1,3,8-triacetoxy-6-iodomethyl-anthraquinone | 196865-22-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,3,8-triacetoxy-6-iodomethyl-anthraquinone
• 英文别名: [4,5-diacetyloxy-7-(iodomethyl)-9,10-dioxoanthracen-2-yl] acetate
• CAS: 196865-22-2
• 化学式: C₂₁H₁₅IO₈
• 分子量: 522.25
• InChiKey: SZZXNZCSWGGHHU-UHFFFAOYSA-N

物化性质

• 沸点：
  655.0±55.0 °C(Predicted)
• 密度：
  1.700±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,3,8-triacetoxy-6-iodomethyl-anthraquinone 在 盐酸 、 硫酸 、 silver trifluoromethanesulfonate 、 三氯化铁 、 tin(ll) chloride 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 25.33h， 生成 2,4,5,2',4',5'-Hexahydroxy-7,7'-bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxymethyl)-9H,9'H-[9,9']bianthracenyl-10,10'-dione
  参考文献：
  名称：

  Concerning the enantiomerization barrier of hypericin

  摘要：

  The Syntheses of omega-(R)-menthyl and omega,omega-bis-(R)-menthyl derivatives 2 and 3 of hypericin were achieved, and the corresponding diastereomers could be separated. The equilibria between the respective diastereomers are slightly displaced in favor of the chromatographically faster moving ones. Kinetic measurements on these easily equilibrating diastereomers of 2 and 3 provided an Arrhenius activation energy for the interconversion barrier between the two propeller conformers of 83 and 89 kJ/mol. It could be shown that the omega-menthyl residues are of minor relevance to the height of this barrier, as is also the case for the bay hydroxyl ionization and quinone tautomerization equilibria. It was thus concluded that the intrinsic barrier for the propeller conformer enantiomerization of hypericin is in the order of 80 kJ/mol. These results are in accord with those obtained from semiempirical calculations.

  DOI：

  10.1007/bf00810772
• 作为产物：
  描述：

  6-bromomethyl-1,3,8-triacetoxyanthracene-9,10-dione 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 1.5h， 以93%的产率得到1,3,8-triacetoxy-6-iodomethyl-anthraquinone
  参考文献：
  名称：

  Concerning the enantiomerization barrier of hypericin

  摘要：

  The Syntheses of omega-(R)-menthyl and omega,omega-bis-(R)-menthyl derivatives 2 and 3 of hypericin were achieved, and the corresponding diastereomers could be separated. The equilibria between the respective diastereomers are slightly displaced in favor of the chromatographically faster moving ones. Kinetic measurements on these easily equilibrating diastereomers of 2 and 3 provided an Arrhenius activation energy for the interconversion barrier between the two propeller conformers of 83 and 89 kJ/mol. It could be shown that the omega-menthyl residues are of minor relevance to the height of this barrier, as is also the case for the bay hydroxyl ionization and quinone tautomerization equilibria. It was thus concluded that the intrinsic barrier for the propeller conformer enantiomerization of hypericin is in the order of 80 kJ/mol. These results are in accord with those obtained from semiempirical calculations.

  DOI：

  10.1007/bf00810772

文献信息

• Synthesis and Properties of Hypericins Substituted with Acidic and Basic Residues: Hypericin Tetrasulfonic Acid – A Water Soluble Hypericin Derivative
  作者：Heinz Falk、Abd-El-Wareth A. O. Sarhan、Huyen T. N. Tran、Robert Altmann

  DOI：10.1007/pl00000089

  日期：1998.3

  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.