| 856176-27-7

• 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
• CAS: 856176-27-7
• 化学式: C₁₉H₁₈N₂O₃
• 分子量: 322.364
• InChiKey: AQZSDCPDTZASBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  71.45
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  在 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 0.75h， 生成 1,2-dihydro-6-methyl-3-[(4-methylphenyl)amino]-2-oxoquinoline-4-carboxylic acid
  参考文献：
  名称：

  板蓝藻的意外分离物5,7-二氢二苯并[ b，f ] [1,7]萘啶-6,12-二酮的合成

  摘要：

  Abstractmagnified imageThe dye plant Isatis tinctoria yields a number of heterocyclic compounds with interesting anti‐inflammatory and cytotoxic properties, formed mainly in an unknown manner by post‐harvest treatment. A synthesis of the incidently isolated 5,7‐dihydrodibenzo[b,f][1,7]naphthyridine‐6,12‐dione (4a) is presented. Starting from different 1,2‐diarylhydrazines, adducts 11 with acetylenedicarboxylates (=but‐2‐ynedioates) are thermally treated (Scheme). In a Fischer‐type rearrangement, 3‐(arylamino)quinolinecarboxylic acids 9 are obtained, which can be cyclized under Friedel–Crafts conditions to yield a number of analoga 4 of the title compound.

  DOI：

  10.1002/hlca.200800337
• 作为产物：
  描述：

  在 吡啶 作用下， 生成
  参考文献：
  名称：

  板蓝藻的意外分离物5,7-二氢二苯并[ b，f ] [1,7]萘啶-6,12-二酮的合成

  摘要：

  Abstractmagnified imageThe dye plant Isatis tinctoria yields a number of heterocyclic compounds with interesting anti‐inflammatory and cytotoxic properties, formed mainly in an unknown manner by post‐harvest treatment. A synthesis of the incidently isolated 5,7‐dihydrodibenzo[b,f][1,7]naphthyridine‐6,12‐dione (4a) is presented. Starting from different 1,2‐diarylhydrazines, adducts 11 with acetylenedicarboxylates (=but‐2‐ynedioates) are thermally treated (Scheme). In a Fischer‐type rearrangement, 3‐(arylamino)quinolinecarboxylic acids 9 are obtained, which can be cyclized under Friedel–Crafts conditions to yield a number of analoga 4 of the title compound.

  DOI：

  10.1002/hlca.200800337

文献信息

• An Extension of the Diels-Reese Reaction¹
  作者：Ernest H. Huntress、Joseph Bornstein、William M. Hearon

  DOI：10.1021/ja01591a055

  日期：1956.5