(3R,3aR,5aS,9bS)-3-hydroxy-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 | 157722-65-1

• 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,3aR,5aS,9bS)-3-hydroxy-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: 157722-65-1
• 化学式: C₁₇H₂₄O₃S₂
• 分子量: 340.508
• InChiKey: JRPVJPAOWLEWMA-SHPPOPEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  22.0
• 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：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3R,3aR,5aS,9bS)-3-hydroxy-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 phenyltrimethylammonium tribromide 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 1,4-二氧六环 、 水 、 乙腈 为溶剂， 反应 25.0h， 生成 2α-bromo-2,3-dihydro-11β-hydroxy-α-santonin
  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 、 氧气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 溶剂黄146 、 乙酸乙酯 、 苯 为溶剂， 反应 30.5h， 生成 (3R,3aR,5aS,9bS)-3-hydroxy-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

• 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.