Diospyrin, 1.1'.4.4'-Tetraoxo-7.7'-dimethyl-5.5'-dihydroxy-1.1'.4.4'-tetrahydro-binaphthyl-(2.6' oder 3.6') | 14749-91-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Diospyrin, 1.1'.4.4'-Tetraoxo-7.7'-dimethyl-5.5'-dihydroxy-1.1'.4.4'-tetrahydro-binaphthyl-(2.6' oder 3.6')
• 英文别名: 5-Hydroxy-6-(8-hydroxy-6-methyl-1,4-dioxonaphthalen-2-yl)-7-methylnaphthalene-1,4-dione
• CAS: 14749-91-8
• 化学式: C₂₂H₁₄O₆
• 分子量: 374.35
• InChiKey: DDCXOXHWSFIOKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Diospyrin, 1.1'.4.4'-Tetraoxo-7.7'-dimethyl-5.5'-dihydroxy-1.1'.4.4'-tetrahydro-binaphthyl-(2.6' oder 3.6') 生成 diosquinone
  参考文献：
  名称：

  SANKARAM, A. V.;REDDY, V. V. NARAYANA;SHOOLERY, JAMES N., INDIAN J. CHEM., 26,(1987) N 1, 41-46

  摘要：

  DOI：
• 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 aluminum (III) chloride 、 potassium phosphate 、 lithium aluminium tetrahydride 、 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 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 128.66h， 生成 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

文献信息

• 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.
• SANKARAM, A. V.;REDDY, V. V. NARAYANA;SHOOLERY, JAMES N., INDIAN J. CHEM., 26,(1987) N 1, 41-46
  作者：SANKARAM, A. V.、REDDY, V. V. NARAYANA、SHOOLERY, JAMES N.

  DOI：——

  日期：——