1-(p-tolyl)-6-benzyl-1,2,3,4,5,6,7,8-octahydro-1,6-naphthiridine | 929878-63-7

• 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: 1-(p-tolyl)-6-benzyl-1,2,3,4,5,6,7,8-octahydro-1,6-naphthiridine
• CAS: 929878-63-7
• 化学式: C₂₂H₂₆N₂
• 分子量: 318.462
• InChiKey: WRTDWIAWLVIYDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  6.48
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(p-tolyl)-6-benzyl-1,2,3,4,5,6,7,8-octahydro-1,6-naphthiridine 在 甲酸 作用下， 反应 8.0h， 以7.2%的产率得到cis-6-benzyl-1-(p-tolyl)decahydro-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：

  N-苄基哌啶酮 在 lithium diethylamide 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 2.0h， 生成 1-(p-tolyl)-6-benzyl-1,2,3,4,5,6,7,8-octahydro-1,6-naphthiridine
  参考文献：
  名称：

  Synthesis and conformational study of 1,2,3,4,5,6,7,8-octahydro-1,6-naphthiridines

  摘要：

  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.

  DOI：

  10.1134/s1070428006050162

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.
• cis-and trans-decahydro-1,6-naphthyridines. Stereoselective synthesis and stereochemistry
  作者：T. V. Esipova、A. A. Borisenko、G. V. Grishina

  DOI：10.1134/s1070428006060194

  日期：2006.6

  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.