8,11-dimethoxy-3,4-dihydro-2H-benzo[a]anthracene-1,7,12-trione | 1361013-95-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 角环素
• 英文名称: 8,11-dimethoxy-3,4-dihydro-2H-benzo[a]anthracene-1,7,12-trione
• CAS: 1361013-95-7
• 化学式: C₂₀H₁₆O₅
• 分子量: 336.344
• InChiKey: NXRDEXIDWPPRDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(3-bromo-5,8-dimethoxy-1,4-bis(methoxymethoxy)naphthalen-2-yl)cyclohex-2-en-1-one 在 ammonium cerium (IV) nitrate 、 palladium diacetate 、 silver carbonate 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 2.0h， 生成 8,11-dimethoxy-3,4-dihydro-2H-benzo[a]anthracene-1,7,12-trione
  参考文献：
  名称：

  Cascade assembly of the benz[a]anthraquinone ring system common to the angucycline antibiotics

  摘要：

  A benz[a]anthraquinone ring system, common to a group of angucycline antibiotics, has been prepared by a unique cascade of reactions. The reaction sequence was initiated by a Suzuki-Miyaura cross-coupling between a bromoquinone and vinyl boronic anhydride. The reaction product is proposed to undergo a 6 pi-electron cyclization triggered by reductive activation of the quinone. The reaction process is proposed to be autocatalytic. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.12.126

文献信息

• Cascade assembly of the benz[a]anthraquinone ring system common to the angucycline antibiotics
  作者：Aleksandra Baranczak、Gary A. Sulikowski

  DOI：10.1016/j.tetlet.2011.12.126

  日期：2012.3

  A benz[a]anthraquinone ring system, common to a group of angucycline antibiotics, has been prepared by a unique cascade of reactions. The reaction sequence was initiated by a Suzuki-Miyaura cross-coupling between a bromoquinone and vinyl boronic anhydride. The reaction product is proposed to undergo a 6 pi-electron cyclization triggered by reductive activation of the quinone. The reaction process is proposed to be autocatalytic. (C) 2012 Elsevier Ltd. All rights reserved.