1-(hydroxymethyl)-3-methylanthracene-9,10-dione | 1204036-63-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-(hydroxymethyl)-3-methylanthracene-9,10-dione
• CAS: 1204036-63-4
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: VOONMAPNDRSROV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-Hydroxy-11-methyl-15,16-dioxatetracyclo[7.7.1.02,7.013,17]heptadeca-2,4,6,9,11,13(17)-hexaen-8-one 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以7 mg的产率得到1-(hydroxymethyl)-3-methylanthracene-9,10-dione
  参考文献：
  名称：

  Photochemical Hydroxylation of 1-Methyl-9,10-anthraquinones: Synthesis of 9′-Hydroxyaloesaponarin II

  摘要：

  Photolysis of 1-methyl-9,10-anthraquinones in the presence of oxygen yields endoperoxides that can be reduced to produce 1-hydroxymethyl-9,10-anthraquinones. The reaction proceeds in a fashion similar to that or other o-alkylphenones which yield either a 1,4-diradical or a "photoenol" upon irradiation. Anthraquinones undergo photochemistry at a wavelength where the endoperoxide is transparent, allowing, its isolation. A singlet oxygen quencher had no effect on the rate of formation of the endoperoxide. The photochemical hydroxylation has been used in a total synthesis of a naturally occurring polyketide, 9'-hydroxyaloesaponarin II.

  DOI：

  10.1021/jo902247v

文献信息

• Photochemical Hydroxylation of 1-Methyl-9,10-anthraquinones: Synthesis of 9′-Hydroxyaloesaponarin II
  作者：Salwa Elkazaz、Paul B. Jones

  DOI：10.1021/jo902247v

  日期：2010.1.15

  Photolysis of 1-methyl-9,10-anthraquinones in the presence of oxygen yields endoperoxides that can be reduced to produce 1-hydroxymethyl-9,10-anthraquinones. The reaction proceeds in a fashion similar to that or other o-alkylphenones which yield either a 1,4-diradical or a "photoenol" upon irradiation. Anthraquinones undergo photochemistry at a wavelength where the endoperoxide is transparent, allowing, its isolation. A singlet oxygen quencher had no effect on the rate of formation of the endoperoxide. The photochemical hydroxylation has been used in a total synthesis of a naturally occurring polyketide, 9'-hydroxyaloesaponarin II.