2-(2'-pyridyl)-5,8-dimethoxyquinoline | 146830-16-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(2'-pyridyl)-5,8-dimethoxyquinoline
• 英文别名: 5,8-dimethoxy-2-(pyridin-2-yl)quinolone；5,8-Dimethoxy-2-pyridin-2-ylquinoline
• CAS: 146830-16-2
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: BSMOCBHQHRVDGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2'-pyridyl)-5,8-dimethoxyquinoline 在 ammonium cerium(IV) nitrate 作用下， 以 乙腈 为溶剂， 反应 0.75h， 生成 2-(2'-pyridyl)quinoline-5,8-quinone
  参考文献：
  名称：

  Design of quinolinedione-Based geldanamycin analogues

  摘要：

  Quinoline-5,8-dione-based compounds were designed from the structure of the geldanamycin-bound Hsp-90 active site. The active site model predicted that aromatic substituents should be present at the 2-position, to take advantage of a hydrophobic pocket, and amino substituents should be present at the 6- or 7-position. COMPARE analysis revealed that the LC50 profile of 2-phenyl-6-(2-chloroethylamino)quinoline-5,8-dione has the highest geldanamycin-like activity (0.74 correlation coefficient). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00650-4
• 作为产物：
  描述：

  3,6-二甲氧基-2-硝基苯甲醛 在 盐酸 、 氢氧化钾 、 铁粉 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 18.25h， 生成 2-(2'-pyridyl)-5,8-dimethoxyquinoline
  参考文献：
  名称：

  Incorporation of the quinoline-5,8-quinone moiety into polyaza cavities

  摘要：

  Silica gel supported nitric acid treatment of 2,5-dimethoxybenzaldehyde followed by reduction with iron powder provides 3,6-dimethoxy-2-aminobenzaldehyde. Friedlander condensation of this species with a variety of ketones and diketones leads to 5,8-dimethoxyquinoline derivatives which may be oxidized by ceric ammonium nitrate (CAN) and pyridine-2,6-dicarboxylic acid N-oxide (PDANO) to the corresponding quinones. The quinone functionality can be incorporated into larger cavities by a selective stepwise Friedlander approach and the CAN/PDANO oxidation appears to work preferentially for 5,8-dimethoxyquinoline.

  DOI：

  10.1021/jo00059a012

文献信息

• A facile one-pot synthesis of 2-(2-pyridyl)quinolines via Povarov reaction
  作者：Carmindo Ribeiro Borel、Luiz Claudio Almeida Barbosa、Célia Regina Álvares Maltha、Sergio Antonio Fernandes

  DOI：10.1016/j.tetlet.2014.12.016

  日期：2015.1

  An efficient synthesis of 2-(2-pyridyl)quinolines was achieved via a three-component Povarov reaction of aromatic aldehydes, anilines, and ethyl vinyl ether under boron trifluoride methyl etherate (BF3·O(CH3)2) acid catalysis. The developed methodology for the preparation of 2-(2-pyridyl)quinolines offers several advantages over previous methods including mild reaction conditions, easy work-up, a wide

  在三氟化硼甲醚硼酸（BF 3 ·O（CH 3）2）酸催化下，芳族醛，苯胺和乙基乙烯基醚的三组分Povarov反应实现了2-（2-吡啶基）喹啉的有效合成。与以前的方法相比，用于制备2-（2-吡啶基）喹啉的已开发方法具有多个优势，包括温和的反应条件，易于后处理，广泛的底物适用性以及高收率的产品。