2-methylbenzene diazonium | 17333-74-3

• 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-methylbenzene diazonium
• 英文别名: o-Tolyldiazonium；o-Toluoldiazonium；2-Methylbenzoldiazonium；o-Toluol-diazoniumion；Toluol-diazonium-(2)；Toluol-2-diazonium；2-Methylbenzenediazonium
• CAS: 17333-74-3
• 化学式: C₇H₇N₂
• 分子量: 119.146
• InChiKey: NIPHBNBAJWTWQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methylbenzene diazonium 在 sodium hydroxide 、 trisodium arsenite 作用下， 生成 (2-甲基苯基)砷酸
  参考文献：
  名称：

  Karrer, Chemische Berichte, 1915, vol. 48, p. 310

  摘要：

  DOI：
• 作为产物：
  描述：

  邻甲苯胺 在 盐酸 、 sodium nitrite 、 氟硼酸钠 作用下， 以 水 为溶剂， 反应 1.17h， 生成 2-methylbenzene diazonium
  参考文献：
  名称：

  Identification of novel inhibitors of Aurora A with a 3-(pyrrolopyridin-2-yl)indazole scaffold

  摘要：

  A novel series of 3-(pyrrolopyridin-2-yl)indazole derivatives were synthesized and biologically evaluated for their anti-proliferative effects on five human cancer cell lines. As a result, all of them exhibited vigorous potency against HL60 cell line with IC50 values ranging from singe digital nanomolar to micromolar level. Besides, a majority of them displayed modest to good antiproliferative activities against the other four cell lines, including KB, SMMC-7721, HCT116, and A549. Particularly, compound 2y, as the most distinguished one in this series, demonstrated IC50 values of 8.3 nM and 1.3 nM against HL60 and HCT116 cell lines, respectively. Afterwards, for exploring the molecular target, compounds 2d, 2g and 2y were further selected to evaluate the inhibitory activities against a panel of kinases. Finally, they were identified to be targeting Aurora A kinase with significant selectivity over other kinases, such as CHK1, CDK2, MEK1, GSK3 beta, BRAF, IKK beta and PKC. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.02.004

文献信息

• Could Stress Cause Psychosis in Individuals Vulnerable to Schizophrenia?
  作者：Cheryl Corcoran、Lilianne Mujica-Parodi、Scott Yale、David Leitman、Dolores Malaspina

  DOI：10.1017/s1092852900022240

  日期：2002.1

  It has long been considered that psychosocial stress plays a role in the expression of symptoms in schizophrenia (SZ), as it interacts with latent neural vulnerability that stems from genetic liability and early environmental insult. Advances in the understanding of the neurobiology of the stress cascade in both animal and human studies lead to a plausible model by which this interaction may occur: through neurotoxic effects on the hippocampus that may involve synaptic remodeling. Of late, the neurodevelopmental model of SZ etiology has been favored. But an elaboration of this schema that credits the impact of postnatal events and considers a role for neurodegenerative changes may be more plausible, given the evidence for gene-environment interaction in SZ expression and progressive structural changes observed with magnetic resonance imaging. Furthermore, new insights into nongliotic neurotoxic effects such as apoptosis, failure of neurogenesis, and changes in circuitry lead to an expansion of the time frame in which environmental effects may mediate expression of SZ symptoms.

  摘要长期以来，人们一直认为社会心理压力在精神分裂症（SZ）的症状表现中起着一定的作用，因为它与源于遗传和早期环境伤害的潜在神经脆弱性相互作用。在动物和人体研究中，人们对压力级联神经生物学的认识取得了进展，从而为这种相互作用的发生提供了一个可信的模型：通过对海马的神经毒性作用，可能涉及突触重塑。近来，SZ 病因的神经发育模式一直受到青睐。但是，考虑到在 SZ 表达中基因与环境相互作用的证据以及磁共振成像观察到的渐进性结构变化，对这一模式进行阐述，将出生后事件的影响考虑在内，并考虑神经退行性变化的作用，可能更加合理。此外，对神经细胞凋亡、神经元生成失败和电路变化等非神经胶质细胞毒性效应的新认识，扩大了环境影响可能介导 SZ 症状表达的时间范围。
• The effect of <i>ortho</i> and <i>para</i> substituents on the formation of the <i>E</i> and <i>Z</i> isomers of the arylhydrazones obtained from diazonium coupling with methyl 3-aminocrotonate and 3-aminocrotononitrile
  作者：Jason V. Jollimore、Marc Vacheresse、Keith Vaughan、Donald L. Hooper

  DOI：10.1139/v96-029

  日期：1996.2.1

  Reaction of arene diazonium salts with 3-aminocrotononitrile or methyl 3-aminocrotonate affords the 2-aryl-hydrazono-3-oxobutanenitrile (1 or 3 and 3′) or the methyl 2-arylhydrazono-3-oxobutanoate (2 and 2′ or 4 and 4′). A series of these hydrazones has been prepared with a range of electron-withdrawing and -donating substituents in the ortho or para position of the aryl moiety. The hydrazones have been characterized by spectroscopic methods, with emphasis on the ¹H NMR spectra, which have been used to determine the configuration of the hydrazones as E or Z or a mixture of the two. The para-substituted hydrazononitriles (1) are formed as a single species, namely the Z isomer, whereas the ortho isomers are formed as a mixture of E and Z configurations (3 and 3′). The hydrazonobutanoates (2 and 2′ or 4 and 4′) are formed as E/Z mixtures regardless of the position of the substituent in the aryl moiety. Complete assignments of all signals in the ¹H NMR spectra have been made on the basis of the ability of the various substituents to participate in intramolecular hydrogen bonding and a mechanism is proposed to account for the variations in the proportions of E and Z isomers and the effect of the nature of the substituent on this ratio. ¹³C NMR spectra of selected hydrazones have been recorded as an aid to structure assignment. Key words: hydrazone, diazonium, NMR spectroscopy, E/Z isomers, crotonic acid derivatives.

