methyl (7S,11S)-10-10-dimethyl-8-oxo-7-[(1S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidenemethyl]-7,8,9,10,11,12-hexahydrobenzo[c]acridine-11-carboxylate | 1251735-83-7

• 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
• 英文名称: methyl (7S,11S)-10-10-dimethyl-8-oxo-7-[(1S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidenemethyl]-7,8,9,10,11,12-hexahydrobenzo[c]acridine-11-carboxylate
• CAS: 1251735-83-7
• 化学式: C₃₂H₃₇NO₃
• 分子量: 483.651
• InChiKey: XFVPJGMQUIDZEX-DZIOPZPQSA-N

物化性质

• 沸点：
  591.5±50.0 °C(predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.16
• 重原子数：
  36.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2,2-二甲基-4,6-二氧环己烷-1-羧酸甲酯 、 1-萘胺 、 [(1S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene]acetaldehyde 以 乙醇 为溶剂， 生成 methyl (7R,11R)-10,10-dimethyl-8-oxo-7-[(1S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidenemethyl]-7,8,9,10,11,12-hexahydrobenzo[c]acridine-11-carboxylate 、 methyl (7R,11S)-10,10-dimethyl-8-oxo-7-[(1S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidenemethyl]-7,8,9,10,11,12-hexahydrobenzo[c]acridine-11-carboxylate 、 methyl (7S,11R)-10,10-dimethyl-8-oxo-7-[(1S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidenemethyl]-7,8,9,10,11,12-hexahydrobenzo[c]acridine-11-carboxylate 、 methyl (7S,11S)-10-10-dimethyl-8-oxo-7-[(1S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidenemethyl]-7,8,9,10,11,12-hexahydrobenzo[c]acridine-11-carboxylate
  参考文献：
  名称：

  Synthesis of chiral benzoacridinone derivatives by three-component condensation of [(1S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene]acetaldehyde with naphthalen-1-amine and cyclic β-diketones

  摘要：

  Three-component condensation of [(1S,4S)-1,7,7-trimethylbicyclo[2.2.1] hept-2-ylidene] acetaldehyde with naphthalen-1-amine and cyclic beta-diketones gave 7-[(1S,4S)-1,7,7-trimethylbicyclo[2.2.1] hept-2-ylidenemethyl]-7,8,9,10,11,12-hexahydro-7H-benzo[c] acridin-8-one derivatives possessing three or more asymmetric carbon atoms. Steric factors were found to be responsible for the predominant formation of the (7R)-isomers (R/S approximate to 7 : 5) and orientation of substituents in the cyclohexenone fragment. The same factors determined complete regioselectivity of the reaction with methyl 2,4-dioxocyclohexane-1-carboxylates as dicarbonyl component, which led to exclusive formation of methyl 8-oxobenzoacridine-11-carboxylates. In the reaction of [(1S, 4S)-1,7,7-trimethylbicyclo[2.2.1] hept-2-ylidene] acetaldehyde with naphthalen-1-amine and barbituric acid as dicarbonyl component, the only product was that formed by two-component condensation of barbituric acid with bicyclic aldehyde.

  DOI：

  10.1134/s1070428010080038