2-bromo-3-[4-(2-methyl-[1,3]dioxolan-2-yl)-3-oxobutyl]-[1,4]naphthoquinone | 203377-37-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-bromo-3-[4-(2-methyl-[1,3]dioxolan-2-yl)-3-oxobutyl]-[1,4]naphthoquinone
• 英文别名: 2-Bromo-3-[4-(2-methyl-1,3-dioxolan-2-yl)-3-oxobutyl]naphthalene-1,4-dione
• CAS: 203377-37-1
• 化学式: C₁₈H₁₇BrO₅
• 分子量: 393.234
• InChiKey: ALQLCJSADYXRLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-bromo-3-[4-(2-methyl-[1,3]dioxolan-2-yl)-3-oxobutyl]-[1,4]naphthoquinone 在 palladium on activated charcoal 硫酸 、 氢气 、 silica gel 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 calcium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 2-(3,5-dioxohexyl)-[1,4]naphthoquinone
  参考文献：
  名称：

  Total synthesis of angucyclines. 9. An Alternative Biomimetic-Type Synthesis of 8-Deoxytetrangomycin

  摘要：

  Base-catalyzed cyclization of the naphthoquinone 5 afforded the 1,2-dihydroanthraquinone 6a. The bisallcylation products 9 and 10 were obtained by Stille-type chain elongation of the corresponding triflate 6b with the stannanes 7 or 8. The dihydroanthraquinone 9 is a potential precursor for the SS-228 Y-type angucyclinones, where as the diketone 10 can be converted to 8-deoxytetrangomycin (11).

  DOI：

  10.1002/prac.19983400211
• 作为产物：
  描述：

  2-(3-Bromo-1,4-dioxo-1,4-dihydro-naphthalen-2-ylmethyl)-4-(2-methyl-[1,3]dioxolan-2-yl)-3-oxo-butyric acid methyl ester 在 三丁基氧化锡 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以75%的产率得到2-bromo-3-[4-(2-methyl-[1,3]dioxolan-2-yl)-3-oxobutyl]-[1,4]naphthoquinone
  参考文献：
  名称：

  Total synthesis of angucyclines. 9. An Alternative Biomimetic-Type Synthesis of 8-Deoxytetrangomycin

  摘要：

  Base-catalyzed cyclization of the naphthoquinone 5 afforded the 1,2-dihydroanthraquinone 6a. The bisallcylation products 9 and 10 were obtained by Stille-type chain elongation of the corresponding triflate 6b with the stannanes 7 or 8. The dihydroanthraquinone 9 is a potential precursor for the SS-228 Y-type angucyclinones, where as the diketone 10 can be converted to 8-deoxytetrangomycin (11).

  DOI：

  10.1002/prac.19983400211

文献信息

• Total synthesis of angucyclines. 9. An Alternative Biomimetic-Type Synthesis of 8-Deoxytetrangomycin
  作者：Karsten Krohn、Nasir Hayat

  DOI：10.1002/prac.19983400211

  日期：——

  Base-catalyzed cyclization of the naphthoquinone 5 afforded the 1,2-dihydroanthraquinone 6a. The bisallcylation products 9 and 10 were obtained by Stille-type chain elongation of the corresponding triflate 6b with the stannanes 7 or 8. The dihydroanthraquinone 9 is a potential precursor for the SS-228 Y-type angucyclinones, where as the diketone 10 can be converted to 8-deoxytetrangomycin (11).