[6-(Benzoyloxymethyl)-6,9-dihydroxy-5,10-dioxo-9-tricyclo[6.2.2.02,7]dodeca-3,11-dienyl]methyl benzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [6-(Benzoyloxymethyl)-6,9-dihydroxy-5,10-dioxo-9-tricyclo[6.2.2.02,7]dodeca-3,11-dienyl]methyl benzoate
• 英文别名: [6-(benzoyloxymethyl)-6,9-dihydroxy-5,10-dioxo-9-tricyclo[6.2.2.02,7]dodeca-3,11-dienyl]methyl benzoate
• 化学式: C₂₈H₂₄O₈
• 分子量: 488.494
• InChiKey: XXUFTPBMJHFXJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [6-(Benzoyloxymethyl)-6,9-dihydroxy-5,10-dioxo-9-tricyclo[6.2.2.02,7]dodeca-3,11-dienyl]methyl benzoate 、 茚 以 均三甲苯 为溶剂， 反应 0.25h， 生成 (12-hydroxy-13-oxotetracyclo[9.2.2.0(2,10).0(3,8)]pentadeca-3,5,7,14-tetraen-12-yl)methyl benzoate 、 (12-hydroxy-13-oxotetracyclo[9.2.2.0(2,10).0(3,8)]pentadeca-3,5,7,14-tetraen-12-yl)methyl benzoate
  参考文献：
  名称：

  Microwave-Based Reaction Screening: Tandem Retro-Diels–Alder/Diels–Alder Cycloadditions ofo-Quinol Dimers

  摘要：

  We have accomplished a parallel screen of cycloaddition partners for o-quinols utilizing a plate-based microwave system. Microwave irradiation improves the efficiency of retro-Diels-Alder/Diels-Alder cascades of o-quinol dimers which generally proceed in a diastereoselective fashion. Computational studies indicate that asynchronous transition states are favored in Diels-Alder cycloadditions of o-quinols. Subsequent biological evaluation of a collection of cycloadducts has identified an inhibitor of activator protein-1 (AP-1), an oncogenic transcription factor.

  DOI：

  10.1021/jo201658y

文献信息

• Microwave-Based Reaction Screening: Tandem Retro-Diels–Alder/Diels–Alder Cycloadditions of<i>o</i>-Quinol Dimers
  作者：Suwei Dong、Katharine J. Cahill、Moon-Il Kang、Nancy H. Colburn、Curtis J. Henrich、Jennifer A. Wilson、John A. Beutler、Richard P. Johnson、John A. Porco

  DOI：10.1021/jo201658y

  日期：2011.11.4

  We have accomplished a parallel screen of cycloaddition partners for o-quinols utilizing a plate-based microwave system. Microwave irradiation improves the efficiency of retro-Diels-Alder/Diels-Alder cascades of o-quinol dimers which generally proceed in a diastereoselective fashion. Computational studies indicate that asynchronous transition states are favored in Diels-Alder cycloadditions of o-quinols. Subsequent biological evaluation of a collection of cycloadducts has identified an inhibitor of activator protein-1 (AP-1), an oncogenic transcription factor.