1,3,8-Trihydroxy-6-octyloxymethyl-10H-anthracene-9-one | 171782-01-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,3,8-Trihydroxy-6-octyloxymethyl-10H-anthracene-9-one
• CAS: 171782-01-7
• 化学式: C₂₃H₂₈O₅
• 分子量: 384.472
• InChiKey: UXODTOHJOMHBRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  86.99
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1,3,8-Trihydroxy-6-octyloxymethyl-10H-anthracene-9-one 在 哌啶 、 吡啶-N-氧化物 、 iron(II) sulfate 作用下， 以 吡啶 为溶剂， 反应 2.0h， 以13%的产率得到1,3,4,6,8,13-Hexahydroxy-10,11-bis-octyloxymethyl-phenanthro<1,10,9,8-o,p,q,r,a>perylene-7,14-dione
  参考文献：
  名称：

  On the synthesis of ?-appended hypericin derivatives

  摘要：

  A method for the preparation of bis-omega-appended hypericin derivatives bearing n-octyl n-hexadecyl, and 2-(2-(2-hydroxyethoxy)-ethoxy)-ethoxymethyl substituents was developed. The key step - the synthesis of appropriately omega-substituted emodin derivatives - was achieved by solvolyzing 3-bromomethyl-1,6,8-triacetyloxy-anthracene-9,10-dione (omega-bromo triacetylemodin) in an appropriate alcohol in the presence of silver perchlorate. The corresponding bis-omega-substituted hypericins were then prepared conventionally by dimerizing the omega-substituted emodin anthrones. The latter were prepared by reduction of the omega-appended emodins.

  DOI：

  10.1007/bf00811019
• 作为产物：
  描述：

  6-bromomethyl-1,3,8-triacetoxyanthracene-9,10-dione 在 盐酸 、 silver perchlorate 、 tin(ll) chloride 作用下， 以 溶剂黄146 为溶剂， 反应 11.0h， 生成 1,3,8-Trihydroxy-6-octyloxymethyl-10H-anthracene-9-one
  参考文献：
  名称：

  On the synthesis of ?-appended hypericin derivatives

  摘要：

  A method for the preparation of bis-omega-appended hypericin derivatives bearing n-octyl n-hexadecyl, and 2-(2-(2-hydroxyethoxy)-ethoxy)-ethoxymethyl substituents was developed. The key step - the synthesis of appropriately omega-substituted emodin derivatives - was achieved by solvolyzing 3-bromomethyl-1,6,8-triacetyloxy-anthracene-9,10-dione (omega-bromo triacetylemodin) in an appropriate alcohol in the presence of silver perchlorate. The corresponding bis-omega-substituted hypericins were then prepared conventionally by dimerizing the omega-substituted emodin anthrones. The latter were prepared by reduction of the omega-appended emodins.

  DOI：

  10.1007/bf00811019