N-(2-硝基苯亚甲基)对甲苯胺 | 17064-82-3

• 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: N-(2-硝基苯亚甲基)对甲苯胺
• 英文名称: N-(2-nitrobenzylidene)-p-toluidine
• 英文别名: 4-methyl-(2-nitrobenzylidene)aniline；N-(o-Nitrobenzyliden)-p'-methylanilin；o-Nitrobenzaldehyd-p-tolylimin；N-<2-Nitro-benzyliden>-p-toluidin；N-(2-Nitro-benzyliden)-p-toluidin；2-Nitro-benzaldehyd-p-tolylimin；4-methyl-N-(2-nitrobenzylidene)aniline；(2-Nitro-benzaldehyd)-p-tolylimid；(2-Nitro-benzal)-p-toluidin；N-(P-tolyl)-o-nitrobenzaldimine；N-(4-methylphenyl)-1-(2-nitrophenyl)methanimine
• CAS: 17064-82-3
• 化学式: C₁₄H₁₂N₂O₂
• 分子量: 240.261
• InChiKey: YKRSQWCMPJDBOD-UHFFFAOYSA-N

物化性质

• 熔点：
  75 °C
• 沸点：
  55 °C(Press: 0.1 Torr)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-硝基苯亚甲基)对甲苯胺 在 sodium sulfide 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 24.17h， 生成 ethyl 2-phenylquinoline-3-carboxylate
  参考文献：
  名称：

  Preparation of axially chiral quinolinium salts related to NAD+ models: new investigations of these biomimetic models as ‘chiral amide-transferring agents’

  摘要：

  The general purpose of this work is to investigate the potential of biomimetic NAD(+) models as 'nucleophile-transferring agents' with the ultimate motivation to develop new synthetic tools. This first report focuses on the preparation of an axially chiral quinolinium salt 8. A preliminary investigation of these NAD(+) analogues as 'chiral amide-transferring agents' is reported herein. The synthesis of the desired quinolinium salt 8 was first attempted via a Friedlander approach. Given the poor reproducibility of this first synthetic route, a second strategy making use of an intramolecular nickel-catalyzed coupling was developed with success, furnishing the quinolinium salt 8 in 12% overall yield. The potential of the quinolinium salt 8 as a 'chiral amide-transferring agent' was then investigated. Regioselective 1,4-addition of benzylamine and piperidine produced, respectively, adducts 18a and 18b with high diastereoselectivity (de >95%). The resulting 'chiral masked-amide' 18b was reacted with various activated aryl esters affording the corresponding atropisomeric amide 20 with modest atropenantioselectivity (ee = 2-20%). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.004
• 作为产物：
  描述：

  乙烷,三氯氟- 、 邻硝基苯甲醛 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成 N-(2-硝基苯亚甲基)对甲苯胺
  参考文献：
  名称：

  溴和氰化溴化物发生器的集成，用于连续流动合成环胍。

  摘要：

  描述了一种利用膜分离技术从溴和氰化钾原位按需生成溴化氰（BrCN）的连续流工艺。为了规避元素溴的处理，储存和运输，可以选择在上游连接使用溴酸盐-溴化物共比例的连续溴发生器。通过实施在线FTIR技术，可以监控和量化BrCN的产生。通过将Br 2和BrCN发生器串联连接，每分钟可产生0.2 mmol BrCN，这相当于0.8  m BrCN在二氯甲烷中的溶液。模块化Br 2/ BrCN生成器用于合成多种生物学相关的五元和六元环状am和胍。该设置既可以完全集成的连续格式进行操作，也可以在半分批模式下（对于反应性结晶有利）操作。

  DOI：

  10.1002/anie.201708533

文献信息

• NOVEL TETRAHYDROQUINOLINE DERIVATIVES
  申请人：Feng Lichun

  公开号：US20120101127A1

  公开（公告）日：2012-04-26

  The present invention relates to compounds according to formula (I) and pharmaceutically acceptable salts or esters thereof, wherein R 1 to R 7 have the significance given herein. The compounds are activators of AMP-activated protein kinase (AMPK) and are useful in the treatment or prophylaxis of diseases that are related to AMPK regulation, such as obesity, dyslipidemia, hyperglycemia, type 1 or type 2 diabetes and cancers.

  本发明涉及按照式(I)的化合物及其药用可接受的盐或酯，其中R1至R7具有本文中给出的含义。这些化合物是AMP激活蛋白激酶（AMPK）的激活剂，并且在治疗或预防与AMPK调节相关的疾病方面具有用处，如肥胖、血脂异常、高血糖、1型或2型糖尿病和癌症。
• [EN] TETRAHYDROQUINOLINE DERIVATIVES USED AS AMPK ACTIVATORS<br/>[FR] DÉRIVÉS DE TÉTRAHYDROQUINOLINE UTILISÉS EN TANT QU'ACTIVATEURS D'AMPK
  申请人：HOFFMANN LA ROCHE

  公开号：WO2012052372A1

  公开（公告）日：2012-04-26

  A compound of formula (I), or a pharmaceutically acceptable salt or ester thereof, wherein R1 to R7 have the significance given in claim 1, can be used as a medicament.

