3-cloro-4-cyano-10-(1H-indol-3-yl)-5,10-dihydrobenzo[b][1,6]naphthyridine | 655240-82-7

• 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: 3-cloro-4-cyano-10-(1H-indol-3-yl)-5,10-dihydrobenzo[b][1,6]naphthyridine
• 英文别名: 3-chloro-10-(1H-indol-3-yl)-5,10-dihydrobenzo[b][1,6]naphthyridine-4-carbonitrile
• CAS: 655240-82-7
• 化学式: C₂₁H₁₃ClN₄
• 分子量: 356.814
• InChiKey: YVEWMUOLYRUHRU-UHFFFAOYSA-N

物化性质

• 熔点：
  251-251.5 °C(Solv: isopropanol (67-63-0))
• 沸点：
  574.5±50.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  64.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-cloro-4-cyano-10-(1H-indol-3-yl)-5,10-dihydrobenzo[b][1,6]naphthyridine 在 potassium hexacyanoferrate(III) 作用下， 以 水 、 异丙醇 为溶剂， 反应 60.0h， 以44%的产率得到3-chloro-4-cyano-10-(1H-indol-3-yl)benzo[b][1,6]naphthyridine
  参考文献：
  名称：

  摘要：

  Two routes to consecutive functionalization of 3-chloro-4-cyanobenzo[b][1,6]naphthyridine (1a) at positions 3 and 10 were developed. Oxidation of compound la with m-chloro-perbenzoic acid in acetone leads to 3-chloro-4-cyano-10-oxobenzo[b][1,6]naphthyridine, while in acetic acid, the reactiongives 3-chloro-4-cyano-10-(3-chlorobenzoyloxy)-5-hydroxy-5,10-dihydrobenzo[b][1,6]naphthyridine. The reactions of la with some C-nucleophiles give sigma-adducts at position 10. The reactions of N,N-dimethylamide acetals with chloride la leads to 4-cyano-3-dimethylaminobenzo[b][1,6]naphthyridine.

  DOI：

  10.1023/a:1024725811506
• 作为产物：
  描述：

  吲哚 、 3-chloro-4-cyanobenzo<1,6>naphthyridine 以 异丙醇 为溶剂， 反应 0.75h， 以87%的产率得到3-cloro-4-cyano-10-(1H-indol-3-yl)-5,10-dihydrobenzo[b][1,6]naphthyridine
  参考文献：
  名称：

  摘要：

  Two routes to consecutive functionalization of 3-chloro-4-cyanobenzo[b][1,6]naphthyridine (1a) at positions 3 and 10 were developed. Oxidation of compound la with m-chloro-perbenzoic acid in acetone leads to 3-chloro-4-cyano-10-oxobenzo[b][1,6]naphthyridine, while in acetic acid, the reactiongives 3-chloro-4-cyano-10-(3-chlorobenzoyloxy)-5-hydroxy-5,10-dihydrobenzo[b][1,6]naphthyridine. The reactions of la with some C-nucleophiles give sigma-adducts at position 10. The reactions of N,N-dimethylamide acetals with chloride la leads to 4-cyano-3-dimethylaminobenzo[b][1,6]naphthyridine.

  DOI：

  10.1023/a:1024725811506

文献信息

• ——
  作者：A. S. Ivanov、N. Z. Tugusheva、L. M. Alekseeva、V. G. Granik

  DOI：10.1023/a:1024725811506

  日期：——

  Two routes to consecutive functionalization of 3-chloro-4-cyanobenzo[b][1,6]naphthyridine (1a) at positions 3 and 10 were developed. Oxidation of compound la with m-chloro-perbenzoic acid in acetone leads to 3-chloro-4-cyano-10-oxobenzo[b][1,6]naphthyridine, while in acetic acid, the reactiongives 3-chloro-4-cyano-10-(3-chlorobenzoyloxy)-5-hydroxy-5,10-dihydrobenzo[b][1,6]naphthyridine. The reactions of la with some C-nucleophiles give sigma-adducts at position 10. The reactions of N,N-dimethylamide acetals with chloride la leads to 4-cyano-3-dimethylaminobenzo[b][1,6]naphthyridine.