3,3,8,10-tetramethyl-2,3-dihydro-1H-chromeno[2,3-b]quinolin-1-one | 1638853-53-8

• 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: 3,3,8,10-tetramethyl-2,3-dihydro-1H-chromeno[2,3-b]quinolin-1-one
• CAS: 1638853-53-8
• 化学式: C₂₀H₁₉NO₂
• 分子量: 305.376
• InChiKey: OKFBDBVTIVHSTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.51
• 重原子数：
  23.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  39.19
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1-氨基-3,5-二甲苯 在 potassium fluoride on basic alumina 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 22.5h， 生成 3,3,8,10-tetramethyl-2,3-dihydro-1H-chromeno[2,3-b]quinolin-1-one
  参考文献：
  名称：

  Efficient Synthesis of Novel Pyranoquinoline Derivatives from Simple Acetanilide Derivatives: Experimental and Theoretical Study of their Physicochemical Properties using DFT Calculations

  摘要：

  A convenient reaction of 2-chloroquinoline-3-carbaldehyde derivatives and dimedone in the presence of KF-Al2O3 for the synthesis of useful pyranoquinolines is described. Reasonable yields (41-50%), easily available starting materials and less expensive efficient catalyst are the key features of the present method. A mechanism was proposed for the reaction course. Attribution of the chemical shifts was made with the help of the density functional theory (DFT) calculations. The computed nuclear magnetic resonance (NMR) chemical shifts are in good agreement with available experimental data. The nucleus-independent chemical shift (NICS) values were used as quantitative measures for the relative aromatic character in pyranoquinolines. The calculated NICS values obtained for the phenyl group of pyranoquinoline compounds are smaller than that of benzene.

  DOI：

  10.5935/0103-5053.20140103

文献信息

• Efficient Synthesis and Evaluation of Antitumor Activities of Novel Functionalized 1,8-Naphthyridine Derivatives
  作者：Lei Fu、Xian Feng、Jian-Jun Wang、Zhan Xun、Jun-Die Hu、Juan-Juan Zhang、Yan-Wei Zhao、Zhi-Bin Huang、Da-Qing Shi

  DOI：10.1021/co500120b

  日期：2015.1.12

  An efficient synthesis of novel functionalized 1,8-naphthyridine and chromeno[2,3-b]quinoline derivatives via cascade reaction of 2-chloroquinoline-3-carbaldehyde and enaminones or cyclic 1,3-dicarbonyl compounds was developed. All of the 1,8-naphthyridine derivatives synthesized were evaluated for their antiproliferative properties in vitro against cancer cells and several compounds were found to have high activities.