(2R,4aS,6aS,7aR,8aS,10S,12aS,12bS,14aS,14bR)-methyl 10-acetoxy-12b-hydroxy-2,4a,6a,9,9,12a,14a-heptamethyl-7-oxodocosahydrobenzo[a]naphtho[2,1-f]azulene-2-carboxylate | 1417814-17-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4aS,6aS,7aR,8aS,10S,12aS,12bS,14aS,14bR)-methyl 10-acetoxy-12b-hydroxy-2,4a,6a,9,9,12a,14a-heptamethyl-7-oxodocosahydrobenzo[a]naphtho[2,1-f]azulene-2-carboxylate
• 英文别名: methyl (1S,3R,5S,7S,10S,11S,14S,15R,17R,20S)-7-acetyloxy-11-hydroxy-1,6,6,10,14,17,20-heptamethyl-2-oxopentacyclo[12.8.0.03,11.05,10.015,20]docosane-17-carboxylate
• CAS: 1417814-17-5
• 化学式: C₃₃H₅₂O₆
• 分子量: 544.772
• InChiKey: ZNHRTHGNACCOFX-BHRUQBRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  39
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,4aS,6aS,7aR,8aS,10S,12aS,12bS,14aS,14bR)-methyl 10-acetoxy-12b-hydroxy-2,4a,6a,9,9,12a,14a-heptamethyl-7-oxodocosahydrobenzo[a]naphtho[2,1-f]azulene-2-carboxylate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以53%的产率得到(2R,4aS,6aS,7aR,10S,12bR,14aS,14bR)-methyl 10-acetoxy-2,4a,6a,9,9,12b,14a-heptamethyl-7-oxo-1,2,3,4,4a,5,6,6a,7,7a,8,9,10,11,12,12b,13,14,14a,14b-icosahydrobenzo[a]naphtho[2,1-f]azulene-2-carboxylate
  参考文献：
  名称：

  Molecular Library Synthesis Using Complex Substrates: Expanding the Framework of Triterpenoids

  摘要：

  The remodeling of a natural product core framework by means of diversity-oriented synthesis (DOS) is a valuable approach to access diverse/biologically relevant chemical space and to overcome the limitations of combinatorial-type compounds. Here we provide proof of principle and a thorough conformational analysis for a general strategy whereby the inherent complexity of a starting material is used to define the regio- and stereochemical outcomes of reactions in chemical library construction. This is in contrast to the traditional DOS logic employing reaction development and catalysis to drive library diversity.

  DOI：

  10.1021/jo302211f
• 作为产物：
  描述：

  (2R,4aS,6aS,8aR,10S,12aS,14aS,14bR)-methyl 10-hydroxy-2,4a,6a,9,9,12a,14a-heptamethyl-1,2,3,4,4a,5,6,6a,7,8,8a,9,10,11,12,12a,13,14,14a,14b-icosahydropicene-2-carboxylate 在 四氢吡咯 、 吡啶 、 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 48.33h， 生成 (2R,4aS,6aS,6bR,8aS,10S,12aS,13aS,14aS,14bR)-methyl 10-acetoxy-6b-hydroxy-2,4a,6a,9,9,12a,14a-heptamethyl-13-oxodocosahydrobenzo[f]naphtho[2,1-a]azulene-2-carboxylate 、 (2R,4aS,6aS,7aR,8aS,10S,12aS,12bS,14aS,14bR)-methyl 10-acetoxy-12b-hydroxy-2,4a,6a,9,9,12a,14a-heptamethyl-7-oxodocosahydrobenzo[a]naphtho[2,1-f]azulene-2-carboxylate
  参考文献：
  名称：

  Molecular Library Synthesis Using Complex Substrates: Expanding the Framework of Triterpenoids

  摘要：

  The remodeling of a natural product core framework by means of diversity-oriented synthesis (DOS) is a valuable approach to access diverse/biologically relevant chemical space and to overcome the limitations of combinatorial-type compounds. Here we provide proof of principle and a thorough conformational analysis for a general strategy whereby the inherent complexity of a starting material is used to define the regio- and stereochemical outcomes of reactions in chemical library construction. This is in contrast to the traditional DOS logic employing reaction development and catalysis to drive library diversity.

  DOI：

  10.1021/jo302211f