4-Demethoxy-4-<2'-(methoxycarbonyl)ethenyl>-13-dioxolanyldaunomycinone | 135340-34-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: 4-Demethoxy-4-<2'-(methoxycarbonyl)ethenyl>-13-dioxolanyldaunomycinone
• 英文别名: methyl (E)-3-[(8S,10S)-6,8,10,11-tetrahydroxy-8-(2-methyl-1,3-dioxolan-2-yl)-5,12-dioxo-9,10-dihydro-7H-tetracen-1-yl]prop-2-enoate
• CAS: 135340-34-0
• 化学式: C₂₆H₂₄O₁₀
• 分子量: 496.471
• InChiKey: ZONGWQQMZYXSKZ-RCBOMVNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  160
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  4-Demethyl-4-(trifluoromethanesulfonyl)-13-dioxolanyldaunomycinone 、 丙烯酸甲酯（MA） 在 Pd(OAc)2-1,1'-bis(diphenylphosphino)ferrocene lithium acetate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以62%的产率得到4-Demethoxy-4-<2'-(methoxycarbonyl)ethenyl>-13-dioxolanyldaunomycinone
  参考文献：
  名称：

  Heck reaction on anthraquinone derivatives: ligand, solvent and salt effects

  摘要：

  The palladium-catalyzed Heck reaction of trifluoromethanesulfonates of anthraquinoid systems is described. The outcome of the reaction between methyl acrylate 4 and 1-(9,10-anthraquinoyl)trifluoromethanesulfonate 7 (reduction versus arylation) is strongly correlated to the choice of ligand, solvent, and added salt. The results are explained in terms of different coordination-insertion pathways as a function of the reaction conditions. Best conditions have been transferred to the synthesis of novel anthracyclinone, 4-demethoxy-4-(2'-methoxycarbonyl)ethenyl-13-dioxolanyldaunomycinone 5.

  DOI：

  10.1021/jo00020a020

文献信息

• Heck reaction on anthraquinone derivatives: ligand, solvent and salt effects
  作者：Walter Cabri、Ilaria Candiani、Silvia DeBernardinis、Franco Francalanci、Sergio Penco、Roberto Santo

  DOI：10.1021/jo00020a020

  日期：1991.9

  The palladium-catalyzed Heck reaction of trifluoromethanesulfonates of anthraquinoid systems is described. The outcome of the reaction between methyl acrylate 4 and 1-(9,10-anthraquinoyl)trifluoromethanesulfonate 7 (reduction versus arylation) is strongly correlated to the choice of ligand, solvent, and added salt. The results are explained in terms of different coordination-insertion pathways as a function of the reaction conditions. Best conditions have been transferred to the synthesis of novel anthracyclinone, 4-demethoxy-4-(2'-methoxycarbonyl)ethenyl-13-dioxolanyldaunomycinone 5.