9-Oxo-2,3-diphenylfluorene-1,4-dicarboxylic acid | 1149350-05-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9-Oxo-2,3-diphenylfluorene-1,4-dicarboxylic acid
• CAS: 1149350-05-9
• 化学式: C₂₇H₁₆O₅
• 分子量: 420.421
• InChiKey: RBUQRVRXEIQJOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-Oxo-2,3-diphenylfluorene-1,4-dicarboxylic acid 在 硫酸 作用下， 反应 3.0h， 以78%的产率得到9,14,15-Trioxo-14,15-dihydro-9H-diindeno<1,2-a;2',1'-c>fluoren
  参考文献：
  名称：

  Facile Multistep Synthesis of Isotruxene and Isotruxenone

  摘要：

  Three multistep approaches toward facile syntheses of isotruxene (1) and isotruxenone (3) are reported. The ortho-para conjugated backbone in the precursor 4 was constructed by either Co-catalyzed [2 + 2 + 2] cyclotrimerization or the [4 + 2] Diels-Alder reactions. The regioselectivity of the triple intramolecular Friedel-Crafts acylation of 4 plays the key role in determining the overall yield. Compared to the previous one-step method, the current approaches are more efficient in terms of product yield (27-36% vs 4-18%) and purification (i.e., free of column chromatography).

  DOI：

  10.1021/jo900299q
• 作为产物：
  描述：

  1,4-Dimethyl-2,3-diphenyl-fluoren-9-one 在 吡啶 、 potassium permanganate 作用下， 以 水 为溶剂， 反应 20.0h， 以76%的产率得到9-Oxo-2,3-diphenylfluorene-1,4-dicarboxylic acid
  参考文献：
  名称：

  Facile Multistep Synthesis of Isotruxene and Isotruxenone

  摘要：

  Three multistep approaches toward facile syntheses of isotruxene (1) and isotruxenone (3) are reported. The ortho-para conjugated backbone in the precursor 4 was constructed by either Co-catalyzed [2 + 2 + 2] cyclotrimerization or the [4 + 2] Diels-Alder reactions. The regioselectivity of the triple intramolecular Friedel-Crafts acylation of 4 plays the key role in determining the overall yield. Compared to the previous one-step method, the current approaches are more efficient in terms of product yield (27-36% vs 4-18%) and purification (i.e., free of column chromatography).

  DOI：

  10.1021/jo900299q

文献信息

• Facile Multistep Synthesis of Isotruxene and Isotruxenone
  作者：Jye-Shane Yang、Hsin-Hau Huang、Shih-Hsun Lin

  DOI：10.1021/jo900299q

  日期：2009.5.15

  Three multistep approaches toward facile syntheses of isotruxene (1) and isotruxenone (3) are reported. The ortho-para conjugated backbone in the precursor 4 was constructed by either Co-catalyzed [2 + 2 + 2] cyclotrimerization or the [4 + 2] Diels-Alder reactions. The regioselectivity of the triple intramolecular Friedel-Crafts acylation of 4 plays the key role in determining the overall yield. Compared to the previous one-step method, the current approaches are more efficient in terms of product yield (27-36% vs 4-18%) and purification (i.e., free of column chromatography).