N-(p-tolyl)quinolin-2-amine | 85291-41-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-(p-tolyl)quinolin-2-amine
• 英文别名: N-(4-methylphenyl)-2-quinolinamine；N-(4-methylphenyl)quinolin-2-amine
• CAS: 85291-41-4
• 化学式: C₁₆H₁₄N₂
• 分子量: 234.301
• InChiKey: IZMSCQMMRKVYSJ-UHFFFAOYSA-N

物化性质

• 熔点：
  135 °C(Solv: ethanol (64-17-5))
• 沸点：
  403.9±25.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯甲酸乙酯 、 N-(p-tolyl)quinolin-2-amine 在 甲烷磺酸 、 四磷十氧化物 作用下， 以15%的产率得到2-methyl-12-phenyldibenzo[b,g][1,8]naphthyridine
  参考文献：
  名称：

  Efficient Synthetic Route to Access Linear and Angular Dibenzonaphthyridines

  摘要：

  An efficient procedure has been proposed for the synthesis of linear and angular phenyl-substituted dibenzonaphthyridines from anilinoquinolines and benzoic acid in up to 85% yield using Eaton's reagent (a solution of phosphorous pentoxide in methanesulfonic acid) as condensing agent instead of polyphosphoric acid which previously afforded less than 50% yield of the same compounds. Apart from benzoic acid, ethyl benzoate and benzoyl chloride can be used in the synthesis of dibenzonaphthyridines according to the proposed procedure, but the yields are lower.

  DOI：

  10.1134/s1070428019100221
• 作为产物：
  描述：

  2-氨基苯乙烯 在 四氯化碳 、 三乙胺 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 49.0h， 生成 N-(p-tolyl)quinolin-2-amine
  参考文献：
  名称：

  C=C-conjugated carbodiimides as 2-aza dienes in intramolecular [4+2] cycloadditions. One-pot preparation of quinoline, .alpha.-carboline, and quinindoline derivatives

  摘要：

  Iminophosphoranes 2 derived from o-aminostyrenes react with aryl isocyanates to give the corresponding carbodiimides 13 which by thermal treatment at 160-degrees-C undergo 6-pi-electrocyclization to give quinoline derivatives 14. However, the reaction with styryl isocyanates leads to alpha-carbolines 19 through the intermediate carbodiimides 15 which undergo a tandem intramolecular hetero-Diels-Alder cycloaddition/aromatization process to give 19. Similarly, related alpha-carbolines 20-22 can be obtained from the reaction of iminophosphoranes derived from ortho-substituted anilines containing an unsaturated side chain with styryl isocyanates. Iminophosphorane 6a, derived from o-butadienylaniline, and related 10 and 12 react with aryl isocyanates under the same reaction conditions to give quinindoline derivatives 25-27, respectively. Finally, iminophosphoranes 2 and 6 by reaction with ketenes lead directly to quinolines 32 and benzo[b]carbazoles 33, respectively.

  DOI：

  10.1021/jo00029a026

文献信息

• Deoxygenative Amination of Azine-<i>N</i>-oxides with Acyl Azides via [3 + 2] Cycloaddition
  作者：Dongeun Kim、Prithwish Ghosh、Na Yeon Kwon、Sang Hoon Han、Sangil Han、Neeraj Kumar Mishra、Saegun Kim、In Su Kim

  DOI：10.1021/acs.joc.9b03173

  日期：2020.2.21

  an isocyanate from the starting acyl azide via a Curtius rearrangement can trigger a [3 + 2] dipolar cycloaddition of polar N-oxide fragments to generate the aminated azine derivative. The applicability of this method is highlighted by the late-stage and sequential amination reactions of complex bioactive compounds, including quinidine and fasudil. Moreover, the direct transformation of aminated azines

  描述了一种无过渡金属的嗪-N-氧化物与酰基叠氮化物的脱氧CH胺化反应。通过库尔修斯重排从起始酰基叠氮化物初步形成异氰酸酯可以触发极性N-氧化物片段的[3 + 2]双极性环加成反应，从而生成胺化的嗪衍生物。复杂的生物活性化合物（包括奎尼丁和法舒地尔）的后期和顺序胺化反应突出了该方法的适用性。此外，将胺化嗪直接转化为各种生物活性的N-杂环说明了这种新开发的方案的重要性。
• 아민화된 아진의 신규한 제조방법
  申请人：Research ＆ Business Foundation SUNGKYUNKWAN UNIVERSITY 성균관대학교산학협력단(220050013604) BRN ▼101-82-12009

  公开号：KR20210088789A

  公开（公告）日：2021-07-15

  본 발명은 4중 연속 고리 화합물의 신규한 제조방법에 관한 것으로, 본 발명의 제조방법에 따르면, 기존의 카르보닐기 또는 히드록시기를 보호하기 위한 단위구조로 활용된 아세탈의 신규한 반응성을 이용하여, 의약품의 핵심골격으로 알려진 4중 연속고리 약물 분자구조를 합성함으로써, 다양한 의약화학 및 제약 공정 연구에 유용하게 적용될 것으로 기대된다.

