(3S,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,5,5a,6,7,9b-hexahydro-4H-spiro[naphtho[1,2-b]furan-8,2'-[1,3]dithiolan]-2(3H)-one | 20482-46-6

• 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: (3S,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,5,5a,6,7,9b-hexahydro-4H-spiro[naphtho[1,2-b]furan-8,2'-[1,3]dithiolan]-2(3H)-one
• CAS: 20482-46-6
• 化学式: C₁₇H₂₄O₂S₂
• 分子量: 324.508
• InChiKey: GKNGJVWFAHUJJW-ZAJUMQRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  21.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3S,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,5,5a,6,7,9b-hexahydro-4H-spiro[naphtho[1,2-b]furan-8,2'-[1,3]dithiolan]-2(3H)-one 在 镍 氢气 、 氧气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 3.5h， 生成 11,13-dihydro-11β-hydroxyarbusculin B
  参考文献：
  名称：

  Studies on the stereostructure of eudesmanolides from Umbelliferae: synthesis of 11β-angeloyloxy-α-santonin

  摘要：

  The first approach to the synthesis of decipienin A (1) having the stereostructure b (11 beta-angeloyloxy-alpha-santonin) have been performed following three different synthetic routes. The key step on the synthetic procedures is the stereoselective hydroxylation at C-11 position. An evaluation of the different used routes is discussed. Comparison of spectroscopic data of compound 1b and those from the natural decipienin A suggests that a stereostructure type a could be assigned to the natural product.

  DOI：

  10.1016/s0040-4020(01)80700-6
• 作为产物：
  描述：

  山道年 在 Wilkinson's catalyst 三氟化硼乙醚 、 氢气 作用下， 以 溶剂黄146 、 乙酸乙酯 、 苯 为溶剂， 反应 30.0h， 生成 (3S,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,5,5a,6,7,9b-hexahydro-4H-spiro[naphtho[1,2-b]furan-8,2'-[1,3]dithiolan]-2(3H)-one
  参考文献：
  名称：

  Studies on the stereostructure of eudesmanolides from Umbelliferae: synthesis of 11β-angeloyloxy-α-santonin

  摘要：

  The first approach to the synthesis of decipienin A (1) having the stereostructure b (11 beta-angeloyloxy-alpha-santonin) have been performed following three different synthetic routes. The key step on the synthetic procedures is the stereoselective hydroxylation at C-11 position. An evaluation of the different used routes is discussed. Comparison of spectroscopic data of compound 1b and those from the natural decipienin A suggests that a stereostructure type a could be assigned to the natural product.

  DOI：

  10.1016/s0040-4020(01)80700-6

文献信息

• Kutney, James P.; Singh, Ashok K., Canadian Journal of Chemistry, 1984, vol. 62, p. 2813 - 2817
  作者：Kutney, James P.、Singh, Ashok K.

  DOI：——

  日期：——
• Studies on the stereostructure of eudesmanolides from Umbelliferae: synthesis of 11β-angeloyloxy-α-santonin
  作者：Francisco A. Macías、José María Aguilar、José María G. Molinillo、Guillermo M. Massanet、Frank R. Fronczek

  DOI：10.1016/s0040-4020(01)80700-6

  日期：1994.5

  The first approach to the synthesis of decipienin A (1) having the stereostructure b (11 beta-angeloyloxy-alpha-santonin) have been performed following three different synthetic routes. The key step on the synthetic procedures is the stereoselective hydroxylation at C-11 position. An evaluation of the different used routes is discussed. Comparison of spectroscopic data of compound 1b and those from the natural decipienin A suggests that a stereostructure type a could be assigned to the natural product.