(1R,3R)-2-[2-(3-isopropyl-5,8-dioxo-5,8-dihydronaphthalen-1-yl)ethyl]-1,3-dimethyl-3-vinylcyclohexane-1-carboxylic acid | 1185024-72-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1R,3R)-2-[2-(3-isopropyl-5,8-dioxo-5,8-dihydronaphthalen-1-yl)ethyl]-1,3-dimethyl-3-vinylcyclohexane-1-carboxylic acid
• CAS: 1185024-72-9
• 化学式: C₂₆H₃₂O₄
• 分子量: 408.538
• InChiKey: WFPUTQGHFILMKK-ZSQFBXSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.44
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R,3R)-2-[2-(3-isopropyl-5,8-dioxo-5,8-dihydronaphthalen-1-yl)ethyl]-1,3-dimethyl-3-vinylcyclohexane-1-carboxylic acid 、 1-甲氧基-3-三甲基硅氧基-1,3-丁二烯 在 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 30.0h， 以55%的产率得到(1R,3R)-2-[2-(7-hydroxy-3-isopropyl-9,10-dioxo-9,10-dihydroanthracen-1-yl)ethyl]-1,3-dimethyl-3-vinylcyclohexane-1-carboxylic acid
  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
• 作为产物：
  描述：

  20-isopropyl-5,9-dimethyl-14,17-dioxopentacyco[10.6.2.0^1,10.0^4,9.0^13,18]icosa-13(18),15,19-triene-5-caboxylic acid 以 1,4-二氧六环 为溶剂， 反应 10.0h， 以97%的产率得到(1R,3R)-2-[2-(3-isopropyl-5,8-dioxo-5,8-dihydronaphthalen-1-yl)ethyl]-1,3-dimethyl-3-vinylcyclohexane-1-carboxylic acid
  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

文献信息

• Synthetic transformations of higher terpenoids: XVIII. Synthesis of optically active 9,10-anthraquinone derivatives
  作者：E. E. Shul’ts、D. S. Oleinikov、I. V. Nechepurenko、M. M. Shakirov、G. A. Tolstikov

  DOI：10.1134/s1070428009010138

  日期：2009.1

  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.