4,10-香木兰烷二醇 | 70051-38-6

• 物质功能分类: 天然产物 - 倍半萜
• 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
• 中文名称: 4,10-香木兰烷二醇
• 英文名称: 4β,10α-aromadendranediol
• 英文别名: 4β,10α-dihydroxyaromadendrane；4,10-Aromadendranediol；(1aR,4R,4aR,7S,7aS,7bR)-1,1,4,7-tetramethyl-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[h]azulene-4,7-diol
• CAS: 70051-38-6
• 化学式: C₁₅H₂₆O₂
• 分子量: 238.37
• InChiKey: DWNPMJOWAWGIMM-HTKHVQBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (+)-11β-hydroxy-apoaromadendrone 在 Oxone 、 lithium aluminium tetrahydride 、 18-冠醚-6 、 硫酸 、 碘 、 碳酸氢钠 、 magnesium 、 丙酮 作用下， 反应 2.0h， 生成 4,10-香木兰烷二醇
  参考文献：
  名称：

  The synthesis of mono- and dihydroxy aromadendrane sesquiterpenes, starting from natural (+)-aromadendrene-III

  摘要：

  The monoalcohols (-)-globulol (2), (-)-epiglobulol (3), (-)-ledol (4), and (+)-viridiflorol (5) were synthesized from (+)-aromadendrene (1). The cis-fused alloaromadendrone (14), the key intermediate used in the synthesis of 4 and 5, was obtained from the trans-fused apoaromadendrone (13) via a selective protonation of the thermodynamic enol trimethylsilylether 15. After hydroxylation of the tertiary C11 of 13 with RuO4, (+)-spathulenol (6), (-)-allospathulenol (7), and the aromadendrane diols 8-11 could be prepared. Compounds 2-11 were tested for antifungal properties, but their activity was only moderate.

  DOI：

  10.1016/s0040-4020(01)88765-2

文献信息

• Four heliangolides and other sesquiterpenes from Brasilia sickii
  作者：Ferdinand Bohlmann、Michael Grenz、Jasmin Jakupovic、Robert M. King、Harold Robinson

  DOI：10.1016/0031-9422(83)80224-6

  日期：1983.1

  Abstract The investigation of Brasilia sickii afforded, in addition to known compounds, two new bisabolene derivatives, an acetate closely related to damsin

  摘要 除已知化合物外，对巴西利亚病菌的研究还提供了两种新的红没药烯衍生物，一种与大黄素密切相关的醋酸盐。
• Terpenoids-LXXIV
  作者：Curtis M. Beechan、Carl Djerassi、Hanne Eggert

  DOI：10.1016/0040-4020(78)88378-1

  日期：1978.1
• The synthesis of mono- and dihydroxy aromadendrane sesquiterpenes, starting from natural (+)-aromadendrene-III
  作者：Harrie J.M. Gijsen、Joannes B.P.A. Wijnberg、Gerrit A. Stork、Aede de Groot、Maarten A. de Waard、Johannes G.M. van Nistelrooy

  DOI：10.1016/s0040-4020(01)88765-2

  日期：1992.3

  The monoalcohols (-)-globulol (2), (-)-epiglobulol (3), (-)-ledol (4), and (+)-viridiflorol (5) were synthesized from (+)-aromadendrene (1). The cis-fused alloaromadendrone (14), the key intermediate used in the synthesis of 4 and 5, was obtained from the trans-fused apoaromadendrone (13) via a selective protonation of the thermodynamic enol trimethylsilylether 15. After hydroxylation of the tertiary C11 of 13 with RuO4, (+)-spathulenol (6), (-)-allospathulenol (7), and the aromadendrane diols 8-11 could be prepared. Compounds 2-11 were tested for antifungal properties, but their activity was only moderate.