  化合物的化学式（I），或其药学上可接受的盐或酯，其中R1至R7具有权利要求1中给定的含义，可用作药物。
• Reduction of nitro- and nitroso-compounds by tervalent phosphorus reagents. Part XI. A kinetic study of the effects of varying the reagent and the nitro-compound in the conversion of o-nitrobenzylideneamines to 2-substituted indazoles
  作者：Margaret-Ann Armour、J. I. G. Cadogan、David S. B. Grace

  DOI：10.1039/p29750001185

  日期：——

  A kinetic study of the effects of varying the phosphorus reagent and substituents in the nitro-compound in the reductive cyclisation of o-nitrobenzylideneamines to 2-substituted indazoles has been made. First-order rate constants vary from 8.2 to 52.2 × 10–5 s–1 for the triethyl phosphite-induced reduction of N-o-nitrobenzylideneanilines [o-NO2C6H4CHNC6H4Y; Y =p-MeO, p-Me, H, p-CI, p-Br, p-CO2Et, p-CN

  动力学研究了在邻硝基亚苄基胺还原成2-取代的吲唑的环化反应中改变硝基化合物中磷试剂和取代基的作用。一级速率常数从8.2变化至52.2×10 -5小号-1为的亚磷酸三乙酯诱导的减少ñ - ö -nitrobenzylideneanilines [ ø -NO 2 ç 6 ħ 4 CH NC 6 H ^ 4 ÿ; Y = p -MeO，p -Me，H，p -Cl，p -Br，p -CO 2等等，p -CN。p -NO 2，或ö ] -CI和Ñ -5-氯-2- nitrobenzylideneaniline，并略有不同的5至6×10 -5小号-1为ö -nitrobenzylideneamines [ ø -NO 2 ·C 6 H ^ 4 · CH NR; R = Me中，乙基，丙基我，或卜Ñ ]。这些反应的产物是相应的2-芳基-（芳基＝ C 6 H 4 Y）和2-烷基-（烷基＝ R）-吲唑。这
• A Facile One-Step Synthesis of 2-Arylindazoles via Reductive Cyclization of<i>N</i>-(2-nitroarylidene)amines
  作者：Wei Lin、Minghua Hu、Xian Feng、Chengpao Cao、Zhibin Huang、Daqing Shi

  DOI：10.1002/jhet.2221

  日期：2015.7

  A mild and efficient synthesis of 2‐arylindazole derivatives via the reductive cyclization of nitro‐aryl substrates mediated by a low‐valent titanium reagent (TiCl4/Sm/Et3N) has been developed. The attractive features of the current method include an N–N bond formation and the selective reduction of the C = N bond and nitro group, both of which were easily achieved in one‐pot by controlling the pH

  通过低价钛试剂（TiCl 4 / Sm / Et 3 N）介导的硝基芳基底物的还原环化，可以温和有效地合成2-芳基吲唑衍生物。当前方法的吸引人的特征包括N–N键的形成以及C = N键和硝基的选择性还原，通过控制反应混合物的pH值，很容易在一个锅中完成这两个操作。
• Facile synthesis of 4-substituted 1,2,4,5-tetrahydro-1,4-benzodiazepin-3-ones by reductive cyclization of 2-chloro-N-(2-nitrobenzyl)acetamides
  作者：Leandro D. Sasiambarrena、Ivan A. Barri、Guido G. Fraga、Rodolfo D. Bravo、Agustín Ponzinibbio

  DOI：10.1016/j.tetlet.2018.12.029

  日期：2019.1

  A facile and efficient method was developed for the synthesis of 1,2,4,5-tetrahydro-1,4-benzodiazepine-3-ones from 2-chloro-N-(2-nitrobenzyl)acetamides through a reductive cyclization using iron-ammonium chloride in ethanol–water in good yields. This method provides a simple approach to these benzodiazepine-3-ones which are of high value in the field of medicinal chemistry research.

  开发了一种简便有效的方法，可通过使用铁-铁的还原环化反应，从2-氯-N-（2-硝基苄基）乙酰胺合成1,2,4,5-四氢-1,4-苯并二氮杂-3-酮乙醇-水中的氯化铵收率高。该方法为这些在医学化学研究领域中具有高价值的苯并二氮杂-3-酮提供了一种简单的方法。