1,2,3,4-Tetrahydro-6-hydroxy-8-methoxybenz[α]anthracene-7,12-dione | 255376-39-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 角环素
• 英文名称: 1,2,3,4-Tetrahydro-6-hydroxy-8-methoxybenz[α]anthracene-7,12-dione
• 英文别名: 6-hydroxy-8-methoxy-1,2,3,4-tetrahydrotetraphene-7,12-dione；6-Hydroxy-8-methoxy-1,2,3,4-tetrahydrobenzo[a]anthracene-7,12-dione
• CAS: 255376-39-7
• 化学式: C₁₉H₁₆O₄
• 分子量: 308.334
• InChiKey: WZBICBVEKJGFML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2,3,4-Tetrahydro-6-hydroxy-8-methoxybenz[α]anthracene-7,12-dione 在 air 作用下， 以 氯仿 为溶剂， 以93%的产率得到3,4-Dihydro-6-hydroxy-8-methoxybenz[α]anthracene-1,7,12(2H)-trione
  参考文献：
  名称：

  简洁的全合成巴西硅醌B和C和3-脱氧雷贝霉素

  摘要：

  从普通前体18b的6-7个步骤就完成了巴西iliquinones B和C，2和3和3-deoxyrabelomycin 4a的合成。从四氢萘酮17以区域选择性的方式分五步​​制备关键萘二酮6。氰基邻苯二甲酸酯7c与6的阴离子环化反应很容易以优异的产率提供四环前体5，其在阳光下促进的光氧化作用导致合成标题化合物。

  DOI：

  10.1039/a905667j
• 作为产物：
  描述：

  5,6,7,8-四氢-2-萘酚 在 碘苯二乙酸 、 lithium tert-butoxide 作用下， 以 四氢呋喃 为溶剂， 反应 7.5h， 生成 1,2,3,4-Tetrahydro-6-hydroxy-8-methoxybenz[α]anthracene-7,12-dione
  参考文献：
  名称：

  Selective Oxidative Dearomatization of Angular Tetracyclic Phenols by Controlled Irradiation under Air: Synthesis of an Angucyclinone-Type Double Peroxide with Anticancer Properties

  摘要：

  Angular tetracyclic p-peroxyquinols, p-quinols, and a pentacyclic double peroxide, showing anticancer properties, were synthesized from the corresponding phenols by an environmentally friendly solvent- and wavelength-controlled irradiation under air in the absence of an external photosensitizer.

  DOI：

  10.1021/acs.orglett.8b02515

文献信息

• Selective Oxidative Dearomatization of Angular Tetracyclic Phenols by Controlled Irradiation under Air: Synthesis of an Angucyclinone-Type Double Peroxide with Anticancer Properties
  作者：María J. Cabrera-Afonso、Silvia R. Lucena、Ángeles Juarranz、Antonio Urbano、M. Carmen Carreño

  DOI：10.1021/acs.orglett.8b02515

  日期：2018.10.5

  Angular tetracyclic p-peroxyquinols, p-quinols, and a pentacyclic double peroxide, showing anticancer properties, were synthesized from the corresponding phenols by an environmentally friendly solvent- and wavelength-controlled irradiation under air in the absence of an external photosensitizer.
• A concise total synthesis of brasiliquinones B and C and 3-deoxyrabelomycin
  作者：Dipakranjan Mal、Harendra Nath Roy

  DOI：10.1039/a905667j

  日期：——

  in 6–7 steps from the common precursor 18b. The key naphthalenones 6 were prepared in 5 steps from tetralone 17 in a regioselective manner. Anionic annulation of cyanophthalide 7c with 6 readily provided tetracyclic precursors 5 in excellent yields, sunlight-promoted photooxidation of which led to the synthesis of the title compounds.

  从普通前体18b的6-7个步骤就完成了巴西iliquinones B和C，2和3和3-deoxyrabelomycin 4a的合成。从四氢萘酮17以区域选择性的方式分五步​​制备关键萘二酮6。氰基邻苯二甲酸酯7c与6的阴离子环化反应很容易以优异的产率提供四环前体5，其在阳光下促进的光氧化作用导致合成标题化合物。