6-methyl-1-phenyl-1,2,3,4,5,6,7,8-octahydro-1,6-naphthyridine | 215713-90-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-methyl-1-phenyl-1,2,3,4,5,6,7,8-octahydro-1,6-naphthyridine
• 英文别名: 1-phenyl-6-methyl-1,2,3,4,5,6,7,8-octahydro-1,6-naphthiridine；6-Methyl-1-phenyl-2,3,4,5,7,8-hexahydro-1,6-naphthyridine
• CAS: 215713-90-9
• 化学式: C₁₅H₂₀N₂
• 分子量: 228.337
• InChiKey: OHEAQGKYEJFVAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-methyl-1-phenyl-1,2,3,4,5,6,7,8-octahydro-1,6-naphthyridine 在 甲酸 作用下， 反应 8.0h， 以36%的产率得到trans-6-methyl-1-phenyldecahydro-1,6-naphthyridine
  参考文献：
  名称：

  cis-and trans-decahydro-1,6-naphthyridines. Stereoselective synthesis and stereochemistry

  摘要：

  New 1,6-disubstituted trans-decahydro-1,6-naphthyridines were synthesized by stereoselective nucleophilic addition of hydride and cyanide ions to 1,2,3,4,5,6,7,8-octabydro-1,6-naphthyridines, and their predominant conformations were determined. Some trans-decahydro-1,6-naphthyridine derivatives were found to exhibit anti-HIV activity.

  DOI：

  10.1134/s1070428006060194
• 作为产物：
  描述：

  1-甲基-N-苯基哌啶-4-亚胺 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.0h， 生成 6-methyl-1-phenyl-1,2,3,4,5,6,7,8-octahydro-1,6-naphthyridine
  参考文献：
  名称：

  一种简单，便捷的途径合成1,2,3,4,5,6,7,8-八氢-1,6-萘啶

  摘要：

  已经开发了一种简单方便的合成方法，用于新系列的1,2,3,4,5,6,7,8-八氢-1,6-萘啶1a-j。这是通过结合金属化的4-哌啶亚胺烷基化和分子内环化的一锅法实现的。

  DOI：

  10.1016/s0040-4039(98)01662-1

文献信息

• Synthesis and conformational study of 1,2,3,4,5,6,7,8-octahydro-1,6-naphthiridines
  作者：T. V. Esipova、A. A. Borisenko、P. B. Terent’ev、G. V. Grishina、R. Herzshuh

  DOI：10.1134/s1070428006050162

  日期：2006.5

  A new class of endocyclic enamines, 1,6-disubstituted 1,2,3,4,5,6,7,8-octahydro-1,6-naphthiridines, was synthesized from 4-piperidone imines by successive subjecting the latter to lithiation with lithium diethylamide, to alkylation with 1-bromo-3-chloropropane, and to intramolecular cyclization. All stages were carried out as a unique process without isolation of the intermediate compounds. A thorough optimization of the process conditions, workup, and product storage was carried out. The conformational study of 1,6-disubstituted 1,2,3,4,5,6,7,8-octahydro-1,6-naphthiridines was performed.