quinolin-8-yl diethylcarbamate

• 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: quinolin-8-yl diethylcarbamate
• 英文别名: quinolin-8-yl N,N-diethylcarbamate
• 化学式: C₁₄H₁₆N₂O₂
• 分子量: 244.293
• InChiKey: SQOGWLLYYCEMNN-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：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  8-羟基喹啉 、 N,N-二乙基甲酰胺 在 叔丁基过氧化氢 、 copper diacetate 作用下， 以 水 为溶剂， 以59%的产率得到quinolin-8-yl diethylcarbamate
  参考文献：
  名称：

  N，N-二取代甲酰胺和苯酚的铜催化交叉脱氢偶联：直接获得氨基甲酸酯

  摘要：

  AbstractAn efficient copper‐catalyzed protocol has been developed for the synthesis of carbamates from dialkylformamides and phenols possessing directing groups such as benzothiazole, quinoline and formyl at the ortho‐position. In this chelation assisted approach, CO bond formation takes place via a cross dehydrogenative coupling (CDC) between the formyl CH of dialkylformamide and phenolic OH in the presence of copper(II)acetate/aqueous tert‐butyl hydroperoxide. Under identical reaction conditions, salicylic acid derivatives underwent amidation with the carboxylic group rather than formamidation of the phenolic OH. The use of a cheap and environmentally benign catalyst along with the tolerance of a wide range of functional groups makes this an easy, phosgene‐free route to carbamates.magnified image

  DOI：

  10.1002/adsc.201400659

文献信息

• Design, synthesis and evaluation of quinoline-<i>O</i>-carbamate derivatives as multifunctional agents for the treatment of Alzheimer’s disease
  作者：Hongsong Chen、Jing Mi、Sen Li、Zhengwei Liu、Jing Yang、Rui Chen、Yujie Wang、Yujuan Ban、Yi Zhou、Wu Dong、Zhipei Sang

  DOI：10.1080/14756366.2023.2169682

  日期：2023.12.31

  rationally designed for treating Alzheimer’s disease (AD) by multi-target-directed ligands (MTDLs) strategy. The target compounds were synthesised and evaluated by AChE/BuChE inhibition and anti-inflammatory property. The in vitro activities showed that compound 3f was a reversible dual eeAChE/eqBuChE inhibitor with IC50 values of 1.3 µM and 0.81 µM, respectively. Moreover, compound 3f displayed good anti-inflammatory

  摘要 一系列新型喹啉-O-氨基甲酸酯衍生物被合理设计用于通过多靶点定向配体 (MTDLs) 策略治疗阿尔茨海默病 (AD)。合成目标化合物并通过 AChE/BuChE 抑制和抗炎特性进行评估。体外活性表明，化合物3f是一种可逆的双重ee AChE/eqBuChE 抑制剂，IC 50值分别为 1.3 µM 和 0.81 µM。此外，化合物3f通过减少 IL-6、IL-1β 和 NO 的产生显示出良好的抗炎特性。此外，化合物3f对 A β 25-35具有显着的神经保护作用-诱导的 PC12 细胞损伤。此外，化合物3f在人工胃肠液、体外肝微粒体和血浆中表现出良好的稳定性。此外，化合物3f可通过增加ACh水平改善AlCl 3诱导的斑马鱼AD模型。因此，化合物3f是一种很有前途的治疗 AD 的多功能药物。
• Ligand-Assisted Copper-Catalyzed Oxidative Cross-Coupling of Simple Phenols with Formamides for the Synthesis of Carbamates
  作者：Kallu Reddy、Nagireddy Reddy、Gadde Kumar、Pailla Kumar、M. Kantam

  DOI：10.1055/s-0034-1378519

  日期：——