Diospyrin-dimethylether | 14864-63-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Diospyrin-dimethylether
• 英文别名: 5-Methoxy-6-(8-methoxy-6-methyl-1,4-dioxonaphthalen-2-yl)-7-methylnaphthalene-1,4-dione
• CAS: 14864-63-2
• 化学式: C₂₄H₁₈O₆
• 分子量: 402.403
• InChiKey: DKVRCJZTQSGKQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Diospyrin-dimethylether 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以71%的产率得到Diospyrin, 1.1'.4.4'-Tetraoxo-7.7'-dimethyl-5.5'-dihydroxy-1.1'.4.4'-tetrahydro-binaphthyl-(2.6' oder 3.6')
  参考文献：
  名称：

  Total Synthesis of the Antitumor–Antitubercular 2,6′-Bijuglone Natural Product Diospyrin and Its 3,6′-Isomer

  摘要：

  The 2,6'-bijuglone natural product diospyrin and its unnatural 3,6'-isomer idospyrin have been synthesized in seven steps each from N,N-diethylsenecioamide in overall yields of 12% and 13%, respectively. The syntheses diverge from ramentaceone (7-methyljuglone) and include a key Suzuki-Miyaura cross-coupling. Diospyrin, idospyrin, and several synthetic precursors exhibit potent and selective cytotoxicity to the murine myeloma NS-1 cell line over neonatal foreskin cells.

  DOI：

  10.1021/acs.jnatprod.0c00800
• 作为产物：
  描述：

  3-(hydroxymethyl)-5,8-dimethoxynaphthalen-1-ol 在 potassium phosphate 、 正丁基锂 、 ammonium cerium (IV) nitrate 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 pyridinium hydrobromide perbromide 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 97.66h， 生成 Diospyrin-dimethylether
  参考文献：
  名称：

  Total Synthesis of the Antitumor–Antitubercular 2,6′-Bijuglone Natural Product Diospyrin and Its 3,6′-Isomer

  摘要：

  The 2,6'-bijuglone natural product diospyrin and its unnatural 3,6'-isomer idospyrin have been synthesized in seven steps each from N,N-diethylsenecioamide in overall yields of 12% and 13%, respectively. The syntheses diverge from ramentaceone (7-methyljuglone) and include a key Suzuki-Miyaura cross-coupling. Diospyrin, idospyrin, and several synthetic precursors exhibit potent and selective cytotoxicity to the murine myeloma NS-1 cell line over neonatal foreskin cells.

  DOI：

  10.1021/acs.jnatprod.0c00800