1-methyl-6,8-diphenyl-1,3-diazapyren-2-one | 475116-04-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-methyl-6,8-diphenyl-1,3-diazapyren-2-one
• 英文别名: 1-methyl-6,8-diphenyl-1,2-dihydro-1,3-diazapyren-2-one；1-Methyl-6,8-diphenyl-1,2-dihydro-1,3-diaza-pyren-2-one；7-methyl-12,14-diphenyl-5,7-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4,8(16),9,11,13-heptaen-6-one
• CAS: 475116-04-2
• 化学式: C₂₇H₁₈N₂O
• 分子量: 386.453
• InChiKey: DQOWRBKCYCDPPY-UHFFFAOYSA-N

物化性质

• 熔点：
  246-248 °C(Solv: ethanol (64-17-5); ethyl acetate (141-78-6))
• 沸点：
  598.7±60.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 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：

  1-methyl-6,8-diphenyl-1,3-diazapyren-2-one 在 高氯酸 作用下， 以 sodium hydroxide 、 乙腈 为溶剂， 反应 4.67h， 生成 N,N'-dimethyl-9-amino-4,6-diphenyl-1H-phenalen-1-imine
  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：

  6,8-diphenylbenzo[gh]perimidine 在 氢氧化钾 、 potassium hexacyanoferrate(III) 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 5.0h， 生成 1-methyl-6,8-diphenyl-1,3-diazapyren-2-one
  参考文献：
  名称：

  摘要：

  1-Alkyl-1,3-diazapyrenium salts were prepared according to two procedures. Oxidative hydroxylation of these salts afforded 1-alkyl-1,3-diazapyren-2-ones. The spectral characteristics of the resulting compounds are discussed.

  DOI：

  10.1023/a:1015030301555

文献信息

• Heterocyclic Analogs of Pleiadiene: LXXIV. peri-Cyclizations in the Perimidine Series. Synthesis of 1,3-Diazapyrene Derivatives
  作者：I. V. Borovlev、O. P. Demidov、A. V. Aksenov、A. F. Pozharskii

  DOI：10.1023/b:rujo.0000044557.95160.e5

  日期：2004.6

  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.
• ——
  作者：I. V. Borovlev、O. P. Demidov、A. V. Chernyshev、A. F. Pozharskii

  DOI：10.1023/a:1015030301555

  日期：——

  1-Alkyl-1,3-diazapyrenium salts were prepared according to two procedures. Oxidative hydroxylation of these salts afforded 1-alkyl-1,3-diazapyren-2-ones. The spectral characteristics of the resulting compounds are discussed.