N,N-diethyl-2-methylquinolin-4-amine | 82607-83-8

• 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,N-diethyl-2-methylquinolin-4-amine
• CAS: 82607-83-8
• 化学式: C₁₄H₁₈N₂
• mdl: MFCD28339683
• 分子量: 214.31
• InChiKey: GKCBSSBFVNHWSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.357
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-2-methylquinolin-4-amine 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 以89%的产率得到4-(diethylamino)quinoline-2-carbaldehyde
  参考文献：
  名称：

  使用喹啉官能化 NHC 作为定向和官能化基团，Ru/O2 催化氧化 C–H 活化/炔环化

  摘要：

  钌/O 2催化咪唑并[1,5- a ]喹啉-2-鎓盐与炔烃通过N-杂环卡宾引导的C-H活化发生氧化成环反应，得到π-共轭稠合咪唑[1,5-报道了a ]喹啉-2-鎓衍生物。分子氧已被探索作为一种经济且清洁的氧化剂以及金属氧化剂的替代品。当前的协议展示了广泛的底物范围，包括生物活性 (±)-α-生育酚衍生物。此外，大多数环状产品表现出很强的荧光特性，表明它们具有制造新型发光材料的潜力。

  DOI：

  10.1021/acs.orglett.4c00542
• 作为产物：
  描述：

  4-氯喹哪啶 、 二乙胺 在 苯酚 作用下， 生成 N,N-diethyl-2-methylquinolin-4-amine
  参考文献：
  名称：

  Ochiai; Nakamura, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1946, vol. 66, p. Ausg. B, S. 84

  摘要：

  DOI：

文献信息

• Microwave-Assisted Efficient Synthesis of 4-Substituted Amino-2-methylquinolines Catalyzed by p-Toluenesulfonic Acid
  作者：Xiao-qin Wang、Wen-jia Pan、Yuan-hong Cai、Xiao-yang Xie、Cui-ying Huang、Jia-yu Li、Wen-na Chen、Ming-hua He

  DOI：10.3987/com-16-13516

  日期：——

  A series of novel 4-subtituted amino-2-methylquinolines (3a-3o) were readily synthesized via the reaction of 4-chloro-2-methylquinoline with amines catalyzed by p-toluenesulfonic acid (TsoH) at 120 degrees C for 1 h under microwave-assisted organic synthesis (MAOS) condition. The yields of products 3a-3o were in range of 55-89%. This approach has advantages such as higher yield, shorter reaction time, lower costs, more convenience, and higher efficiency compared to the conventional method. The structures of the products were characterized by using H-1 NMR, C-13 NMR and HRMS. The reactivity of different amines was discussed.
• Ruthenium(II)‐Catalyzed Oxidative Annulation of Imidazo[1,5‐a]quinolin‐2‐iums Salts and Internal Alkynes via C−H Bond Activation
  作者：Monuranjan Konwar、Nitumoni Hazarika、Bikash Kumar Sarmah、Animesh Das

  DOI：10.1002/chem.202401133

  日期：2024.6.12

  Ruthenium(II)‐catalyzed synthesis of π‐conjugated fused imidazo[1,5‐a]quinolin‐2‐ium derivatives have been achieved via C−H activation of quinoline‐functionalized NHC (NHC=N‐heterocyclic carbene) and oxidative coupling with internal alkynes. The reaction occurred with high efficiency, broad substrate scope, tolerates a wide range of functional groups and utilized into a gram‐scale. Synthetic applications of the coupled product have been exemplified in the late‐stage derivatization of various highly functionalized scaffolds. Moreover, most of the annulated products exhibit intense fluorescence and have potential applications in optoelectronic devices. Mechanistic studies have provided insights into the spectroscopic characterization of key five‐membered ruthenacycle intermediate and Ru(0) sandwich species. Based on several control experiments, deuterium‐kinetic isotope effect, and thermodynamic activation parameters the mechanistic finding demonstrated that fused imidazo‐[1,5‐a]quinolin‐2‐ium C(2)−H bond cleavage is the rate‐determining step and ruling out the possibility of reductive elimination for controlling the rate of reaction.