[7-(2-acetamidoethoxymethyl)-4,5-diacetyloxy-9,10-dioxoanthracen-2-yl] acetate | 205384-00-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: [7-(2-acetamidoethoxymethyl)-4,5-diacetyloxy-9,10-dioxoanthracen-2-yl] acetate
• CAS: 205384-00-5
• 化学式: C₂₅H₂₃NO₁₀
• 分子量: 497.458
• InChiKey: GIEFKABNZXLONC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.89
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  151.37
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  [7-(2-acetamidoethoxymethyl)-4,5-diacetyloxy-9,10-dioxoanthracen-2-yl] acetate 在 盐酸 、 tin(ll) chloride 作用下， 以 溶剂黄146 、 丙酮 为溶剂， 反应 4.67h， 生成 N-[2-(4,5,7-Trihydroxy-10-oxo-9,10-dihydro-anthracen-2-ylmethoxy)-ethyl]-acetamide
  参考文献：
  名称：

  Synthesis and Properties of Hypericins Substituted with Acidic and Basic Residues: Hypericin Tetrasulfonic Acid – A Water Soluble Hypericin Derivative

  摘要：

  Sulfonation of hypericin leads to its di-, tri-, and tetrasulfonic acid derivatives. The latter is soluble in water up to millimolar solutions. Homoaggregate formation (J-aggregates) was observed only above 5.10(-4) mol/l. In water solutions, the tetrasulfonic acid hypericin derivative was found to be present as its bay-phenolate with most of the sulphonic acids dissociated. Thus, the first water soluble hypericin derivative, which in contrast to hypericin is not prone to homoassociation, is presented. Hypericin tetrtasulfonic acid forms heteroassociates with serum albumin, DNA, and gamma-cyclodextrin. Hypericin derivatives with primary and tertiary amino group appendages at the hypericin methyl groups were synthesized. However, upon salt formation or quaternization these derivatives became virtually insoluble in all common solvents including water.

  DOI：

  10.1007/pl00000089
• 作为产物：
  描述：

  N-乙酰乙醇胺 、 1,3,8-triacetoxy-6-iodomethyl-anthraquinone 在 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以37%的产率得到[7-(2-acetamidoethoxymethyl)-4,5-diacetyloxy-9,10-dioxoanthracen-2-yl] acetate
  参考文献：
  名称：

  Synthesis and Properties of Hypericins Substituted with Acidic and Basic Residues: Hypericin Tetrasulfonic Acid – A Water Soluble Hypericin Derivative

  摘要：

  Sulfonation of hypericin leads to its di-, tri-, and tetrasulfonic acid derivatives. The latter is soluble in water up to millimolar solutions. Homoaggregate formation (J-aggregates) was observed only above 5.10(-4) mol/l. In water solutions, the tetrasulfonic acid hypericin derivative was found to be present as its bay-phenolate with most of the sulphonic acids dissociated. Thus, the first water soluble hypericin derivative, which in contrast to hypericin is not prone to homoassociation, is presented. Hypericin tetrtasulfonic acid forms heteroassociates with serum albumin, DNA, and gamma-cyclodextrin. Hypericin derivatives with primary and tertiary amino group appendages at the hypericin methyl groups were synthesized. However, upon salt formation or quaternization these derivatives became virtually insoluble in all common solvents including water.

  DOI：

  10.1007/pl00000089