6-(p-tolyl)-13b,15-dihydrobenzo[b]benzo[4,5][1,3]oxazino[2,3-f][1,6]naphthyridine | 1443762-23-9

• 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-(p-tolyl)-13b,15-dihydrobenzo[b]benzo[4,5][1,3]oxazino[2,3-f][1,6]naphthyridine
• 英文别名: 13-(4-Methylphenyl)-22-oxa-10,14-diazapentacyclo[12.8.0.02,11.04,9.015,20]docosa-2,4,6,8,10,12,15,17,19-nonaene；13-(4-methylphenyl)-22-oxa-10,14-diazapentacyclo[12.8.0.02,11.04,9.015,20]docosa-2,4,6,8,10,12,15,17,19-nonaene
• CAS: 1443762-23-9
• 化学式: C₂₆H₂₀N₂O
• 分子量: 376.458
• InChiKey: JMYGJHGIPMGIAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  25.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-甲苯基乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 silver nitrate 、 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 生成 6-(p-tolyl)-13b,15-dihydrobenzo[b]benzo[4,5][1,3]oxazino[2,3-f][1,6]naphthyridine
  参考文献：
  名称：

  On Water: Silver-Catalyzed Domino Approach for the Synthesis of Benzoxazine/Oxazine-Fused Isoquinolines and Naphthyridines fromo-Alkynyl Aldehydes

  摘要：

  An operationally simple domino approach for the silver-catalyzed synthesis of oxazine/benzoxazine-fused isoquinolines 5a-q and naphthyridines 6a-v by the reaction of o-alkynyl aldehydes 3a-aa with amines having embedded nucleophiles 4a-d under mild reaction condition in water is described. The reaction shows selective C-N bond formation on the more electrophilic alkynyl carbon resulting in the formation of 6-endo-dig cyclized product. The competitive experiments show the viability of an intramolecular nucleo philic attack over an intermolecular attack of the external nucleophile. This methodology accommodates wide functional group variation, which proves to be useful for structural and biological assessment.

  DOI：

  10.1021/jo4009639

文献信息

• On Water: Silver-Catalyzed Domino Approach for the Synthesis of Benzoxazine/Oxazine-Fused Isoquinolines and Naphthyridines from<i>o</i>-Alkynyl Aldehydes
  作者：Akhilesh K. Verma、Deepak Choudhary、Rakesh K. Saunthwal、Vineeta Rustagi、Monika Patel、Rakesh K. Tiwari

  DOI：10.1021/jo4009639

  日期：2013.7.5

  An operationally simple domino approach for the silver-catalyzed synthesis of oxazine/benzoxazine-fused isoquinolines 5a-q and naphthyridines 6a-v by the reaction of o-alkynyl aldehydes 3a-aa with amines having embedded nucleophiles 4a-d under mild reaction condition in water is described. The reaction shows selective C-N bond formation on the more electrophilic alkynyl carbon resulting in the formation of 6-endo-dig cyclized product. The competitive experiments show the viability of an intramolecular nucleo philic attack over an intermolecular attack of the external nucleophile. This methodology accommodates wide functional group variation, which proves to be useful for structural and biological assessment.