2,6,6,9-tetramethyltricyclo<6.3.0.0^2,4>undecane-5,9-diol | 142722-68-7

• 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: 2,6,6,9-tetramethyltricyclo<6.3.0.0^2,4>undecane-5,9-diol
• 英文别名: (1aR,2S,4aR,5S,7aS,7bR)-3,3,5,7b-tetramethyl-1,1a,2,4,4a,6,7,7a-octahydrocyclopropa[e]azulene-2,5-diol
• CAS: 142722-68-7；142793-72-4
• 化学式: C₁₅H₂₆O₂
• 分子量: 238.37
• InChiKey: BFAVGMXYYRUDRR-XUGXRQAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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

• 作为反应物：
  描述：

  2,6,6,9-tetramethyltricyclo<6.3.0.0^2,4>undecane-5,9-diol 、 三甲基硅咪唑 在 吡啶 作用下， 反应 0.5h， 生成
  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

• New Sesquiterpenes from Edible Fungus<i>Clavicorona pyxidata</i>
  作者：Yong-Biao Zheng、Chun-Hua Lu、Zhong-Hui Zheng、Xin-Jian Lin、Wen-Jin Su、Yue-Mao Shen

  DOI：10.1002/hlca.200890235

  日期：2008.11

  Three new sesquiterpenes, pyxidatol A–C (1–3, resp.), were obtained from the fermentation culture of Clavaria pyxidata, together with two known ones, tsugicoline E (4) and omphadiol (5). Their structures were elucidated through spectroscopic analyses, including 1D- and 2D-NMR experiments, HR-ESI-Q-TOF mass spectrometry, chemical correlation, and X-ray single-crystal diffraction.

  三个新的倍半萜烯，pyxidatol A-C（1 - 3。，RESP），从发酵培养物中获得珊瑚菌pyxidata具有两个公知的物质，tsugicoline E（一起4）和omphadiol（5）。通过光谱分析，包括1D和2D-NMR实验，HR-ESI-Q-TOF质谱，化学相关性和X射线单晶衍射，阐明了它们的结构。
• Sesquiterpenes from the Basidiomycete <i>Omphalotus </i><i>i</i><i>lludens</i>
  作者：Trevor C. McMorris、Ricardo Lira、Peter K. Gantzel、Michael J. Kelner、Robin Dawe

  DOI：10.1021/np9904760

  日期：2000.11.1

  A new sesquiterpene, omphadiol (4), has been isolated from cultures of Omphalotus illudens. Several known compounds, including illudosin (1), were also obtained. Structures were determined using MS, NMR, and X-ray techniques.