5-amino-2-(4-bromophenyl)-chromeno[4,3,2-de][1,6]naphthyridine-4-carbonitrile | 1204405-90-2

• 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: 5-amino-2-(4-bromophenyl)-chromeno[4,3,2-de][1,6]naphthyridine-4-carbonitrile
• CAS: 1204405-90-2
• 化学式: C₂₁H₁₁BrN₄O
• 分子量: 415.249
• InChiKey: IRKOKNAHFSSXFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.29
• 重原子数：
  27.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.82
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-amino-2-(4-bromophenyl)-chromeno[4,3,2-de][1,6]naphthyridine-4-carbonitrile 、 苯硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 72.0h， 以85%的产率得到5-amino-2-(biphenyl-4-yl)chromeno[4,3,2-de][1,6]naphthyridine-4-carbonitrile
  参考文献：
  名称：

  Novel fluorescence dyes based on entirely new chromeno[4,3,2-de][1,6]naphthyridine framework

  摘要：

  A series of entirely new framework chromeno[4,3,2-de][1,6]naphthyridine derivatives containing triphenylamine groups have been carefully designed and prepared in good yields using the Pd(0) catalyzed Suzuki couplings reactions. The relationship of photoluminescence property and structure of these compounds was systematically investigated via thermogravimetric analyzer, UV-vis, fluorescence and electrochemical analyzer. The HOMO and LUMO distributions of these compounds were calculated by density functional theory (DFT) (B3LYP; 6-31G*) method. These compounds exhibited high fluorescence quantum yields, desirable HOMO levels and high thermal stability, indicating that the combination of chromeno[4,3,2-de][1,6]naphthyridine and triphenylamine could be an efficient means to enhance hole-transporting ability and fluorescent quantum yield. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.05.018
• 作为产物：
  描述：

  2'-羟基苯乙酮 、 对溴苯甲醛 、 丙二腈 在 silica gel 作用下， 以 水 为溶剂， 反应 2.0h， 以76%的产率得到5-amino-2-(4-bromophenyl)-chromeno[4,3,2-de][1,6]naphthyridine-4-carbonitrile
  参考文献：
  名称：

  硅胶催化的一锅水合成及5-氨基-2-芳基-3 H-苯并[4,3,2- de ] [1,6]萘吡啶-4-甲腈和5-氨基的荧光性质研究-2-芳基-3 H-喹啉基[4,3,2- de ] [1,6]萘啶-4-腈

  摘要：

  5-氨基-2-芳基- 3所述的硅胶催化合成ħ -chromeno [4,3,2 DE ] [1,6]萘啶-4-腈和5-氨基-2-芳基-3- ħ -在含水介质中，丙二腈与取代的2-羟基苯乙酮（或2-氨基苯乙酮）和芳香醛进行一锅级联反应，即可轻松实现喹啉基[4,3,2- de ] [1,6]萘啶-4-腈。基于电喷雾电离质谱（ESI-MS）的机理研究结果表明，丙二腈在该转化过程中发挥了双重作用。断裂13个键，并构建12个新键，形成5-氨基-2-芳基-3 H -chromeno [4,3,2- de] [1,6]萘啶-4-腈，而仅去除了2个H 2 O分子。荧光性质筛选显示五种新化合物具有高荧光量子产率。

  DOI：

  10.1021/cc9001179

文献信息

• Fe ₃ O ₄ @SiO ₂ @sulfated boric acid as superparamagnetic and recyclable nanocatalyst‐assisted, one‐pot, <i>pseudo</i> four‐component synthesis of 5‐amino‐2‐aryl‐3 <i>H</i> ‐chromeno[4,3,2‐ <i>de</i> ][1,6]naphthyridine‐4‐carbonitrile derivatives
  作者：Zeynab Khosravi、Hadi Mohammadi、Hamid Reza Shaterian

  DOI：10.1002/jccs.201900044

  日期：2019.12

  Fe3O4@SiO2@Sulfated boric acid as a green, recyclable, and acidic solid catalyst in the synthesis of chromeno[4,3,2‐de][1,6]naphthyridine derivatives has been studied. Chromeno[4,3,2‐de][1,6]naphthyridine derivatives via a pseudo four‐component reaction from aromatic aldehydes (1 mmol), malononitrile (2 mmol), and 2′‐hydroxyacetophenone in the presence of Fe3O4@SiO2@Sulfated boric acid (0.004 g) as a nanocatalyst

  超顺磁性纳米催化剂Fe 3 O 4 @SiO 2 @硫酸化硼酸作为绿色，可循环利用和酸性固体催化剂，在合成铬诺[4,3,2- de ] [1,6]萘啶衍生物中具有被研究了。在Fe 3 O存在下，由芳香醛（1 mmol），丙二腈（2 mmol）和2'-羟基苯乙酮通过假四组分反应生成Chromeno [4,3,2- de ] [1,6]萘啶衍生物4 @SiO 2在80℃下，在3mL作为绿色溶剂的水中合成了作为纳米催化剂的硫酸化硼酸（0.004g）。该方法的优点是：在较短的反应时间内可以提高产品收率，催化剂的回收率和重复使用性易于操作，并且后处理程序也很容易。纳米催化剂被重复使用至少六次。纳米催化剂在反应中保持其稳定性，并且在可重复使用之后，其易于通过外部磁体与反应分离。
• Synthesis and characteristics of novel fluorescence dyes based on chromeno[4,3,2-de][1,6]naphthyridine framework
  作者：Haiying Wang、Jingjing Shi、Chao Wang、Xiaoxiao Zhang、Lingling Zhao、Yu Wan、Hui Wu

  DOI：10.1016/j.saa.2012.10.075

  日期：2013.2

  A series of entirely new framework chromeno[4,3,2-de][1,6]naphthyridine derivatives containing carbazole groups have been carefully designed and prepared. The relationship of photoluminescence property and structure of these compounds was systematically investigated via UV-vis, fluorescence and electrochemical analyzer. The HOMO and LUMO distributions of these compounds were calculated by density functional theory (DFT) (B3LYP; 6-31G*) method. These compounds exhibited high fluorescence quantum yields, desirable HOMO levels and high thermal stability, indicating that the combination of chromeno[4,3,2-de][1,6]naphthyridine and carbazole could be an efficient means to enhance hole-transporting ability and fluorescent quantum yield. (C) 2012 Elsevier B.V. All rights reserved.