4-methoxy-1,2,3,3a,4,10,10a,10b-octahydro-2-phenyl-1,3,10-trioxoindeno<2,1-e>isoindole | 133446-22-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4-methoxy-1,2,3,3a,4,10,10a,10b-octahydro-2-phenyl-1,3,10-trioxoindeno<2,1-e>isoindole
• 英文别名: 4-methoxy-2-phenyl-3a,4,10a,10b-tetrahydroindeno[2,1-e]isoindole-1,3,10-trione
• CAS: 133446-22-7
• 化学式: C₂₂H₁₇NO₄
• 分子量: 359.381
• InChiKey: SKOYTZDRBFISDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  methyl 2-(3-methoxy-1-propynyl)benzoate 在 rhodium(II) octanoate potassium trimethylsilonate 、 氯甲酸甲酯 作用下， 以 苯 为溶剂， 反应 24.0h， 生成 4-methoxy-1,2,3,3a,4,10,10a,10b-octahydro-2-phenyl-1,3,10-trioxoindeno<2,1-e>isoindole
  参考文献：
  名称：

  Rhodium(II)-catalyzed cyclization reactions of alkynyl-substituted .alpha.-diazo ketones

  摘要：

  Treatment of several omicron-alkynl-substituted alpha-diazoacetophenone derivatives with rhodium (II) carboxylates results in the formation of substituted indenones. The simplest mechanism accounting for the results involves addition of a rhodium-stabilized carbenoid onto the acetylenic pi-bond to generate a vinyl carbenoid directly of possibly a highly strained cyclopropene derivative. The vinyl carbenoid was found to undergo addition to a neighboring alkene tethered on the side chain to give an indenyl-substituted bicyclo[3.1.0]hexane derivative. A number of related systems were examined so as to probe the scope and generality of the process. Treatment of omicron-(6,8-nonadien-1-ynyl)-alpha-diazoacetophenone with rhodium (II) mandelate afforded a cyclopent[g]azulenone derivative. The formation of this compound involves a divinylcyclopropane intermediate that readily undergoes a Cope rearrangement under the reaction conditions. The rhodium-catalyzed reaction of 2-(6-oxo-1-hepty-nyl)-alpha-diazoacetophenone in the presence of N-phenylmaleimide afforded a mixture of two cycloadducts. One of the products can be accounted for in terms of a cyclization of the vinyl carbenoid onto the oxygen atom of the neighboring carbonyl group to give a resonance-stabilized dipole. 1,3-Dipolar cycloaddition of the carbonyl ylide across the activated pi-bond of N-phenylmaleimide affords the observed product. The second cycloadduct is formed by a 1,2-hydrogen shift of the initially produced vinyl carbenoid. The resulting diene undergoes a subsequent Diels-Alder reactions with N-phenylmaleimide.

  DOI：

  10.1021/jo00007a047