1,3,8-Trihydroxy-6-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxymethyl)-anthraquinone | 196865-23-3

• 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-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxymethyl)-anthraquinone
• 英文别名: 1,3,8-trihydroxy-6-[[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxymethyl]anthracene-9,10-dione
• CAS: 196865-23-3
• 化学式: C₂₅H₂₈O₆
• 分子量: 424.494
• InChiKey: NLGGZMLWZXADJV-ZQWRNJAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,3,8-Trihydroxy-6-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxymethyl)-anthraquinone 在 盐酸 、 三氯化铁 、 tin(ll) chloride 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 11.33h， 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 硫酸 、 silver trifluoromethanesulfonate 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 23.5h， 生成 1,3,8-Trihydroxy-6-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxymethyl)-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

• Concerning the enantiomerization barrier of hypericin
  作者：R. Altmann、C. Etzlstorfer、H. Falk

  DOI：10.1007/bf00810772

  日期：1997.4

  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.