7,9-dimethyl-5H-pyrido[1,2,3-cd]perimidin-5-one | 846607-85-0

• 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: 7,9-dimethyl-5H-pyrido[1,2,3-cd]perimidin-5-one
• 英文别名: 12,14-dimethyl-1,3-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-3,5,7,9,11,13,15-heptaen-2-one
• CAS: 846607-85-0
• 化学式: C₁₆H₁₂N₂O
• 分子量: 248.284
• InChiKey: QZGCQLONOYVUFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7,9-dimethyl-5H-pyrido[1,2,3-cd]perimidin-5-one 在 sodium hydroxide 作用下， 反应 0.17h， 以19%的产率得到10-amino-2,4-dimethylbenzo[h]quinoline
  参考文献：
  名称：

  Heterocyclic Analogs of Pleiadiene: LXXIV. peri-Cyclizations in the Perimidine Series. Synthesis of 1,3-Diazapyrene Derivatives

  摘要：

  Reactions of perimidines and perimidin-2-ones with alpha,beta-unsaturated carbonyl compounds gave various 1,3-diazapyrene derivatives. Acylation of 1-methylperimidine, perimidin-2-one, and 1-methylperimidin-2-one with cinnamoyl chloride in the presence of AlBr3 is accompanied by peri-fusion at the 6,7-position and dearylation of the intermediate product. Under analogous conditions, 1,3-dimethyl-2,3-dihydroperimidine gave rise to 6-cinnamoyl-1,3-dimethyl-2,3-dihydroperimidine. Reactions of perimidin-2-ones with 1,3-diphenyl-2-propenone in polyphosphoric acid resulted in peri-fusion at the 6,7-position, and with acetylacetone, at the 1,9-position.

  DOI：

  10.1023/b:rujo.0000044557.95160.e5
• 作为产物：
  描述：

  1H-萘嵌间二氮杂苯-2(3H)-酮 、 乙酰丙酮 在 PPA 作用下， 反应 5.5h， 以87%的产率得到7,9-dimethyl-5H-pyrido[1,2,3-cd]perimidin-5-one
  参考文献：
  名称：

  Heterocyclic Analogs of Pleiadiene: LXXIV. peri-Cyclizations in the Perimidine Series. Synthesis of 1,3-Diazapyrene Derivatives

  摘要：

  Reactions of perimidines and perimidin-2-ones with alpha,beta-unsaturated carbonyl compounds gave various 1,3-diazapyrene derivatives. Acylation of 1-methylperimidine, perimidin-2-one, and 1-methylperimidin-2-one with cinnamoyl chloride in the presence of AlBr3 is accompanied by peri-fusion at the 6,7-position and dearylation of the intermediate product. Under analogous conditions, 1,3-dimethyl-2,3-dihydroperimidine gave rise to 6-cinnamoyl-1,3-dimethyl-2,3-dihydroperimidine. Reactions of perimidin-2-ones with 1,3-diphenyl-2-propenone in polyphosphoric acid resulted in peri-fusion at the 6,7-position, and with acetylacetone, at the 1,9-position.

  DOI：

  10.1023/b:rujo.0000044557.95160.e5