(1S,2R,5R,6S,8S,9R,13S)-8-hydroxy-5,9,13-trimethyl-3,14-dioxatetracyclo[7.5.0.01,13.02,6]tetradecan-4-one | 138231-73-9

• 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: (1S,2R,5R,6S,8S,9R,13S)-8-hydroxy-5,9,13-trimethyl-3,14-dioxatetracyclo[7.5.0.01,13.02,6]tetradecan-4-one
• CAS: 138231-73-9
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: CMTSYTOHIWRTHG-XGRLGWONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2R,5R,6S,8S,9R,13S)-8-hydroxy-5,9,13-trimethyl-3,14-dioxatetracyclo[7.5.0.01,13.02,6]tetradecan-4-one 在 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以70%的产率得到(1S,2R,5R,6S,9S,13S)-5,9,13-trimethyl-3,14-dioxatetracyclo[7.5.0.01,13.02,6]tetradecane-4,8-dione
  参考文献：
  名称：

  Carbon-13 NMR spectroscopy of sesquiterpenes. 3. Synthesis and carbon-13 NMR spectral data of 4.alpha.,5.alpha.- and 4.beta.,5.beta.-epoxyeudesmanolides. Configuration and .gamma. effect of the oxirane ring

  摘要：

  The epoxide eudesmanolides 14-21, which constitute epimeric pairs with respect to the configuration of the oxirane ring, have been synthesized in a stereochemically unambiguous way. Comparison of their C-12 NMR spectra with those of the parent olefins 10-13 does not, however, reveal any significant correlation between the configuration of the oxirane ring and the shifts undergone by the signals of the gamma carbon atoms C-1/C-2/C-7/C-9/C-14.

  DOI：

  10.1021/jo00029a006
• 作为产物：
  描述：

  (1R,2S,4S,4aS)-2-((R)-2-Hydroxy-1-methyl-ethyl)-4a,8-dimethyl-4-triethylsilanyloxy-1,2,3,4,4a,5,6,7-octahydro-naphthalen-1-ol 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 、 溶剂黄146 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 10.0h， 生成 (1S,2R,5R,6S,8S,9R,13S)-8-hydroxy-5,9,13-trimethyl-3,14-dioxatetracyclo[7.5.0.01,13.02,6]tetradecan-4-one
  参考文献：
  名称：

  Carbon-13 NMR spectroscopy of sesquiterpenes. 3. Synthesis and carbon-13 NMR spectral data of 4.alpha.,5.alpha.- and 4.beta.,5.beta.-epoxyeudesmanolides. Configuration and .gamma. effect of the oxirane ring

  摘要：

  The epoxide eudesmanolides 14-21, which constitute epimeric pairs with respect to the configuration of the oxirane ring, have been synthesized in a stereochemically unambiguous way. Comparison of their C-12 NMR spectra with those of the parent olefins 10-13 does not, however, reveal any significant correlation between the configuration of the oxirane ring and the shifts undergone by the signals of the gamma carbon atoms C-1/C-2/C-7/C-9/C-14.

  DOI：

  10.1021/jo00029a006