1,5,8,8-tetramethyl-8-bicyclo<8.1.0>undecene-2,9-diol | 142722-69-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,5,8,8-tetramethyl-8-bicyclo<8.1.0>undecene-2,9-diol
• 英文别名: (1R,2S,5E,9S,10S)-1,5,8,8-tetramethylbicyclo[8.1.0]undec-5-ene-2,9-diol
• CAS: 142722-69-8
• 化学式: C₁₅H₂₆O₂
• 分子量: 238.37
• InChiKey: RKDPETZBSSPSSM-SSHMBCCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,5,8,8-tetramethyl-8-bicyclo<8.1.0>undecene-2,9-diol 、 三甲基硅咪唑 在 吡啶 作用下， 反应 0.5h， 生成 trimethyl-[[(1R,2S,5E,9S,10S)-1,5,8,8-tetramethyl-9-trimethylsilyloxy-2-bicyclo[8.1.0]undec-5-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
• 作为产物：
  描述：

  humulene 9,10-epoxide 在 溶剂黄146 potassium dihydrogenphosphate 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以14.3%的产率得到4,8-Cycloundecadiene-1,2-diol, 2,6,6,9-tetramethyl-, (1R*,2S*,4E,8E)-
  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

文献信息

• Hydrolysis and reversible isomerization of humulene epoxides II and III.
  作者：Xiaogen Yang、Max L. Deinzer

  DOI：10.1021/jo00043a033

  日期：1992.8

  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).