2-methoxy-N,N-dimethyl-4-nitroaniline | 90437-76-6

• 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: 2-methoxy-N,N-dimethyl-4-nitroaniline
• CAS: 90437-76-6
• 化学式: C₉H₁₂N₂O₃
• 分子量: 196.206
• InChiKey: YDODYNVOKLHYNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methoxy-N,N-dimethyl-4-nitroaniline 在 硝酸 作用下， 生成 2-methoxy-N-methyl-4,6,N-trinitro-aniline
  参考文献：
  名称：

  Catecholamines and their metabolites in the brain and urine of rats with experimental Parkinson’s disease

  摘要：

  The content of catecholamines and their metabolites in the brain and the relationship between cerebral catecholamine levels and their urinary excretion were studied in rats with 6-OHDA-induced hemiparkinsonism. 6-OHDA reduced brain concentrations of dopamine, DOPAC, and homovanilic acid and urinary excretion of dopamine, dioxyphenilalanine, and DOPAC by more than 90%. A positive correlation was found between the concentrations of these metabolites in the urine and striatum. Measurement of urinary catecholamines and their metabolites is a perspective test for evaluating the status of the dopaminergic nigrosostriate system of the brain in experimental parkinsonism.

  DOI：

  10.1007/bf02766101
• 作为产物：
  描述：

  2-甲基金刚烷 在 硫酸 、 水 、 sodium nitrite 作用下， 生成 2-methoxy-N,N-dimethyl-4-nitroaniline
  参考文献：
  名称：

  Catecholamines and their metabolites in the brain and urine of rats with experimental Parkinson’s disease

  摘要：

  The content of catecholamines and their metabolites in the brain and the relationship between cerebral catecholamine levels and their urinary excretion were studied in rats with 6-OHDA-induced hemiparkinsonism. 6-OHDA reduced brain concentrations of dopamine, DOPAC, and homovanilic acid and urinary excretion of dopamine, dioxyphenilalanine, and DOPAC by more than 90%. A positive correlation was found between the concentrations of these metabolites in the urine and striatum. Measurement of urinary catecholamines and their metabolites is a perspective test for evaluating the status of the dopaminergic nigrosostriate system of the brain in experimental parkinsonism.

  DOI：

  10.1007/bf02766101

文献信息

• Nitrophenyl ethers as possible photoaffinity labels. The nucleophilic aromatic photosubstitution revisited.
  作者：J. Cerveló、M. Figueredo、J. Marquet、M. Moreno-Manas、J. Bertrán、J.M. Lluch

  DOI：10.1016/s0040-4039(01)90206-0

  日期：1984.1

  The photoreactions of nitrophenyl ethers with simple primary and secondary amines show a remarkable nucleophile influence on the reaction orientation. Calculations indicate a change from charge controlled to frontier orbital controlled reactions moving from smaller to larger amines.

  硝基苯醚与简单的伯胺和仲胺的光反应显示出显着的亲核试剂对反应取向的影响。计算表明从电荷控制到边界轨道控制的反应从较小的胺到较大的胺的变化。
• Isoindol-1,3-dione and isoindol-1-one derivatives with high binding affinity to β-amyloid fibrils
  作者：Hyu Ji Lee、Soo Jeong Lim、Seung Jun Oh、Dae Hyuk Moon、Dong Jin Kim、Jinsung Tae、Kyung Ho Yoo

  DOI：10.1016/j.bmcl.2008.01.066

  日期：2008.3

  These 23 compounds were evaluated by competitive binding assay against aggregated Abeta42 fibrils using [(125)I]TZDM. All the isoindolone derivatives showed very good binding affinities with K(i) values in the subnanomolar range (0.42-0.94 nM). Among them, isoindol-1,3-diones 1i and 1k and isoindol-1-ones 2c and 2i exhibited excellent binding affinities (K(i)=0.42-0.44 and 0.46-0.49 nM) than those of

