4,8,11,11-tetramethyl-8-tricyclo<7.2.0.0^2,5>undecen-4-ol | 142722-67-6

• 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: 4,8,11,11-tetramethyl-8-tricyclo<7.2.0.0^2,5>undecen-4-ol
• 英文别名: (1R,2S,4S,5S)-4,8,11,11-tetramethyltricyclo[7.2.0.02,5]undec-8-en-4-ol
• CAS: 142722-67-6
• 化学式: C₁₅H₂₄O
• 分子量: 220.355
• InChiKey: HOGDSHVBAIOKEB-COMQUAJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4,8,11,11-tetramethyl-8-tricyclo<7.2.0.0^2,5>undecen-4-ol 、 三甲基硅咪唑 在 吡啶 作用下， 反应 0.5h， 生成 trimethyl-[[(1S,2R,4R,5R)-4,8,11,11-tetramethyl-4-tricyclo[7.2.0.02,5]undec-8-enyl]oxy]silane
  参考文献：
  名称：

  Hydrolysis and reversible isomerization of humulene epoxides II and III.

  摘要：

  The hydrolysis reactions of humulene epoxide II (3) and humulene epoxide III (4) were studied in aqueous solution at pH 4.0. Twelve compounds from the hydrolysis of humulene epoxide II and 16 from humulene epoxide III were separated and identified. All of the compounds identified from hydrolysis of 3 also were found among the hydrolysis products of 4. A reversible transformation between these two epoxides proceeding through a bicyclic diol (15) as intermediate is responsible for producing the same products. Hydrolysis reactions further yielded diols and a number of different ring systems. The apparent intermediacy of carbocations also led to several elimination reaction products. Among the products identified from these epoxides, six have not been reported before. These are 1,5,8,8-tetramethyl-12-oxa-5-tricyclo[7.2.1.0(6,9)]dodecene (1), 4,8,11,11-tetramethyl-8-tricyclo-[7.2.0.0(2,5)]undecen-4-ol (5), stereoisomers of 2,6,6,9-tetramethyltricyclo[6.3.0.0(2,4)]undecane-5,9-diol (10, 14), 1,5,8,8-tetramethyl-8-bicyclo[8.1.0]undecene-2,9-diol (15), and the stereoisomeric pair 4,8,11,11-tetramethyl-tricyclo[6.3.0.0(2,4)]undecane-5,9-diol (16).

  DOI：

  10.1021/jo00043a033