Humulenol-II | 80408-11-3

• 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: Humulenol-II
• 英文别名: (4E,8E)-6,6,9-trimethyl-2-methylidenecycloundeca-4,8-dien-1-ol
• CAS: 80408-11-3
• 化学式: C₁₅H₂₄O
• 分子量: 220.355
• InChiKey: ZHCPVYWHSOILQL-VKLURXMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  大麻 在 过氧化氢苯甲酰 、 askanite-bentonite clay 、 氢气 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 5.0h， 生成 Humulenol-II
  参考文献：
  名称：

  Khomenko; Zenkovets; Barkhash, Russian Journal of Organic Chemistry, 1997, vol. 33, # 5, p. 595 - 600

  摘要：

  DOI：

文献信息

• 5,9-Dihydroxy-4,8,11,11-tetramethyltricyclo[6.3.0.0^2,4]undecane. Acidcatalyzed Cyclization Product of 6,7-Epoxyhumula-2,9-diene
  作者：Misuzu Namikawa、Tatsushi Murae、Takeyoshi Takahashi

  DOI：10.1246/bcsj.51.3616

  日期：1978.12

  6,7-Epoxyhumula-2,9-diene (2) was treated with 1.8 M sulfuric acid–acetone (1 : 1) to yield a new tricyclic diol, 5,9-dihydroxy-4,8,11,11-tetramethyltricyclo[6.3.0.02,4]undecane (9; diol B), together with tricyclohumuladiol (3; diol A), humulenol-II (4), a diol C (5b), a diol D (5a), and an acetonide (8a). The same reaction at 0° gave only 3. Tricyclohumuladiol (3) was shown to be a key intermediate in the reaction of 2 to form 4, 5a, 5b, 8a, and 9.

  6,7-环氧胡麻-2,9-二烯（2）用1.8 M硫酸-丙酮（1：1）处理，生成新的三环二醇5,9-二羟基-4,8,11,11-四甲基三环[6.3.0.02,4]十一烷（9；二醇B），以及三环胡麻二醇（3；二醇A）、胡麻烯醇-II（4）、二醇C（5b）、二醇D（5a）和乙酮（8a）。在0°时，同样的反应只生成3。三环胡麻二醇（3）是2反应形成4、5a、5b、8a和9的关键中间体。
• 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).
• Khomenko; Zenkovets; Barkhash, Russian Journal of Organic Chemistry, 1997, vol. 33, # 5, p. 595 - 600
  作者：Khomenko、Zenkovets、Barkhash

  DOI：——

  日期：——