  基于吲哚洛芬和PIB的结构特征，设计并合成了一系列的isoindol-1,3-diones 1a-k和isoindol-1-ones 2a-1。使用[（125）I] TZDM，通过竞争性结合结合聚集Abeta42原纤维的竞争性测定法评估了这23种化合物。所有的异吲哚酮衍生物均表现出非常好的结合亲和力，其K（i）值在亚纳摩尔范围（0.42-0.94 nM）内。其中，isoindol-1,3-diones 1i和1k以及isoindol-1-ones 2c和2i与Indoprofen（K（i））相比具有极好的结合亲和力（K（i）= 0.42-0.44和0.46-0.49 nM）。 ＝ 0.52nM）和PIB（K（i）＝ 0.70nM）。这些结果表明，异吲哚酮可用作潜在的AD诊断探针的支架，以监测Abeta纤维。
• 1-Benzyl-3-aryl-2-thiohydantoin Derivatives as New Anti-<i>Trypanosoma brucei</i> Agents: SAR and in Vivo Efficacy
  作者：Andriy Buchynskyy、J. Robert Gillespie、Zackary M. Herbst、Ranae M. Ranade、Frederick S. Buckner、Michael H. Gelb

  DOI：10.1021/acsmedchemlett.7b00230

  日期：2017.8.10

  high throughput screening and subsequent hit validation identified compound 1 as an inhibitor of Trypanosoma brucei parasite growth. Extensive structure–activity relationship optimization based on antiparasitic activity led to the highly potent compounds, 1-(4-fluorobenzyl)-3-(4-dimethylamino-3-chlorophenyl)-2-thiohydantoin (68) and 1-(2-chloro-4-fluorobenzyl)-3-(4-dimethylamino-3-methoxyphenyl)-2-thiohydantoin

  高通量筛选和随后的命中验证确定化合物1为布鲁氏锥虫寄生虫生长的抑制剂。基于抗寄生虫活性的广泛的结构-活性关系优化导致了高效化合物1-（4-氟苄基）-3-（4-二甲基氨基-3-氯苯基）-2-硫代乙内酰脲（68）和1-（2-氯-4-氟苄基）-3-（4-二甲基氨基-3-甲氧基苯基）-2-硫代乙内酰脲（76），布氏锥虫EC 50分别为3和2 nM。与化合物1相比，这表示效力提高了100倍以上。68和76的体内功效实验 在人类非洲锥虫病的急性小鼠模型中，口服治疗每天4次，每天两次，剂量为50 mg / kg，治愈率为100％。
• A Combined Experimental and Theoretical Approach toward the Development of Optimized Luminescent Carbostyrils
  作者：Gernot A. Strohmeier、Walter M. F. Fabian、Georg Uray

  DOI：10.1002/hlca.200490009

  日期：2004.1

  The synthesis and photophysical data of new carbostyrils (quinoline-2(1H)-ones) with the longest hitherto observed absorption- and emission wavelengths are described. Introduction of 6-amino, 7-MeO, and 4-(CF3) substituents enabled us to rise the absorption and fluorescence maxima up to 414 and 557 nm, respectively. Supported by semi-empirical and ab initio calculations, the 6,7-(1,4-diazine)-fused

  描述了迄今观察到的最长的吸收和发射波长的新咔唑（喹啉-2（1 H）-ones）的合成和光物理数据。引入6-氨基，7-MeO和4-（CF 3）取代基使我们能够将吸收和荧光最大值分别提高到414和557 nm。在半经验和从头算计算的支持下，6,7-（1,4-二嗪）融合的羧甲基苯乙烯23b在最大440 nm处显示最大吸收，量子产率高达0.9，并且斯托克斯位移大（> 100 nm） ），可与已知的最佳香豆素生色团相比。新的荧光团在pH值6到10之间都不是pH敏感的，也不易受O 2的影响。淬火。在pH 3时，发出的光呈绿白色，这是由于质子化的三个不同阶段引起的。
• Aryne‐Enabled C−N Arylation of Anilines
  作者：Thomas Sephton、Anastasios Charitou、Cristina Trujillo、Jonathan M. Large、Sam Butterworth、Michael F. Greaney

  DOI：10.1002/anie.202310583

  日期：2023.12.4

  A transition metal-free C−N arylation of easily accessible tertiary anilines enabled by bifunctional arynes is described. The reaction proceeds via a tandem nucleophilic attack of anilines to arynes, followed by a Smiles-Truce rearrangement to furnish synthetically valuable and densely substituted biaryls. This protocol was further utilized for heterocyclic scaffolds, providing access to medium size

  描述了由双官能团芳烃实现的易于接近的叔苯胺的无过渡金属 C-N 芳基化。反应通过苯胺转化为芳烃的串联亲核攻击进行，然后进行 Smiles-Truce 重排以提供具有合成价值且密集取代的联芳基。该方案进一步用于杂环支架，通过 n+2 碳插入提供中等大小的氮杂杂环。