methyl (1S,6R)-2,4-dioxo-6-(2,4,6-trimethylphenyl)cyclohexane-1-carboxylate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (1S,6R)-2,4-dioxo-6-(2,4,6-trimethylphenyl)cyclohexane-1-carboxylate
• 化学式: C₁₇H₂₀O₄
• 分子量: 288.343
• InChiKey: HEOFRDHNXXHCFV-BBRMVZONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (1S,6R)-2,4-dioxo-6-(2,4,6-trimethylphenyl)cyclohexane-1-carboxylate 、 2-萘胺 、 [(1S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene]acetaldehyde 以 乙醇 为溶剂， 生成 (8R,9S,12S)-12-(2-bornylidene)methyl-8-methoxycarbonyl-9-(2,4,6-trimethylphenyl)-8,9,10,12-tetrahydro-7H-benzo[a]acridin-11-one 、 (8S,9R,12S)-12-(2-bornylidene)methyl-8-methoxycarbonyl-9-(2,4,6-trimethylphenyl)-8,9,10,12-tetrahydro-7H-benzo[a]acridin-11-one 、 (8R,9S,12R)-12-(2-bornylidene)methyl-8-methoxycarbonyl-9-(2,4,6-trimethylphenyl)-8,9,10,12-tetrahydro-7H-benzo[a]acridin-11-one 、 (8S,9R,12R)-12-(2-bornylidene)methyl-8-methoxycarbonyl-9-(2,4,6-trimethylphenyl)-8,9,10,12-tetrahydro-7H-benzo[a]acridin-11-one
  参考文献：
  名称：

  Synthesis of chiral benzacridone derivatives by three-component condensation

  摘要：

  A three-component condensation of (2-bornylidene)acetaldehyde and 2-naphthylamine with various, in particular, dissymmetrical, cyclic beta-diketones afforded derivatives of 12-(2-bornylidene)methyl-8,9,10,12-tetrahydro-7H-benzo[a]acridin-11-one containing in the structure three and more asymmetrical carbon atoms. Steric factors govern the prevailing formation of (12R)-isomers of benzacridones (R/SH a parts per thousand 7: 5) and the orientation of the substituents of the cyclohexenone fragment. These factors ensure also the regiospecificity of the reaction leading exclusively to the formation of 8,9-disubstituted benzacridones at the use of 4,5-disubstituted cyclohexane-1,3-diones.

  DOI：

  10.1134/s1070428009020067

文献信息

• 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
  作者：S. S. Koval’skaya、N. G. Kozlov、E. A. Dikusar

  DOI：10.1134/s1070428010080038

  日期：2010.8

  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.