(+)-(1S,2S,4aS,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-2-hydroxy-1-(hydroxymethyl)-1,4a-dimethyl-5,8-dimethoxy-7-isopropylphenanthrene | 155320-96-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (+)-(1S,2S,4aS,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-2-hydroxy-1-(hydroxymethyl)-1,4a-dimethyl-5,8-dimethoxy-7-isopropylphenanthrene
• 英文别名: (1S,2S,4aS,10aR)-1-(hydroxymethyl)-5,8-dimethoxy-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-2-ol
• CAS: 155320-96-0
• 化学式: C₂₂H₃₄O₄
• 分子量: 362.51
• InChiKey: COKVODORBFFHHO-JZZBYWGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-(1S,2S,4aS,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-2-hydroxy-1-(hydroxymethyl)-1,4a-dimethyl-5,8-dimethoxy-7-isopropylphenanthrene 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 以86%的产率得到triptoquinone C
  参考文献：
  名称：

  Enantiocontrolled total synthesis of the diterpenoids, triptoquinone B, C and triptocallol

  摘要：

  An efficient and enantiocontrolled synthesis of triptoquinone B and C, which possess interleukin-1 inhibitory activity, has been accomplished employing the lipase-catalyzed kinetic resolution and a highly diastereoselective radical cyclization as key synthetic steps. In addition, the first total synthesis of triptocallol has been achieved utilizing the same strategy. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00841-1
• 作为产物：
  描述：

  雷藤二萜醌 B 在 lithium aluminium tetrahydride 、 sodium dithionite 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 4.5h， 生成 (+)-(1S,2S,4aS,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-2-hydroxy-1-(hydroxymethyl)-1,4a-dimethyl-5,8-dimethoxy-7-isopropylphenanthrene
  参考文献：
  名称：

  Synthetic studies on diterpenoid quinones with interleukin-1 inhibitory activity. Total synthesis of (.+-.)- and (+)-triptoquinone A

  摘要：

  An efficient first total synthesis of (+/-)- and (+)-triptoquinone A (1), a novel diterpenoid quinone with significant inhibitory activity against interleukin-1 releases, has been completed. Birch reduction of tricyclic enone (+/-)-7, prepared from known 6-methoxy-2-isopropyl-1-naphthol (22), which is readily available in large quantities, was followed by immediate enolate trapping to provide silyl enol ether (+/-)-30. Compound 30 was converted into carboxylic acid (+/-)-4 via the corresponding enol triflate (+/-)-31 either by sequential palladium-catalyzed carbonylation and oxidation or by direct carboxylation. The total synthesis of (+/-)-1 was completed by oxidation of (+/-)-4 with CAN in 12 steps from 22 in 19% overall yield at best. A second, enantioselective total synthesis of (+)-1 was accomplished via (+/-)-7, which was prepared by (-)-N- [4-(trifluoromethyl)benzyl]cinchonidinium bromide (33) catalyzed asymmetric Michael reaction of 6 with ethyl vinyl ketone and a subsequent aldol condensation. The absolute structures of triptoquinone B (2) and C (3), which were isolated concomitantly with triptoquinone A from the same plant sources, were established by a series of chemical reactions based on (+)-7.

  DOI：

  10.1021/jo00081a021