1,3,8-trimethoxy-6-amino-9,10-anthraquinone | 883125-70-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,3,8-trimethoxy-6-amino-9,10-anthraquinone
• 英文别名: 9,10-Anthracenedione, 3-amino-1,6,8-trimethoxy-；3-amino-1,6,8-trimethoxyanthracene-9,10-dione
• CAS: 883125-70-0
• 化学式: C₁₇H₁₅NO₅
• 分子量: 313.31
• InChiKey: AEAARGZECLRCMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  87.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,3,8-trimethoxy-6-amino-9,10-anthraquinone 在 氢溴酸 、 tin(ll) chloride 作用下， 以 1,4-二氧六环 、 吡啶 、 溶剂黄146 为溶剂， 反应 3.5h， 生成 1,3,8-trihydroxy-6-(acetylamino)-10H-anthracen-9-one
  参考文献：
  名称：

  A Route to Amino Functionalized Hypericin Derivatives and their Chemical and Photochemical Properties Pertaining to Photodynamic Therapy

  摘要：

  Syntheses of amino functionalized hypericin derivatives could be achieved starting from the recently prepared emodin derived 1,3,8-trimethoxy-6-amino-9,10-anthraquinone. Our strategies for the preparation of 10,11-didemethyl-10,11-diaminohypericin, 10,11-didemethyl-10,11-di(acetylamino) hypericin, and its hypericinoidic diazepine derivative include synthetical modifications on the levels of the anthraquinone, anthron, and the phenanthroperylenequinone system itself. The chemical as well as photochemical properties of these unique hypericin derivatives, which might constitute new photodynamic therapy agents, are reported.

  DOI：

  10.1007/s00706-005-0397-5
• 作为产物：
  描述：

  4,5,7-trimethoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid 在 氢氧化钾 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 26.75h， 生成 1,3,8-trimethoxy-6-amino-9,10-anthraquinone
  参考文献：
  名称：

  An Efficient Route to Emodic Amine and Analogous O-Methyl Protected Derivatives Starting from Emodin

  摘要：

  Emodic amine could be synthesized in a five-step approach in excellent overall yield by following a modified Curtius rearrangement strategy, starting from the naturally occurring emodin. This unique emodin derived 6-amino substituted polyhydroxylated anthraquinone may serve as a promising synthon for a new class of amino functionalized photodynamically active hypericin derivatives. In addition, the partially O-methyl protected 6-amino- and 6-carboxy-anthraquinones could be synthesized in high yields via selective O-methyl ether cleavage from the corresponding tri-O-methyl derivatives.

  DOI：

  10.1007/s00706-005-0350-7

文献信息

• Shibata, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1941, vol. 61, p. 320,324; dtsch. Ref. S. 103, 106
  作者：Shibata

  DOI：——

  日期：——
• An Efficient Route to Emodic Amine and Analogous O-Methyl Protected Derivatives Starting from Emodin
  作者：Bernd Lackner、Klaus Bretterbauer、Heinz Falk

  DOI：10.1007/s00706-005-0350-7

  日期：2005.9

  Emodic amine could be synthesized in a five-step approach in excellent overall yield by following a modified Curtius rearrangement strategy, starting from the naturally occurring emodin. This unique emodin derived 6-amino substituted polyhydroxylated anthraquinone may serve as a promising synthon for a new class of amino functionalized photodynamically active hypericin derivatives. In addition, the partially O-methyl protected 6-amino- and 6-carboxy-anthraquinones could be synthesized in high yields via selective O-methyl ether cleavage from the corresponding tri-O-methyl derivatives.
• A Route to Amino Functionalized Hypericin Derivatives and their Chemical and Photochemical Properties Pertaining to Photodynamic Therapy
  作者：Bernd Lackner、Klaus Bretterbauer、Clemens Schwarzinger、Heinz Falk

  DOI：10.1007/s00706-005-0397-5

  日期：2005.12

  Syntheses of amino functionalized hypericin derivatives could be achieved starting from the recently prepared emodin derived 1,3,8-trimethoxy-6-amino-9,10-anthraquinone. Our strategies for the preparation of 10,11-didemethyl-10,11-diaminohypericin, 10,11-didemethyl-10,11-di(acetylamino) hypericin, and its hypericinoidic diazepine derivative include synthetical modifications on the levels of the anthraquinone, anthron, and the phenanthroperylenequinone system itself. The chemical as well as photochemical properties of these unique hypericin derivatives, which might constitute new photodynamic therapy agents, are reported.