Methyl 9-acetyloxy-3-hydroxy-5,8-dimethoxy-1-methylanthracene-2-carboxylate | 1025933-14-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: Methyl 9-acetyloxy-3-hydroxy-5,8-dimethoxy-1-methylanthracene-2-carboxylate
• CAS: 1025933-14-5
• 化学式: C₂₁H₂₀O₇
• 分子量: 384.386
• InChiKey: HISJSWQWJXJQEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  碘甲烷 、 Methyl 9-acetyloxy-3-hydroxy-5,8-dimethoxy-1-methylanthracene-2-carboxylate 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以120 mg的产率得到9-acetoxy-3,5,8-trimethoxy-1-methyl-anthracene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Extension of the Tandem Conjugate Addition−Dieckmann Condensation:  The Formal Synthesis of Tetracenomycin A₂

  摘要：

  Tandem cuprate addition-Dieckmann condensation is featured in the construction of the polyketide metabolite tetracenomycin A(2) (2). Thus, cyclization substrate 11 was treated with Gilman cuprate Me2CuLi to afford anthracene 12. The phenolic acetate protecting group of 12 ensured its chemoselective oxidation to reveal terminal quinone 13, which intercepts the previously reported synthesis of tetracenomycin A(2) (2).

  DOI：

  10.1021/jo035341k
• 作为产物：
  描述：

  (4-acetoxy-3-iodo-5,8-dimethoxy-naphthalen-2-yl)-acetic acid methyl ester 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 反应 38.17h， 生成 Methyl 9-acetyloxy-3-hydroxy-5,8-dimethoxy-1-methylanthracene-2-carboxylate
  参考文献：
  名称：

  Extension of the Tandem Conjugate Addition−Dieckmann Condensation:  The Formal Synthesis of Tetracenomycin A₂

  摘要：

  Tandem cuprate addition-Dieckmann condensation is featured in the construction of the polyketide metabolite tetracenomycin A(2) (2). Thus, cyclization substrate 11 was treated with Gilman cuprate Me2CuLi to afford anthracene 12. The phenolic acetate protecting group of 12 ensured its chemoselective oxidation to reveal terminal quinone 13, which intercepts the previously reported synthesis of tetracenomycin A(2) (2).

  DOI：

  10.1021/jo035341k

文献信息

• Extension of the Tandem Conjugate Addition−Dieckmann Condensation:  The Formal Synthesis of Tetracenomycin A₂
  作者：Denis V. Kozhinov、Victor Behar

  DOI：10.1021/jo035341k

  日期：2004.2.1

  Tandem cuprate addition-Dieckmann condensation is featured in the construction of the polyketide metabolite tetracenomycin A(2) (2). Thus, cyclization substrate 11 was treated with Gilman cuprate Me2CuLi to afford anthracene 12. The phenolic acetate protecting group of 12 ensured its chemoselective oxidation to reveal terminal quinone 13, which intercepts the previously reported synthesis of tetracenomycin A(2) (2).