Isohypericin | 41689-58-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: Isohypericin
• 英文别名: 5,7,11,16,18,22-hexahydroxy-13,24-dimethyloctacyclo[13.11.1.12,10.03,8.04,25.019,27.021,26.014,28]octacosa-1(26),2,4(25),5,7,10,12,14(28),15(27),16,18,21,23-tridecaene-9,20-dione
• CAS: 41689-58-1
• 化学式: C₃₀H₁₆O₈
• 分子量: 504.452
• InChiKey: YWRCOVRJJXHFBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  38
• 可旋转键数：
  0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  156
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  Isohypericinhexabenzoate 在 氢氧化钾 作用下， 反应 0.33h， 以93%的产率得到Isohypericin
  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

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.