数下选择性控制的来源。

  DOI：

  10.1039/c2ra21994h

文献信息

• Reduced Schiff-base assisted novel dihydrogenphosphate–water polymer
  作者：Sasanka Dalapati、Md. Akhtarul Alam、Sankar Jana、Nikhil Guchhait

  DOI：10.1039/c2ce25502b

  日期：——

  Reduced Schiff bases with a common p-nitro-o-phenylenediamine moiety have been synthesised and their structures have been characterized by single-crystal structural analysis. Schiff bases having self-complementary H-bond donors and H-bond acceptors can form a “scissors” like structure through intermolecular H-bonding interaction. Reduced Schiff bases interact with biologically important dihydrogenphosphate ion and form stable complexes. Furthermore, dihydrogenphosphate and water form an unprecedented self-assembled dihydrogenphosphate–water [H2PO4·H2O]nn− 1D supramolecular polymer upon complexation with reduced Schiff bases.

  合成了具有共通p-硝基-o-苯二胺基团的还原施夫碱，并通过单晶结构分析对其结构进行了表征。具有自互补氢键供体和氢键受体的施夫碱可以通过分子间氢键相互作用形成“剪刀”状结构。还原施夫碱与生物学上重要的二氢磷酸根离子相互作用，形成稳定的复合物。此外，二氢磷酸根和水在与还原施夫碱络合时形成前所未见的自组装二氢磷酸根-水 [H2PO4·H2O]nn⁻ 1D 超分子聚合物。
• 一种邻苯二胺席夫碱衍生物及其制备方法与 应用
  申请人：重庆理工大学

  公开号：CN106496065B

  公开（公告）日：2018-10-23

  本发明公开了一种邻苯二胺席夫碱衍生物及其制备方法与应用，其结构式如下：制备时，先在水热反应釜中，加入一定体积的水以及适量的4‑硝基邻苯二胺和苯甲醛，然后在100℃‑150℃下进行反应10‑90分钟；反应结束后，将反应釜冷却到室温后，对反应产物进行过滤、干燥、重结晶和干燥，即可得到邻苯二胺席夫碱衍生物。本制备方法无毒无害，且不使用任何催化剂，主要利用高温水的高扩散系数和强溶解性，从而使反应高效、简便地进行。本发明邻苯二胺席夫碱衍生物化学稳定性好，溶解性好，且具有荧光性质。
• Reusable Amine-Based Structural Motifs for Green House Gas (CO₂) Fixation
  作者：Sasanka Dalapati、Sankar Jana、Rajat Saha、Md. Akhtarul Alam、Nikhil Guchhait

  DOI：10.1021/ol301241k

  日期：2012.7.6

  A series of compounds with an amine based structural motif (ASM) have been synthesized for efficient atmospheric CO2 fixation. The H-bonded ASM bicarbonate complexes were formed with an in situ generated HCO3- ion. The complexes have been characterized by IR, C-13 NMR, and X-ray single-crystal structural analysis. ASM bicarbonate salts have been converted to pure ASMs in quantitative yield under mild conditions for recycling processes.
• Selectivity control during the solid supported protic acids catalysed synthesis of 1,2-disubstituted benzimidazoles and mechanistic insight to rationalize selectivity
  作者：Dinesh Kumar、Damodara N. Kommi、Rajesh Chebolu、Sanjeev K. Garg、Raj Kumar、Asit K. Chakraborti

  DOI：10.1039/c2ra21994h

  日期：——

  Selectivity control during the formation of 1,2-disubstituted benzimidazoles has been achieved for the reaction of o-phenylenediamine with aldehydes in the presence of solid supported protic acids as catalysts and choosing an appropriate reaction medium. Perchloric acid adsorbed on silica-gel (HClO4–SiO2) was found to be the most effective catalyst system for the synthesis of 1,2-disubstituted benzimidazoles in EtOH at rt. Apart from the catalyst and solvent, the electronic and steric factors of the aldehyde and the electronic factor of the o-phenylenediamine are also significant contributory factors in dictating the selectivity. An understanding of the mechanistic course of the formation of the 1,2-disubstituted benzimidazoles has been outlined that would rationalise the origin of selectivity control under the set experimental parameters.

  在形成1,2-二取代苯并咪唑的反应中，已经实现了选择性控制，该反应是对邻苯二胺与醛类在固态酸催化剂的存在下进行的，同时选择了合适的反应介质。研究发现，吸附在硅胶上的高氯酸（HClO4–SiO2）是合成1,2-二取代苯并咪唑在室温下使用乙醇的最有效催化体系。除了催化剂和溶剂之外，醛的电子和空间因素以及邻苯二胺的电子因素也是决定选择性的显著因素。对于1,2-二取代苯并咪唑的形成机制的理解也已被概述，这将有助于解释在设定实验参数下选择性控制的来源。
• Design, synthesis, and enzyme kinetics of novel benzimidazole and quinoxaline derivatives as methionine synthase inhibitors
  作者：Hosam Elshihawy、Mohamed A. Helal、Mohamed Said、Mohamed A. Hammad

  DOI：10.1016/j.bmc.2013.10.052

  日期：2014.1

  Methionine synthase catalyzes the transfer of a methyl group from 5-methyltetrahydrofolate to homocysteine, producing methionine and tetrahydrofolate. Benzimidazole and deazatetrahydrofolates derivatives have been shown to inhibit methionine synthase by competing with the substrate 5-methyltetrahydrofolate. In this study, a novel series of substituted benzimidazoles and quinoxalines were designed and assessed for inhibitory activity against purified rat liver methionine synthase using a radiometric enzyme assay. Compounds 3g, 3j, and 5c showed the highest activity against methionine synthase (IC50: 20 mu M, 18 mu M, 9 mu M, respectively). Kinetic analysis of these compounds using Lineweaver-Burk plots revealed characteristics of mixed inhibition for 3g and 5c; and uncompetitive inhibition for 3j. Docking study into a homology model of the rat methionine synthase gave insights into the molecular determinants of the activity of this class of compounds. The identification of these drug-like inhibitors could lead the design of the next generation modulators of methionine synthase. (C) 2013 Elsevier Ltd. All rights reserved.