8-(4-bromobenzylidene)-4-(4-bromophenyl)-6-methyl-2-(phenylamino)-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carbonitrile | 1195986-36-7

• 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: 8-(4-bromobenzylidene)-4-(4-bromophenyl)-6-methyl-2-(phenylamino)-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carbonitrile
• CAS: 1195986-36-7
• 化学式: C₂₉H₂₂Br₂N₄
• 分子量: 586.328
• InChiKey: AVSJKMWALGLXMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.87
• 重原子数：
  35.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  51.95
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3,5-bis-(4-bromobenzylidene)-1-methylpiperidin-4-one 、 苯胺 、 丙二腈 在 ferric oxide nanoparticles on sulfonic acid functionalized graphene oxide 作用下， 以 neat (no solvent) 为溶剂， 反应 0.83h， 以93%的产率得到8-(4-bromobenzylidene)-4-(4-bromophenyl)-6-methyl-2-(phenylamino)-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carbonitrile
  参考文献：
  名称：

  磁性氧化石墨烯固定的磺酸作为合成N-芳基-2-氨基-1,6-萘啶的新型纳米催化剂

  摘要：

  磺酸功能化的磁性氧化石墨烯（Fe 3 O 4 -GO-SO 3 H）被用作一种新的可回收纳米催化剂，用于在无溶剂条件下一锅法合成N-芳基-2-氨基-1,6-萘啶衍生物。可以容易地通过外部磁体从反应混合物中回收催化剂，并且即使在4次运行后，活性也不会显着降低地重复使用。该纳米催化剂显示出比其他市售磺酸催化剂更好的活性。

  DOI：

  10.1002/jccs.201300167

文献信息

• Diversity Synthesis of N-Substituted 2-Amino-1,6-naphthyridine Derivatives under Microwave Irradiation
  作者：Zheng-Guo Han、Chun-Bao Miao、Feng Shi、Ning Ma、Ge Zhang、Shu-Jiang Tu

  DOI：10.1021/cc900030e

  日期：2010.1.11

  A sequential three-component reaction of 3,5-diarylidenepiperidin-4-one, malononitrile, and amine (such as aromatic amine, cyclopropanamine, and NH4OAc) in acetic acid under microwave irradiation has been developed. In this one-pot reaction, a series of new N-substituted 2-amino-1,6-naphthyridine derivatives were synthesized with excellent yields. This method has the advantages of operational simplicity and increased safety for small-scale fast synthesis of N-aryl 2-amino-1,6-naphthyridines for biomedical screening.
• (α-Fe2O3)-MCM-41-SO3H as a novel magnetic nanocatalyst for the synthesis of N-aryl-2-amino-1,6-naphthyridine derivatives
  作者：Shahnaz Rostamizadeh、Mohammad Azad、Nasrin Shadjou、Mohammad Hasanzadeh

  DOI：10.1016/j.catcom.2012.04.013

  日期：2012.8

  The new (alpha-Fe2O3)-MCM-41-SO3H catalyst was prepared directly through the reaction of chlorosulfonic acid with silica-coated nanoparticles (alpha-Fe2O3)-MCM-41 and used as a magnetically recyclable catalyst for an efficient one-pot synthesis of N-aryl-2-amino-1,6-naphthyridine derivatives. The catalyst with 10 wt% of loaded iron oxide nanoparticles could be recovered from the reaction mixture by an external magnet and reused without significant decrease in activity even after 5 runs. This new prepared catalyst exhibited better activities to other commercially available sulfonic acid catalysts. (C) 2012 Elsevier B.V. All rights reserved.