methyl 6-hydroxy-8-methoxy-3-methyl-1,7,12-trioxo-1,2,3,4,7,12-hexahydrobenz[a]anthracene-10-carboxylate | 1407804-37-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 角环素
• 英文名称: methyl 6-hydroxy-8-methoxy-3-methyl-1,7,12-trioxo-1,2,3,4,7,12-hexahydrobenz[a]anthracene-10-carboxylate
• 英文别名: methyl 6-hydroxy-8-methoxy-3-methyl-1,7,12-trioxo-3,4-dihydro-2H-benzo[a]anthracene-10-carboxylate
• CAS: 1407804-37-8
• 化学式: C₂₂H₁₈O₇
• 分子量: 394.381
• InChiKey: JJNNTXMPYXKVAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 6-hydroxy-8-methoxy-3-methyl-1,7,12-trioxo-1,2,3,4,7,12-hexahydrobenz[a]anthracene-10-carboxylate 在 盐酸 、 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 丙酮 为溶剂， 生成 Methyl 2-chloro-1,6,8-trimethoxy-3-methyl-7,12-dioxobenzo[a]anthracene-10-carboxylate
  参考文献：
  名称：

  Total Synthesis of Chlorocyclinone A, a PPAR-γ Antagonist

  摘要：

  The first total synthesis of chlorocyclinone A (1) is regioselectively completed in 28 steps. The key steps are Pd-catalyzed methoxycarbonylation, unprecedented Hauser annulation, Krohn photo-oxidation, and regioselective gem-dichlorination.

  DOI：

  10.1021/jo301712b
• 作为产物：
  描述：

  methyl 6-hydroxy-8-methoxy-3-methyl-7,12-dioxo-1,2,3,4,7,12-hexahydrobenz[a]anthracene-10-carboxylate 在 air 作用下， 以 氯仿 为溶剂， 反应 6.0h， 以100%的产率得到methyl 6-hydroxy-8-methoxy-3-methyl-1,7,12-trioxo-1,2,3,4,7,12-hexahydrobenz[a]anthracene-10-carboxylate
  参考文献：
  名称：

  Total Synthesis of Chlorocyclinone A, a PPAR-γ Antagonist

  摘要：

  The first total synthesis of chlorocyclinone A (1) is regioselectively completed in 28 steps. The key steps are Pd-catalyzed methoxycarbonylation, unprecedented Hauser annulation, Krohn photo-oxidation, and regioselective gem-dichlorination.

  DOI：

  10.1021/jo301712b

文献信息

• Total Synthesis of Chlorocyclinone A, a PPAR-γ Antagonist
  作者：Raju Karmakar、Dipakranjan Mal

  DOI：10.1021/jo301712b

  日期：2012.11.16

  The first total synthesis of chlorocyclinone A (1) is regioselectively completed in 28 steps. The key steps are Pd-catalyzed methoxycarbonylation, unprecedented Hauser annulation, Krohn photo-oxidation, and regioselective gem-dichlorination.