3-chloro-5-phenyl-12H-isoquino[2,3-a]quinazoline | 1134310-29-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 3-chloro-5-phenyl-12H-isoquino[2,3-a]quinazoline
• 英文别名: 3-chloro-5-phenyl-12H-isoquinolino[2,3-a]quinazoline
• CAS: 1134310-29-4
• 化学式: C₂₂H₁₅ClN₂
• 分子量: 342.827
• InChiKey: XZIPUMUHCXORAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  25
• 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：
  15.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-chloro-5-phenyl-12H-isoquino[2,3-a]quinazoline 、 2,4'-二溴苯乙酮 以 乙腈 为溶剂， 以53%的产率得到
  参考文献：
  名称：

  Condensed isoquinolines 31. Reaction of 5-aryl-3-halo-12H-isoquino[2,3-a]quinazolines with electrophilic reagents

  摘要：

  Treatment of 5-aryl-3-halo-12H-isoquino[2,3-a]quinazolines with electrophilic reagents readily forms their oxidation products. Acylation of the 3-chloro-5-phenyl-7,12-dihydroisoquino[2,3-a]quinazolinium perchlorate with Ac(2)O in the presence of pyridine gave the product of electrophilic substitution at the C-7 atom 1-(3-chloro-5-phenyl-12H-isoquino[2,3-a]quinazolin-7-yl)-1-ethanone. By the same route phenacyl bromides react with the anhydro base 1 to give 5-aryl-7-(2-aryl-2-oxoethyl)-3-halo-isoquino[2,3-a]quinazolin-13-ium bromides. These salts readily react with nucleophilic reagents to form the products of addition at the C-12 atom.

  DOI：

  10.1007/s10593-008-0117-2
• 作为产物：
  描述：

  3-chloro-5-phenylisoquino[2,3-a]quinazolin-13-ium perchlorate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以25%的产率得到3-chloro-5-phenyl-12H-isoquino[2,3-a]quinazoline
  参考文献：
  名称：

  Condensed isoquinolines 29. Oxidation reactions of 5-aryl-7,12-dihydroisoquino[2,3-a]quinazolinium salts

  摘要：

  5-Aryl-7,12-dihydroisoquino[2,3-a]quinazolinium perchlorates are readily oxidized by atmospheric oxygen to form the products of oxidative coupling 5,5'-bis(aryl)-3,3'-dihalo[7,7']bi[isoquino-[2,3-a]quinazoline-13,13'-diylium perchlorates. Heating 3-chloro-5-phenyl-7,12-dihydroisoquino-[2,3-a]quinazolinium perchlorate in nitrobenzene gives the 3-chloro-5-phenylisoquino[2,3-a]quinazolin-13-ium perchlorate. The aromatic 5-arylisoquino[2,3-a]quinazoline derivatives obtained react with nucleophilic reagents to form addition products at the C-12 atom.

  DOI：

  10.1007/s10593-008-0049-x