(-)-15-hydroxy-trans-maali-9-one | 157275-50-8

• 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: (-)-15-hydroxy-trans-maali-9-one
• 英文别名: (1aR,3aS,7R,7aS,7bR)-3a-(hydroxymethyl)-1,1,7-trimethyl-1a,2,3,5,6,7,7a,7b-octahydrocyclopropa[a]naphthalen-4-one
• CAS: 157275-50-8
• 化学式: C₁₅H₂₄O₂
• 分子量: 236.354
• InChiKey: YWAUHULOQHCKCJ-VEQZDLLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-15-hydroxy-trans-maali-9-one 在 正丁基锂 、 四甲基乙二胺 、 bis(dimethylamino)chlorophosphoramidate 、 lithium 、 sodium cyanoborohydride 、 乙胺 、 zinc(II) chloride 作用下， 以 甲醇 为溶剂， 反应 7.5h， 生成 (-)-trans-maaliane
  参考文献：
  名称：

  Rearrangement reactions of aromadendrane derivatives. The synthesis of (+)-maaliol, starting from natural (+)-aromadendrene-IV

  摘要：

  Starting from the hydroazulene alpha-ketol 6, which can easily be prepared from (+)-aromadendrene (1), two different routes to hydronaphthalene compounds with a maaliane skeleton have been developed, both proceeding in high overall yield. The first route leads to cis-fused maaliane derivatives; the second one offers access to trans-fused maaliane sesquiterpenes, as demonstrated in this paper in the synthesis of (+)-maaliol (5).

  DOI：

  10.1016/s0040-4020(01)85012-2
• 作为产物：
  描述：

  [(1aR,4R,4aR,7R,7aS,7bR)-1,1,7-trimethylspiro[1a,2,3,5,6,7,7a,7b-octahydrocyclopropa[h]azulene-4,2'-oxirane]-4a-yl]oxy-trimethylsilane 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以94%的产率得到(-)-15-hydroxy-trans-maali-9-one
  参考文献：
  名称：

  Rearrangement reactions of aromadendrane derivatives. The synthesis of (+)-maaliol, starting from natural (+)-aromadendrene-IV

  摘要：

  Starting from the hydroazulene alpha-ketol 6, which can easily be prepared from (+)-aromadendrene (1), two different routes to hydronaphthalene compounds with a maaliane skeleton have been developed, both proceeding in high overall yield. The first route leads to cis-fused maaliane derivatives; the second one offers access to trans-fused maaliane sesquiterpenes, as demonstrated in this paper in the synthesis of (+)-maaliol (5).

  DOI：

  10.1016/s0040-4020(01)85012-2

文献信息

• Rearrangement reactions of aromadendrane derivatives. The synthesis of (+)-maaliol, starting from natural (+)-aromadendrene-IV
  作者：Harrie J.M. Gijsen、Joannes B.P.A. Wijnberg、Connie van Ravenswaay、Aede de Groot

  DOI：10.1016/s0040-4020(01)85012-2

  日期：1994.4

  Starting from the hydroazulene alpha-ketol 6, which can easily be prepared from (+)-aromadendrene (1), two different routes to hydronaphthalene compounds with a maaliane skeleton have been developed, both proceeding in high overall yield. The first route leads to cis-fused maaliane derivatives; the second one offers access to trans-fused maaliane sesquiterpenes, as demonstrated in this paper in the synthesis of (+)-maaliol (5).