N-(4-methylphenyl)quinolin-4-amine | 21626-51-7

• 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-(4-methylphenyl)quinolin-4-amine
• 英文别名: 4-(4-methylanilino)quinoline；quinolin-4-yl-p-tolyl-amine
• CAS: 21626-51-7
• 化学式: C₁₆H₁₄N₂
• 分子量: 234.301
• InChiKey: SROJXUIEUGMDRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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

• 作为产物：
  描述：

  4-氯-3-喹啉磺酸 在 硫酸 、 三乙胺 作用下， 以 水 为溶剂， 反应 15.0h， 生成 N-(4-methylphenyl)quinolin-4-amine
  参考文献：
  名称：

  Synthesis of 4-Amino-3-quinolinesulfonic Acids and 4-Aminoquinolines

  摘要：

  The hydrolysis of 4-chloro-3-quinolinesulfonyl chloride (1) gives 4-chloro-3-quinolinesulfonic acid (2) or 1,4-dihydro-4-oxo-3-quinolinesulfonic acid (3). Compound (2) reacts with primary and secondary aliphatic or primary aromatic amines to give 4-amino-3-quinolinesulfonic acids (4). Desulfonation of quinolinesulfonic acids (2,3,4) yields 4(1H)-quinolinone or 4-aminoquinolines (5).

  DOI：

  10.3987/com-97-8003

文献信息

• [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。
• QUINOLINE DERIVATIVES FOR MODULATING DNA METHYLATION
  申请人：Phiasivongsa Pasit

  公开号：US20090285772A1

  公开（公告）日：2009-11-19

  Quinoline derivatives, particularly 4-anilinoquinoline derivatives, are provided. Such quinoline derivatives can be used for modulation of DNA methylation, such as effective inhibition of methylation of cytosine at the C-5 position, for example via selective inhibition of DNA methyltransferase DNMT1. Methods for synthesizing numerous 4-anilinoquinoline derivatives and for modulating DNA methylation are provided. Also provided are methods for formulating and administering these compounds or compositions to treat conditions such as cancer and hematological disorders.

  提供了喹啉衍生物，特别是4-苯胺基喹啉衍生物。这样的喹啉衍生物可用于调节DNA甲基化，例如通过选择性抑制DNA甲基转移酶DNMT1，有效抑制C-5位置的胞嘧啶甲基化。提供了合成多种4-苯胺基喹啉衍生物和调节DNA甲基化的方法。还提供了制剂和给药这些化合物或组合物以治疗癌症和血液疾病的方法。
• GLYCINE B ANTAGONIST
  申请人：Henrich Markus

  公开号：US20110190342A1

  公开（公告）日：2011-08-04

  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.

  本发明涉及喹啉衍生物及其药学上可接受的盐。本发明还涉及制备这种化合物的过程。本发明的化合物是甘氨酸B拮抗剂，因此对控制和预防各种疾病，包括神经系统疾病，非常有用。
• Aerobic Dehydrogenative Aromatization in the Preparation of 4-Aminoquinoline Derivatives by Synergistic Pd/Cu Catalysis
  作者：Fei Chen、Huidan Geng、Chun Li、Jianta Wang、Bing Guo、Lei Tang、Yuan-Yong Yang

  DOI：10.1021/acs.joc.3c01400

  日期：2023.11.17

  The 4-aminoquinoline moiety is widely present in various bioactive compounds and marketed drugs, while the preparation of this target structure relies heavily on the amination of 4-chloroquinolines. Herein, an atom and step economic procedure was developed based on an aerobic dehydrogenative aromatization strategy. Unlike the well-known palladium-catalyzed dehydrogenative aromatization of cyclohexanones

  4-氨基喹啉部分广泛存在于各种生物活性化合物和市售药物中，而该目标结构的制备很大程度上依赖于4-氯喹啉的胺化。在此，基于有氧脱氢芳构化策略开发了原子和步骤经济程序。与众所周知的钯催化环己酮与胺的脱氢芳构化不同，协同 Pd/Cu 催化对于 2,3-二氢喹啉-4(1 H )-one 类型的底物至关重要。在优化条件下，一系列芳香族/脂肪族胺和2,3-二氢喹啉-4(1H ) -酮偶联，以中等到高收率得到相应的4-氨基喹啉产物，并应用当前的方法还展示了上市药物的制备和后期多样化。
• From Amides to Amidines:  Preparations of Imidoylbenzotriazoles and Arylaminoheterocycles
  作者：Alan R. Katritzky、Tian-Bao Huang、Michael V. Voronkov

  DOI：10.1021/jo0013397

  日期：2001.2.1