6-Hydroxy-4,9-dimethoxy-9-methyl-7,8,9,10-tetrahydronaphthacen-5,12-dione | 224447-26-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 6-Hydroxy-4,9-dimethoxy-9-methyl-7,8,9,10-tetrahydronaphthacen-5,12-dione
• CAS: 224447-26-1
• 化学式: C₂₁H₂₂O₅
• 分子量: 354.403
• InChiKey: LMQPAKVNZOJMTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6-Hydroxy-4,9-dimethoxy-9-methyl-7,8,9,10-tetrahydronaphthacen-5,12-dione 在 氧气 作用下， 反应 24.0h， 生成 11-Hydroxy-1,8-dimethoxy-8-methyl-7,8,9,10-tetrahydro-naphthacene-5,12-dione
  参考文献：
  名称：

  Studies Toward the Synthesis of Menogaril: Synthesis of A-Ring Precursors and Their Conversion to the Tetracyclic Core via the Benzannulation Reaction

  摘要：

  报告中介绍了一种合成 menogaril 的模型研究，其中涉及一种 Fischer 碳烯络合物与含有 menogaril 四环核心 A 环的炔烃的苯并反应。报告还介绍了这种炔烃的甲氧基和苄氧基衍生物的合成，以及甲氧基衍生物与邻甲氧基苯基碳烯络合物的反应，生成了含有 menogaril 核心四个环中的三个环的三环萘酚。通过分子内弗里德尔-卡夫斯环化反应，完成了模型研究并合成了 menogaril 的四环蒽酮核心。

  DOI：

  10.1055/s-1999-3402
• 作为产物：
  描述：

  在 silver(II) oxide 、 水 、 硝酸 、 四氯化锡 作用下， 以 丙酮 、 苯 为溶剂， 反应 0.33h， 生成 6-Hydroxy-4,9-dimethoxy-9-methyl-7,8,9,10-tetrahydronaphthacen-5,12-dione
  参考文献：
  名称：

  Studies Toward the Synthesis of Menogaril: Synthesis of A-Ring Precursors and Their Conversion to the Tetracyclic Core via the Benzannulation Reaction

  摘要：

  报告中介绍了一种合成 menogaril 的模型研究，其中涉及一种 Fischer 碳烯络合物与含有 menogaril 四环核心 A 环的炔烃的苯并反应。报告还介绍了这种炔烃的甲氧基和苄氧基衍生物的合成，以及甲氧基衍生物与邻甲氧基苯基碳烯络合物的反应，生成了含有 menogaril 核心四个环中的三个环的三环萘酚。通过分子内弗里德尔-卡夫斯环化反应，完成了模型研究并合成了 menogaril 的四环蒽酮核心。

  DOI：

  10.1055/s-1999-3402

文献信息

• Synthesis of the Tetracyclic Carbon Core of Menogaril Utilizing the Benzannulation Reaction of a Fischer Carbene Complex and an Alkyne
  作者：Jing Su、William D. Wulff、Richard G. Ball

  DOI：10.1021/jo981481w

  日期：1998.11.1

  The synthesis of the 2-bromoanthracyclinone 3 containing the tetracyclic core of menogaril is achieved with a strategy that is formulated around the benzannulation reaction of a Fischer carbene complex and an alkyne. This benzannulation requires a 2,5-dimethoxyphenyl carbene complex that bears an additional functional group at the 4-position that is the nascent 2-bromo substituent in 3. The evaluation of 4-bromo- and 4-trimethysilyl-substituted complexes with 1-pentyne revealed that the benzannulation was more efficient with the silyl complex. The synthesis of 3 is achieved with methoxy and acetoxy substituents at the C-9 position, which begins with the methoxy- and benzyloxy-substituted alkynes 14 and 30 that contain the A ring of the menogaril core. The closure of the last ring is accomplished by a Friedel-Crafts reaction on an in situ generated acid chloride. Adjustment of the oxidation states of the B and C rings failed according to procedures that had been developed in model studies. This was accomplished in an unexpected fashion with novel bromination reactions that occurred at a benzylic position with the C-9 methoxyl derivative and alpha to a ketone in the C-9 acetoxy derivative.