2-(1',4',5'-trimethoxy-7'-methylnaphthalen-6'-yl)-5-methoxy-7-methyl-1,4-naphthoquinone | 273200-97-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1',4',5'-trimethoxy-7'-methylnaphthalen-6'-yl)-5-methoxy-7-methyl-1,4-naphthoquinone
• 英文别名: 1′,5,5′,8′-tetramethoxy-3′,7-dimethyl-[2,2′-binaphthalene]-1,4-dione；GAP-R370；5-Methoxy-7-methyl-2-(1,5,8-trimethoxy-3-methylnaphthalen-2-yl)naphthalene-1,4-dione
• CAS: 273200-97-8
• 化学式: C₂₆H₂₄O₆
• 分子量: 432.473
• InChiKey: YUNVZEWFMYFZAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(1',4',5'-trimethoxy-7'-methylnaphthalen-6'-yl)-5-methoxy-7-methyl-1,4-naphthoquinone 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.83h， 以100%的产率得到diospyrin dimethyl ether
  参考文献：
  名称：

  Synthesis of Diospyrin, a Potential Agent Against Leishmaniasis and Related Parasitic Protozoan Diseases

  摘要：

  The first synthesis of diospyrin [2,6'-bis(5-hydroxy-7-methyl-1,4-naphthoquinone), Ij was achieved by employing Suzuki coupling between 5 and 14 as the key reaction to connect the two 7-methyljuglone units.

  DOI：

  10.1002/1099-0690(200004)2000:7<1313::aid-ejoc1313>3.0.co;2-i
• 作为产物：
  描述：

  4-(乙酰基氧基)-5,8-二甲氧基-2-萘羧酸乙酯 在 potassium phosphate 、 lithium aluminium tetrahydride 、 正丁基锂 、 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 为溶剂， 反应 112.33h， 生成 2-(1',4',5'-trimethoxy-7'-methylnaphthalen-6'-yl)-5-methoxy-7-methyl-1,4-naphthoquinone
  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

文献信息

• Synthesis of Diospyrin, a Potential Agent Against Leishmaniasis and Related Parasitic Protozoan Diseases
  作者：Masao Yoshida、Kenji Mori

  DOI：10.1002/1099-0690(200004)2000:7<1313::aid-ejoc1313>3.0.co;2-i

  日期：2000.4

  The first synthesis of diospyrin [2,6'-bis(5-hydroxy-7-methyl-1,4-naphthoquinone), Ij was achieved by employing Suzuki coupling between 5 and 14 as the key reaction to connect the two 7-methyljuglone units.
• Total Synthesis of the Antitumor–Antitubercular 2,6′-Bijuglone Natural Product Diospyrin and Its 3,6′-Isomer
  作者：Glenn A. Pullella、Daniel Vuong、Ernest Lacey、Matthew J. Piggott

  DOI：10.1021/acs.jnatprod.0c00800

  日期：2020.12.24

  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.