6,7-dimethyl-1,2,3,4-tetrahydro-1,5-naphthyridine | 198549-23-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 6,7-dimethyl-1,2,3,4-tetrahydro-1,5-naphthyridine
• 英文别名: 1,2,3,4-tetrahydro-6,7-dimethyl-1,5-naphthyridine
• CAS: 198549-23-4
• 化学式: C₁₀H₁₄N₂
• mdl: MFCD18802926
• 分子量: 162.235
• InChiKey: JRZUQBSXSSZHGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  6,7-dimethyl-1,2,3,4-tetrahydro-1,5-naphthyridine 在 sodium hydride 、 ytterbium(III) triflate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (+)-(S)-1-(2,3-epoxypropyl)-6,7-dimethyl-1,2,3,4-tetrahydro-1,5-naphthyridine
  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：

  4-(2-phenylimidazol-1-yl)butanoic acid 在 氯化亚砜 、 triisopropylbenzene 、 ammonium acetate 、 肼 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 16.5h， 生成 6,7-dimethyl-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

• Dienophilicity of Imidazole in Inverse Electron Demand Diels-Alder Reactions; Intramolecular Reactions with 1,2,4-Triazines.
  作者：Christopher E. Neipp、Peter B. Ranslow、Zhaokui Wan、John K. Snyder

  DOI：10.1016/s0040-4039(97)01800-5

  日期：1997.10

  Imidazole and 2-phenylimidazole undergo intramolecular cycloadditions with 1,2,4-triazines tethered between an imidazole nitrogen and the triazinyl C3 position with a trimethylene chain to produce tetrahydro-1,5-naphthyridines following loss of N2 and a nitrile. © 1997 Elsevier Science Ltd.

  咪唑和2-苯基咪唑与1,2,4-三嗪进行分子内环加成，所述1,2,4-三嗪通过三亚甲基链拴在咪唑氮和三嗪基C3位置之间，从而在失去N 2和腈后生成四氢-1,5-萘啶。©1997爱思唯尔科学有限公司。
• Convergent Synthesis of a Complex Oxime Library Using Chemical Domain Shuffling
  作者：Shun Su、Dayle E. Acquilano、Jeevanandam Arumugasamy、Aaron B. Beeler、Erin L. Eastwood、Joshua R. Giguere、Ping Lan、Xiaoguang Lei、Geanna K. Min、Adam R. Yeager、Ya Zhou、James S. Panek、John K. Snyder、Scott E. Schaus、John A. Porco

  DOI：10.1021/ol051023r

  日期：2005.6.1

  yThe synthesis of a complex hybrid oxime library is reported utilizing convergent ligation of alkoxyamine and carbonyl monomers via "chemical domain shuffling". Initial biological screening of the library against human small cell lung carcinoma (A549) cells led to the identification of a novel hybrid dimer in contrast to the corresponding monomeric compounds which were found to be inactive.
• Intramolecular Inverse-Electron-Demand Diels−Alder Reactions of Imidazoles with 1,2,4-Triazines:  A New Route to 1,2,3,4-Tetrahydro-1,5-naphthyridines and Related Heterocycles
  作者：Brian R. Lahue、Sie-Mun Lo、Zhao-Kui Wan、Grace H. C. Woo、John K. Snyder

  DOI：10.1021/jo040193z

  日期：2004.10.1

  The intramolecular inverse-electron-demand Diels−Alder reaction between imidazoles and 1,2,4-triazines linked by a trimethylene tether from the imidazole N1 position to the triazine C3 proceed in excellent yields to produce 1,2,3,4-tetrahydro-1,5-naphthyridines. The reaction proceeds by a cycloaddition with subsequent loss of nitrogen, followed by a presumed stepwise loss of a nitrile. The analogous

  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。
• 1,2,3,4-Tetrahydro-1,5-naphthyridines and related heterocyclic scaffolds: exploration of suitable chemistry for library development
  作者：Grace H.C. Woo、Aaron B. Beeler、John K. Snyder

  DOI：10.1016/j.tet.2007.04.003

  日期：2007.6

  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.