  This invention relates to a novel method for the production of a quadruple consecutive ring compound. According to the production method of this invention, by utilizing the novel reactivity of acetal, which has been used as a unit structure to protect existing carbonyl or hydroxyl groups, it is expected to be applied beneficially in various pharmaceutical chemistry and pharmaceutical process research by synthesizing the molecular structure of a quadruple consecutive ring drug known as the core skeleton of a drug.
• Organonickel complexes encumbering bis-imidazolylidene carbene ligands: Synthesis, X-ray structure and catalytic insights on Buchwald-Hartwig amination reactions
  作者：Muthukumaran Nirmala、Gandhi Saranya、Periasamy Viswanathamurthi、Roberta Bertani、Paolo Sgarbossa、Jan Grzegorz Malecki

  DOI：10.1016/j.jorganchem.2016.12.029

  日期：2017.3

  bis(diimidazolylidene) NHC ligands and two non coordinating bromide counter ions in tetradentate C4 fashion. A survey of their catalytic activity in Buchwald−Hartwig amination has been performed. The newly synthesized complexes also catalyzed the amination of aryl chlorides in the presence of KOtBu. Various aryl chlorides and amines can react smoothly to give the corresponding aminated products in moderate to high yields

  合成了四种新的配位均化双（二咪唑基亚甲基）镍（II）配合物（C1和C2），并通过元素分析，NMR（1 H和13 C）以及ESI-质谱进行了表征。通过单晶X射线衍射分析鉴定了配合物C1的分子结构，结果表明该配合物具有扭曲的方形平面几何形状，四齿C中具有螯合双（二咪唑基亚甲基）NHC配体和两个非配位溴化物抗衡离子。4时尚。已经对其在布赫瓦尔德-哈特维格胺胺化中的催化活性进行了调查。新合成的配合物还可以在KO t存在下催化芳基氯的胺化反应。卜 各种芳基氯化物和胺可以平稳反应，以中等至高收率得到相应的胺化产物。反应范围包括电子变化的芳基氯和含氮杂芳基氯，包括吡啶和喹啉衍生物。在最佳反应条件下，仲胺和伯胺均具有良好的耐受性。
• [EN] GLYCINE B ANTAGONISTS<br/>[FR] ANTAGONISTES DE LA GLYCINE B
  申请人：MERZ PHARMA GMBH & CO KGAA

  公开号：WO2010037533A1

  公开（公告）日：2010-04-08

  The invention relates to quinoline derivatives as well as their pharmaceutically acceptable salts. The invention further relates to a process for the preparation of such compounds. The compounds of the invention are glycine B antagonists and are therefore useful for the control and prevention of various disorders, including neurological disorders.

  该发明涉及喹啉衍生物及其药用盐。该发明还涉及一种制备这种化合物的方法。该发明的化合物是甘氨酸B拮抗剂，因此对于控制和预防各种疾病，包括神经系统疾病，非常有用。
• Insights on Bimetallic Micellar Nanocatalysis for Buchwald–Hartwig Aminations
  作者：Tharique N. Ansari、Armand Taussat、Adam H. Clark、Maarten Nachtegaal、Scott Plummer、Fabrice Gallou、Sachin Handa

  DOI：10.1021/acscatal.9b02622

  日期：2019.11.1

  their linkage with the activated carbon surface is revealed by XAS analysis. Control NMR experiments revealed the binding of the ligand with both Cu and Pd, and all phosphine molecules are under the same environment. In addition to NMR and XAS analysis, the catalyst is characterized by SEM, HRTEM, XPS, and TGA. Reactions are highly reproducible at variable scales. Environmentally benign, proline-based

  胶束布赫瓦尔德-哈特维格胺胺化的纳米催化剂已经开发，充分表征并应用于多种底物上。该催化剂在环境条件下稳定至少六个月。催化剂在几个循环后仍保持其活性，并且如NMR光谱所证实的，其结构保持完整。31揭示了磷化氢配体使Pd纳米颗粒与Cu缔合通过XAS分析揭示了P NMR光谱及其与活性炭表面的联系。对照NMR实验表明，配体与Cu和Pd均结合，所有膦分子均处于同一环境中。除了NMR和XAS分析之外，该催化剂还通过SEM，HRTEM，XPS和TGA进行表征。反应在可变规模下可高度重现。环境友好的脯氨酸基两亲物PS-750-M对于催化活性至关重要，该催化活性是在温和条件下以水为反应介质的条件下实现的。这些条件的固有可持续性，再加上通过催化剂和反应介质的强健循环可实现的低E因子，证明了该技术的巨大实用性。