4-[1-羟基-2-萘基]-1,2-萘醌 | 121732-90-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 4-[1-羟基-2-萘基]-1,2-萘醌
• 英文名称: 4-<1-hydroxy-2-naphthyl>-1,2-naphthoquinone
• 英文别名: 1'-hydroxy-[1,2'-binaphthalene]-3,4-dione；4-(1-hydroxynaphthalen-2-yl)naphthalene-1,2-dione
• CAS: 121732-90-9
• 化学式: C₂₀H₁₂O₃
• 分子量: 300.313
• InChiKey: DHISWCBEICHHHX-UHFFFAOYSA-N

物化性质

• 熔点：
  223 °C
• 沸点：
  520.1±50.0 °C(Predicted)
• 密度：
  1.382±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-二氨基丙酸 、 4-[1-羟基-2-萘基]-1,2-萘醌 以 甲醇 为溶剂， 反应 5.0h， 以68%的产率得到6-(1-hydroxynaphthalen-2-yl) benzo[f]quinoxaline-2-carboxylic acid
  参考文献：
  名称：

  A New Class of Phenazines with Activity against a Chloroquine Resistant Plasmodium falciparum Strain and Antimicrobial Activity

  摘要：

  New phenazines were synthesized by oxygenation of 1- and 2-naphthol with transition metal peroxo complexes and in situ reaction with 1,2-diamines. The title compounds were evaluated for in vitro antimalarial activity against Plasmodium falciparum and chloroquine-resistant strains. Phenazines 12, 27, and 28 were most prominent in growth inhibition. In vivo protection against cerebral malaria was observed with the phenazines 11, 12, 20, and 27, whereas partial protection was provided by 19.

  DOI：

  10.1021/jm200302d
• 作为产物：
  描述：

  萘酚 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以9%的产率得到1,2-萘醌
  参考文献：
  名称：

  A New Class of Phenazines with Activity against a Chloroquine Resistant Plasmodium falciparum Strain and Antimicrobial Activity

  摘要：

  New phenazines were synthesized by oxygenation of 1- and 2-naphthol with transition metal peroxo complexes and in situ reaction with 1,2-diamines. The title compounds were evaluated for in vitro antimalarial activity against Plasmodium falciparum and chloroquine-resistant strains. Phenazines 12, 27, and 28 were most prominent in growth inhibition. In vivo protection against cerebral malaria was observed with the phenazines 11, 12, 20, and 27, whereas partial protection was provided by 19.

  DOI：

  10.1021/jm200302d

文献信息

• Hypoiodite-catalysed oxidative homocoupling of arenols and tandem oxidation/cross-coupling of hydroquinones with arenes
  作者：Muhammet Uyanik、Dai Nagata、Kazuaki Ishihara

  DOI：10.1039/d1cc05171g

  日期：——

  We report the hypoiodite-catalyzed oxidative C–C homocoupling of arenols to biarenols or biquinones using aqueous hydrogen peroxide as an oxidant. In addition, by combining hypoiodite catalysis and lipophilic Lewis acid-assisted Brønsted acid catalysis under aqueous conditions, we achieved a tandem oxidation/cross-coupling reaction of hydroquinones with electron-rich arenes. These results highlight

  我们报告了使用过氧化氢水溶液作为氧化剂的次碘酸盐催化氧化 C-C 同偶联的壬醇与双烯醇或双醌。此外，通过在水性条件下结合次碘酸盐催化和亲脂性路易斯酸辅助布朗斯台德酸催化，我们实现了对苯二酚与富电子芳烃的串联氧化/交叉偶联反应。这些结果突出了次碘酸盐/酸共催化在氧化偶联反应中的应用范围。
• Krohn, Karsten; Rieger, Hagen; Khanbabaee, Karamali, Chemische Berichte, 1989, vol. 122, p. 2323 - 2330
  作者：Krohn, Karsten、Rieger, Hagen、Khanbabaee, Karamali

  DOI：——

  日期：——
• A New Class of Phenazines with Activity against a Chloroquine Resistant <i>Plasmodium falciparum</i> Strain and Antimicrobial Activity
  作者：Hidayat Hussain、Sabine Specht、Salem R. Sarite、Michael Saeftel、Achim Hoerauf、Barbara Schulz、Karsten Krohn

  DOI：10.1021/jm200302d

  日期：2011.7.14

  New phenazines were synthesized by oxygenation of 1- and 2-naphthol with transition metal peroxo complexes and in situ reaction with 1,2-diamines. The title compounds were evaluated for in vitro antimalarial activity against Plasmodium falciparum and chloroquine-resistant strains. Phenazines 12, 27, and 28 were most prominent in growth inhibition. In vivo protection against cerebral malaria was observed with the phenazines 11, 12, 20, and 27, whereas partial protection was provided by 19.