(3R,3aS,5S,5aS,9bR)-3,5a,9-Trimethyl-5-triethylsilanyloxy-3a,4,5,5a,6,7,8,9b-octahydro-3H-naphtho[1,2-b]furan-2-one | 138091-17-5

• 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: (3R,3aS,5S,5aS,9bR)-3,5a,9-Trimethyl-5-triethylsilanyloxy-3a,4,5,5a,6,7,8,9b-octahydro-3H-naphtho[1,2-b]furan-2-one
• 英文别名: (3R,3aS,5S,5aS,9bR)-3,5a,9-trimethyl-5-triethylsilyloxy-3,3a,4,5,6,7,8,9b-octahydrobenzo[g][1]benzofuran-2-one
• CAS: 138091-17-5
• 化学式: C₂₁H₃₆O₃Si
• 分子量: 364.601
• InChiKey: GPPWCZLSVXURMF-BFDCFGGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.46
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,3aS,5S,5aS,9bR)-3,5a,9-Trimethyl-5-triethylsilanyloxy-3a,4,5,5a,6,7,8,9b-octahydro-3H-naphtho[1,2-b]furan-2-one 在 吡啶 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 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 26.0h， 生成 [(1S,2R,5R,6S,8S,9R,13S)-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
• 作为产物：
  描述：

  9-oxo-6α(H),7α(H)-eudesm-4(5),11(13)-dien-12,6-olide 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 (3R,3aS,5S,5aS,9bR)-3,5a,9-Trimethyl-5-triethylsilanyloxy-3a,4,5,5a,6,7,8,9b-octahydro-3H-naphtho[1,2-b]furan-2-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

文献信息

• 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
  作者：Miguel Carda、Juan F. Sanz、J. Alberto Marco

  DOI：10.1021/jo00029a006

  日期：1992.1

  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.