(R)-methyl 4-((3aS,3bS,5aS,7S,9aS,10aR,11aR)-7-acetoxy-3a,3b,6,6,9a-pentamethyl-10-oxo-3a,3b,4,5,5a,6,7,8,9,9a,10,10a,11,11a-tetradecahydro-3H-benzo[f ]cyclopenta[a]-azulen-1-yl)pentanoate | 1486488-38-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (R)-methyl 4-((3aS,3bS,5aS,7S,9aS,10aR,11aR)-7-acetoxy-3a,3b,6,6,9a-pentamethyl-10-oxo-3a,3b,4,5,5a,6,7,8,9,9a,10,10a,11,11a-tetradecahydro-3H-benzo[f ]cyclopenta[a]-azulen-1-yl)pentanoate
• 英文别名: methyl (4R)-4-[(1R,3S,6S,8S,11S,12S,16R)-6-acetyloxy-3,7,7,11,12-pentamethyl-2-oxo-15-tetracyclo[9.6.0.03,8.012,16]heptadec-14-enyl]pentanoate
• CAS: 1486488-38-3
• 化学式: C₃₀H₄₆O₅
• 分子量: 486.692
• InChiKey: CSBIWXIVFBMXHN-FMHQGCPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (R)-methyl 4-((1R,3aR,6aS,8S,10aS,13aR)-8-acetoxy-3a,7,7,10a,13a-pentamethyl-4,11-dioxohexadecahydro-1H-benzo[a]cyclopenta[f ][10]annulen-1-yl)pentanoate 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以10%的产率得到(R)-methyl 4-((1R,3bS,5aS,7S,9aS,10aR,11aR)-7-acetoxy-3b,6,6,9a,11a-pentamethyl-10-oxo-2,3b,4,5,5a,6,7,8,9,9a,10,10a,11,11a-tetradecahydro-1H-benzo[f ]cyclopenta[a]-azulen-1-yl)pentanoate
  参考文献：
  名称：

  Direct Access to 6/5/7/5- and 6/7/5/5-Fused Tetracyclic Triterpenoids via Divergent Transannular Aldol Reaction of Lanosterol-Derived Diketone

  摘要：

  In an effort to access biologically relevant chemical space, a complex natural product derived nonsymmetrical diketone was prepared as a substrate for divergent transannular aldol reactions. The use of common aldol conditions resulted in predominant syn-addition via pathway a, while the use of alumina provided access to the anti-adduct. Screening of a range of Lewis acids of varying strength unexpectedly resulted in the formation of aldol products with 6/7/5/5-fused molecular skeleton via pathway b.

  DOI：

  10.1021/jo402005b