Trimethylemodin anthrone | 138370-20-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: Trimethylemodin anthrone
• 英文别名: 1,3-8-trimethoxy-6-methylanthracen-9-ol；9-Anthracenol, 1,3,8-trimethoxy-6-methyl-；1,3,8-trimethoxy-6-methylanthracen-9-ol
• CAS: 138370-20-4
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: ALZTXUMPWBTBRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Trimethylemodin anthrone 在 氢氧化钾 、 dipotassium peroxodisulfate 、 三氯化铁 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 Z-1,1',3,3',9,9'-Hexamethoxy-7,7'-dimethylbianthrone
  参考文献：
  名称：

  On the synthesis of hypericin by oxidative trimethylemodin anthrone and emodin anthrone dimerization: Isohypericin

  摘要：

  The base catalyzed oxidative dimerization of emodin anthrone exclusively yields hypericin. However, on oxidative dimerization of trimethylemodinanthrone a mixture of hexamethylhypericin and hexamethylisohypericin was obtained. Chromatographic separation of the hexabenzoyl derivatives was achieved, and by saponification about equal amounts of hypericin and isohypericrin were produced. Isohypericin could be characterized for the first time by its spectroscopic data and its protonation and deprotonation pK(a) and pK(a)* values.

  DOI：

  10.1007/bf00811548
• 作为产物：
  描述：

  3,5-二甲氧基苯甲醛 在 palladium on activated charcoal 盐酸 、 四甲基乙二胺 、 硫酸 、 氢气 、 仲丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， -80.0~45.0 ℃ 、500.0 kPa 条件下， 反应 16.67h， 生成 Trimethylemodin anthrone
  参考文献：
  名称：

  A synthesis of emodin anthrone

  摘要：

  A novel high yield (74% overall) synthesis of five steps to prepare emodin anthrone, which serves as a valuable precursor of hypericin, was devised using the benzamide ortho lithiation strategy for the key step.

  DOI：

  10.1007/bf00811474

文献信息

• On the synthesis of hypericin by oxidative trimethylemodin anthrone and emodin anthrone dimerization: Isohypericin
  作者：Heinz Falk、Gerhard Schoppel

  DOI：10.1007/bf00811548

  日期：1992.10

  The base catalyzed oxidative dimerization of emodin anthrone exclusively yields hypericin. However, on oxidative dimerization of trimethylemodinanthrone a mixture of hexamethylhypericin and hexamethylisohypericin was obtained. Chromatographic separation of the hexabenzoyl derivatives was achieved, and by saponification about equal amounts of hypericin and isohypericrin were produced. Isohypericin could be characterized for the first time by its spectroscopic data and its protonation and deprotonation pK(a) and pK(a)* values.
• A synthesis of emodin anthrone
  作者：Heinz Falk、Gerhard Schoppel

  DOI：10.1007/bf00811474

  日期：——

  A novel high yield (74% overall) synthesis of five steps to prepare emodin anthrone, which serves as a valuable precursor of hypericin, was devised using the benzamide ortho lithiation strategy for the key step.