N-(4-甲氧基苯基)-4-甲基喹啉-2-胺 | 67837-41-6

• 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
• 中文名称: N-(4-甲氧基苯基)-4-甲基喹啉-2-胺
• 英文名称: (4-methoxyphenyl)(4-methylquinolin-2-yl)amine
• 英文别名: N-(4-methoxyphenyl)-4-methylquinolin-2-amine；2-(4-methoxyanilino)-4-methylquinoline；(4-methoxy-phenyl)-(4-methyl-[2]quinolyl)-amine；(4-Methoxy-phenyl)-(4-methyl-[2]chinolyl)-amin
• CAS: 67837-41-6
• 化学式: C₁₇H₁₆N₂O
• 分子量: 264.327
• InChiKey: OMQXICZOJACACB-UHFFFAOYSA-N

物化性质

• 熔点：
  129 °C
• 沸点：
  428.8±40.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)
• 溶解度：
  12.6 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  34.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-甲氧基苯基)-4-甲基喹啉-2-胺 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 以65%的产率得到2-Methoxy-11-methyl-dibenzo[b,g][1,8]naphthyridine
  参考文献：
  名称：

  Kidwai; Kohli, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 3, p. 248 - 249

  摘要：

  DOI：
• 作为产物：
  描述：

  (2-Isopropenyl-phenyl)-(4-methoxy-phenyl)-carbodiimide 以 甲苯 为溶剂， 反应 24.0h， 生成 N-(4-甲氧基苯基)-4-甲基喹啉-2-胺
  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

• Catalyst-Free Synthesis of 2-Anilinoquinolines and 3-Hydroxyquinolines via Three-Component Reaction of Quinoline <i>N</i>-Oxides, Aryldiazonium Salts, and Acetonitrile
  作者：Ankit Kumar Dhiman、Devesh Chandra、Rakesh Kumar、Upendra Sharma

  DOI：10.1021/acs.joc.9b00739

  日期：2019.6.7

  microwave-assisted, catalyst-free, three-component synthesis of various 2-anilinoquinolines from quinoline N-oxides and aryldiazonium salts in acetonitrile under microwave irradiation is reported. This reaction utilizes acetonitrile as a single nitrogen source and involves the formation of two new C–N bonds via the formal [3 + 2] cycloaddition reaction. In the case of 2-substituted quinolines, 3-hydroxyquinoline

  据报道，在微波辐射下，由乙腈中的喹啉N-氧化物和芳基重氮盐快速微波辅助，无催化剂的三组分合成各种2-苯胺基喹啉。该反应利用乙腈作为单一氮源，并通过正式的[3 + 2]环加成反应形成两个新的C–N键。在2-取代的喹啉的情况下，观察到3-羟基喹啉是主要产物，这是因为氧原子从N-氧化物向喹啉的C3位置转移了1,3 。
• Cu-Catalyzed Aerobic Oxidative Cyclizations of 3-<i>N</i>-Hydroxyamino-1,2-propadienes with Alcohols, Thiols, and Amines To Form α-<i>O</i>-,<i>S</i>-, and<i>N</i>-Substituted 4-Methylquinoline Derivatives
  作者：Pankaj Sharma、Rai-Shung Liu

  DOI：10.1002/chem.201406317

  日期：2015.3.16

  one‐pot, two‐step synthesis of α‐O‐, S‐, and N‐substituted 4‐methylquinoline derivatives through Cu‐catalyzed aerobic oxidations of N‐hydroxyaminoallenes with alcohols, thiols, and amines is described. This reaction sequence involves an initial oxidation of N‐hydroxyaminoallenes with NuH (Nu=OH, OR, NHR, and SR) to form 3‐substituted 2‐en‐1‐ones, followed by Brønsted acid catalyzed intramolecular cyclizations

  描述了通过醇，硫醇和胺与铜催化的N-羟基氨基丙烯的好氧氧化反应，一锅，两步合成α- O-，S-和N-取代的4-甲基喹啉衍生物。该反应顺序涉及N的初始氧化与NuH（Nu = OH，OR，NHR和SR）形成的γ-羟基氨基丙烯形成3个取代的2 en 1 -1，然后由Brønsted酸催化所得产物的分子内环化。我们的机理分析表明，反应是通过自由基类型的机理进行的，而不是通过典型的硝酮中间体途径进行的。这种新的铜催化反应的实用性通过其对几种2-氨基-4-甲基喹啉衍生物的合成的适用性得到了证明，已知这些衍生物是几种生物活性分子的关键前体。
• Synthesis of Quinolines and 2‐Functionalized Quinolines by Difluorocarbene Incorporation
  作者：Ben‐Jie Jiang、Song‐Lin Zhang

  DOI：10.1002/adsc.202200263

  日期：2022.7.5

  2-SeH quinolines. In the presence of a second nucleophile such as anilines, competing nucleophilic addition of anilines to the selenoisocyanate is preferred, generating selenourea intermediate. Further nucleophilic addition of the ortho-alkenyl to selenourea followed by elimination of H2Se produces 2-aminoquinolines. This allows one-step multi-component modular preparation of various C2-functionalized

  开发了一种通用方法，以允许在二氟卡宾前体存在下从邻-烯基苯胺从头构建喹啉和 C2 官能化喹啉。该方法利用伯苯胺与二氟卡宾缩合原位生成异氰化物的关键反应性。随后通过相邻的烯基α-加成异氰化物构建喹啉环。此外，当存在二氟卡宾前体和硒的组合时，通过邻位亲核加成，初步生成硒代异氰酸酯中间体。-烯基产生 2-SeH 喹啉。在第二亲核试剂如苯胺的存在下，苯胺与硒代异氰酸酯的竞争性亲核加成是优选的，生成硒脲中间体。邻位-烯基进一步亲核加成到硒脲，然后消除 H 2 Se 产生 2-氨基喹啉。这允许从容易获得的起始化合物一步多组分模块化制备各种 C2 官能化喹啉。该方法显示出良好的产率、范围和化学选择性。它操作方便且友好，无需处理令人不快的异氰化物。可利用二氟卡宾使伯胺转化为异氰化物来开发其他有趣的反应。
• 242. 2-Anilinolepidine derivatives
  作者：O. G. Backeberg

  DOI：10.1039/jr9330001031

  日期：——
• Sharma, N. D.; Kumar, Santosh; Bakore, P. V., Journal of the Indian Chemical Society, 1987, vol. 64, # 8, p. 481 - 482
  作者：Sharma, N. D.、Kumar, Santosh、Bakore, P. V.、Joshi, B. C.

  DOI：——

  日期：——