  芳香族重氮盐与3-氨基丙烯腈或甲基3-氨基丙烯酸酯反应，得到2-芳基-叠氮基-3-氧代丁腈（1或3和3'）或甲基2-芳基叠氮基-3-氧代丁酸酯（2和2'或4和4'）。已制备了一系列这些叠氮基化合物，其中芳基部分的邻位或对位具有一系列电子吸引或供给取代基。这些叠氮基化合物已通过光谱方法进行表征，重点放在¹H NMR谱上，该谱已用于确定叠氮基的构型为E或Z或两者的混合物。对位取代的叠氮基腈（1）形成为单一种类，即Z异构体，而邻位异构体形成为E和Z构型的混合物（3和3'）。叠氮基丁酸酯（2和2'或4和4'）无论芳基部分的取代基位置如何，都形成为E/Z混合物。基于各种取代基参与分子内氢键形成的能力，已对¹H NMR谱中所有信号进行了完整的指认，并提出了一种机制来解释E和Z异构体的比例变化以及取代基性质对此比例的影响。已记录了选定叠氮基的¹³C NMR谱，以帮助结构指认。关键词：叠氮基，重氮盐，NMR光谱，E/Z异构体，丙烯酸衍生物。
• The synthesis of some substituted biphenyl-4-carboxylic acids, 4-biphenylylacetic acids, and 4-aminobiphenyls
  作者：D. J. Byron、G. W. Gray、R. C. Wilson

  DOI：10.1039/j39660000840

  日期：——

  The synthesis of a range of substituted biphenyl-4-carboxylic acids and 4-aminobiphenyls is described. Preparations are included for the parent biphenyl-4-carboxylic acid, and for 4-biphenylylacetic acid and three substituted 4-biphenylylacetic acids.

  描述了一系列取代的联苯-4-羧酸和4-氨基联苯的合成。包括母体联苯-4-羧酸，4-联苯基乙酸和三种取代的4-联苯基乙酸的制剂。
• Nano-Fe₃O₄ encapsulated-silica supported boron trifluoride as a novel heterogeneous solid acid for solvent-free synthesis of arylazo-1-naphthol derivatives
  作者：Abdolhamid Bamoniri、Naimeh Moshtael-Arani

  DOI：10.1039/c4ra12604a

  日期：——

  Fe₃O₄@SiO₂–BF₃ nanoparticles were prepared as a novel solid acid and effectively applied for the solvent-free synthesis of arylazo-1-naphthols at room temperature.

  Fe₃O₄@SiO₂-BF₃纳米颗粒被制备为一种新型固体酸，并有效地应用于室温下的无溶剂合成芳基偶氮基-1-萘酚。
• Anil-Synthese. 6. Mitteilung. Über die basenkatalysierte Umsetzung von methylsubstituierten 2<i>H</i>-Naphtho[1,2-<i>d</i>]triazol-2-yl-benzolen und -naphthalinen mit Anilen aromatischer Aldehyde
  作者：M. Brunold、A. E. Siegrist

  DOI：10.1002/hlca.19720550311

  日期：1972.4.20

  Methylgruppen in verschiedenen Stellungen des Benzolringes von 2H-Naphtho[1,2-d]triazol-2-yl-benzol können mit Anilen aromatischer Aldehyde in Dimethylformamid in Gegenwart von Kaliumhydroxid in Styrylgruppen übergeführt werden («Anil-Synthese»). Der Einfluss von Substituenten in Nachbarstellung zur Methylgruppe von 2-(p-Tolyl)-2H-naphtho[1, 2-d]triazol auf den Reaktionsablauf wird untersucht. Aus

  甲基丁二烯在苯丙酮丁醚中2 H-萘并[1,2- d ]三唑-2-基-苯甲酰苯胺中的丁苯胺在二甲基甲酰胺中的丁香中在二甲基甲酰胺中在丁香醚中氧化氢氧化钾，在施蒂尔格鲁皮彭·伯格恩施泰瑟·安登。在Nachbarstellung zur Methylgruppe von 2-（p -Tolyl）-2 H -naphtho [1，2- d ] triazol auf den Reaktionsablauf上的Der Einfluss von替代品。Gegenwart von Kaliumhydroxid 1,2,3-Triphenyl-7-（）中的二甲基甲酰胺中的Aus 2-Fluor-4-（2 H-萘[1，2- d ]-三唑-2-基）-甲苯和Anilen aromatischer Aldehyde entstehen在二甲基甲酰胺中2 H-萘[1，2- d]三唑-2-基）-1,4-二氢chinolin衍生物。