6-phenyl-1,2,3,4-tetrahydro-1,5-naphthyridine | 791856-65-0

• 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: 6-phenyl-1,2,3,4-tetrahydro-1,5-naphthyridine
• CAS: 791856-65-0
• 化学式: C₁₄H₁₄N₂
• 分子量: 210.279
• InChiKey: OKJFWRMUUFIQSU-UHFFFAOYSA-N

物化性质

• 熔点：
  91-93 °C
• 沸点：
  383.6±31.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-(S)-1-(2,3-epoxypropyl)-6-(4-methoxyphehyl)-1,2,3,4-tetrahydro-1,5-naphthyridine 、 6-phenyl-1,2,3,4-tetrahydro-1,5-naphthyridine 在 ytterbium(III) triflate 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 生成
  参考文献：
  名称：

  1,2,3,4-Tetrahydro-1,5-naphthyridines and related heterocyclic scaffolds: exploration of suitable chemistry for library development

  摘要：

  The chemistry of 1,2,3,4-tetrahydro-1,5-naphthyridines and 2,3,4,5-tetrahydro-1H-pyrido[3,2-b] azepines has been explored with the goal of discovering reactions at N1 suitable for library development. Epoxide openings, Pd-catalyzed N-arylations, DEPBT-promoted acylations, and urea formation through the reaction with isocyanates were all successful. The epoxide opening chemistry using homochiral epichlorohydrin followed by epoxide reclosure and a second nucleophilic opening led to the preparation of a small 24-membered library. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.003
• 作为产物：
  描述：

  3-(3-imidazol-1-ylpropyl)-5-phenyl-1,2,4-triazine 在 2,6-二叔丁基-4-甲基苯酚 、 triisopropylbenzene 作用下， 反应 7.0h， 以81%的产率得到6-phenyl-1,2,3,4-tetrahydro-1,5-naphthyridine
  参考文献：
  名称：

  咪唑与1,2,4-三嗪的分子内电子逆需求Diels-Alder反应：通往1,2,3,4-四氢-1,5-萘啶和相关杂环的新途径

  摘要：

  咪唑和1,2,4-三嗪之间的分子内逆电子需求的Diels-Alder反应由三亚甲基系链从咪唑N1位置连接到三嗪C3，从而以极好的收率进行生产1,2,3,4-四氢-1，5-萘啶。该反应通过环加成反应进行，随后损失氮气，然后逐步损失腈。使用四亚甲基系链的类似分子内环加成反应也以可接受的收率得到了2,3,4,5-四氢-1 H-吡啶并[3,2- b ]氮杂。微波辐射也可以促进产生四氢-1，5-萘啶的反应。

  DOI：

  10.1021/jo040193z

文献信息

• Synthesis of <i>meta</i> -Functionalized Pyridines by Selective Dehydrogenative Heterocondensation of β- and γ-Amino Alcohols
  作者：Toni Hille、Torsten Irrgang、Rhett Kempe

  DOI：10.1002/anie.201610071

  日期：2017.1.2

  concepts to synthesize meta‐functionalized pyridines. First, diols and amines were linked to β‐amino alcohols, which can then undergo a selective dehydrogenative heterocondensation with γ‐amino alcohols. Iridium catalysts stabilized by PN5P pincer ligands that were developed in our laboratory mediate the reactions most efficiently. All of the 3‐aminopyridines that we describe in this paper have been synthesized

  将醇转化为重要化合物类别的新反应变得越来越重要，因为它们的发展有助于保护我们的化石碳原料并减少CO 2排放。催化醇转化的两个关键概念是借用氢或氢的自动转移和无受体的脱氢缩合反应。在这里，我们结合了两个概念来合成间功能化的吡啶。首先，将二醇和胺与β-氨基醇连接，然后可以与γ-氨基醇进行选择性脱氢杂缩反应。PN 5稳定的铱催化剂我们实验室开发的P钳配体最有效地介导了反应。所有3氨基吡啶，我们在本文中描述的被合成的第一次，强调这种方法的创新程度和与该合成相关的问题元-功能化吡啶。
• Ruthenium-Catalyzed Straightforward Synthesis of 1,2,3,4-Tetrahydronaphthyridines via Selective Transfer Hydrogenation of Pyridyl Ring with Alcohols
  作者：Biao Xiong、Ya Li、Wan Lv、Zhenda Tan、Huanfeng Jiang、Min Zhang

  DOI：10.1021/acs.orglett.5b01976

  日期：2015.8.21

  Through a ruthenium-catalyzed selective hydrogen transfer coupling reaction, a novel straightforward synthesis of 1,2,3,4-tetrahydronaphthyridines from o-amino-pyridyl methanols and alcohols has been developed. The synthetic protocol proceeds in an atom- and step-economic fashion together with the advantages of operational simplicity, broad substrate scope, production of water as the only byproduct, and no need for external reducing reagents such as high pressure H-2 gas, offering a highly practical approach for accessing this type of structurally unique products.