methyl (1R,3R)-2-[2-(7-hydroxy-3-isopropyl-9,10-dioxo-9,10-dihydroanthracen-1-yl)ethyl]-1,3-dimethyl-3-vinylcyclohexane-1-carboxylate | 1185024-78-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: methyl (1R,3R)-2-[2-(7-hydroxy-3-isopropyl-9,10-dioxo-9,10-dihydroanthracen-1-yl)ethyl]-1,3-dimethyl-3-vinylcyclohexane-1-carboxylate
• CAS: 1185024-78-5
• 化学式: C₃₁H₃₆O₅
• 分子量: 488.624
• InChiKey: KFMUPBOTNHKCLO-SDDUWZMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  36.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  80.67
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  methyl 8-hydroxy-24-isopropyl-5,9-dimethyl-14,21-dioxohexacyclo[10.6.2.0^1,10.0^4,9.0^13,22..0^15,20]tetracosa-13(22),15,17,19-tetraene-5-caboxylate 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以0.22 g的产率得到methyl (1R,3R)-2-[2-(7-hydroxy-3-isopropyl-9,10-dioxo-9,10-dihydroanthracen-1-yl)ethyl]-1,3-dimethyl-3-vinylcyclohexane-1-carboxylate
  参考文献：
  名称：

  Synthetic transformations of higher terpenoids: XVIII. Synthesis of optically active 9,10-anthraquinone derivatives

  摘要：

  Retro-Diels-Alder decomposition of dodecahydro-endo-4b,12-ethenochrysene-1,4-diones obtained from a tricyclic diterpenoid, levopimaric acid, gave optically active 5-[2-(6-vinyl-2,6-dimethyl-2-carboxycyclohexyl) ethyl]-7-isopropyl-1,4-naphthoquinones which reacted with silyloxybutadienes to produce the corresponding 6- and 7-hydroxyanthraquinones, 5-furyl-7-hydroxytetrahydroanthraquinones, or 5-furyl-7-oxohexahydroanthraquinones. Condensation of the naphthoquinone derivatives with 5-isopropenyl-2,3-dihydrothiophene 1,1-dioxide resulted in the formation of 6,11-dioxodihydro- and 6,11-dioxohexahydroanthra[2,1-b]thiophene 3,3-dioxides. 6- and 7-Hydroxyanthraquinones were also obtained by reaction of dodecahydro-endo-4b,12-ethenochrysene-1,4-diones with Danishevsky diene, followed by cleavage of the polycyclic adducts. The cycloaddition of 5-[2-(-2-carboxy-2,6-dimethyl-6-vinylcyclohexyl)ethyl]-7-isopropyl-1,4-naphthoquinones in the presence of Lewis acids was characterized by increased regioselectivity.

  DOI：

  10.1134/s1070428009010138