5-amino-2-phenyl-3H-chromeno[4,3,2-de][1,6]naphthyridine-4-carbonitrile | 30455-85-7

• 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-phenyl-3H-chromeno[4,3,2-de][1,6]naphthyridine-4-carbonitrile
• 英文别名: 5-amino-2-phenyl-chromeno[4,3,2-de][1,6]naphthyridine-4-carbonitrile；5-amino-2-phenyl-chromeno[4,3,2-de][1,6]naphthyridine-4-carbonitrile；5-Amino-4-cyano-2-phenyl-benzopyrano<4,3,2-de><1,6>naphthyridin；11-amino-15-phenyl-8-oxa-10,14-diazatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9(17),10,12,14-octaene-12-carbonitrile
• CAS: 30455-85-7
• 化学式: C₂₁H₁₂N₄O
• 分子量: 336.352
• InChiKey: JGSZSIAPBJSHNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.52
• 重原子数：
  26.0
• 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

• 作为产物：
  描述：

  4-(2-Amino-1,3,3-tricyanoallyliden)-2-phenyl-4H-benzopyran 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 5-amino-2-phenyl-3H-chromeno[4,3,2-de][1,6]naphthyridine-4-carbonitrile
  参考文献：
  名称：

  van Allan,J.A. et al., Journal of Heterocyclic Chemistry, 1970, vol. 7, p. 1363 - 1368

  摘要：

  DOI：

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。
• Microwave-assisted Fe3O4 nanoparticles catalyzed synthesis of chromeno[1,6]naphthyridines in aqueous media
  作者：Anshu Dandia、Vijay Parewa、Shyam L. Gupta、Amit Sharma、Kuldeep S. Rathore、Amit Sharma、Astha Jain

  DOI：10.1016/j.catcom.2014.12.015

  日期：2015.2

  Fe3O4 nanocatalyst was prepared by co-precipitation method and characterized by XRD, FT-IR, TEM, VSM and BET analyses. The particles have an average size of 7 nm and possess highly open mesopores, moderate surface area, and uniform morphology with superparamagnetic behavior. Activity of catalyst was probed through the synthesis of chromeno[1,6]naphthyridines in water under microwave irradiation (MW) and it was about 7-fold higher as compared to conventional method. Nanocatalyst plays a dual role of catalyst as well as susceptor, and enhances the overall capacity to absorb MW. Fe3O4 NPs easily recovered by simple magnetic separation and recycled at least 5 times. (C) 2014 Elsevier B.V. All rights reserved.
• Novel fluorescence dyes based on entirely new chromeno[4,3,2-de][1,6]naphthyridine framework
  作者：Hai-Ying Wang、Jing-Jing Shi、Chao Wang、Xiao-Xiao Zhang、Yu Wan、Hui Wu

  DOI：10.1016/j.dyepig.2012.05.018

  日期：2012.11

  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.