[(1R,2R,5R,6S,8S,9R,13R)-5,9,13-trimethyl-4-oxo-3,14-dioxatetracyclo[7.5.0.01,13.02,6]tetradecan-8-yl] acetate | 138091-20-0

• 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: [(1R,2R,5R,6S,8S,9R,13R)-5,9,13-trimethyl-4-oxo-3,14-dioxatetracyclo[7.5.0.01,13.02,6]tetradecan-8-yl] acetate
• CAS: 138091-20-0
• 化学式: C₁₇H₂₄O₅
• 分子量: 308.375
• InChiKey: GXHUETNKJKIKOP-VGIZTCKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  Acetic acid (3R,3aS,5S,5aS,9bR)-3,5a,9-trimethyl-2-oxo-2,3,3a,4,5,5a,6,7,8,9b-decahydro-naphtho[1,2-b]furan-5-yl ester 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以89%的产率得到[(1R,2R,5R,6S,8S,9R,13R)-5,9,13-trimethyl-4-oxo-3,14-dioxatetracyclo[7.5.0.01,13.02,6]tetradecan-8-yl] acetate
  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