(1S,2S,4aR,7R,8aR)-1-(3-((1S,2S,4S)-4-acetoxy-2-(carboxymethyl)-1,3,3-trimethylcyclohexyl)-2,3-dioxopropyl)-7-(methoxycarbonyl)-1,2,4a,7-tetramethyldecahydronaphthalene-2-carboxylic acid | 1417814-23-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S,2S,4aR,7R,8aR)-1-(3-((1S,2S,4S)-4-acetoxy-2-(carboxymethyl)-1,3,3-trimethylcyclohexyl)-2,3-dioxopropyl)-7-(methoxycarbonyl)-1,2,4a,7-tetramethyldecahydronaphthalene-2-carboxylic acid
• 英文别名: (1S,2S,4aR,7R,8aR)-1-[3-[(1S,2S,4S)-4-acetyloxy-2-(carboxymethyl)-1,3,3-trimethylcyclohexyl]-2,3-dioxopropyl]-7-methoxycarbonyl-1,2,4a,7-tetramethyl-3,4,5,6,8,8a-hexahydronaphthalene-2-carboxylic acid
• CAS: 1417814-23-3
• 化学式: C₃₃H₅₀O₁₀
• 分子量: 606.754
• InChiKey: PFDVNRRXPWGSSV-OUOSZNFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  43
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  161
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (1S,2S,4aR,7R,8aR)-1-(3-((1S,2S,4S)-4-acetoxy-2-(carboxymethyl)-1,3,3-trimethylcyclohexyl)-2,3-dioxopropyl)-7-(methoxycarbonyl)-1,2,4a,7-tetramethyldecahydronaphthalene-2-carboxylic acid 反应 0.25h， 以93%的产率得到(1S,2S,4aR,7R,8aR)-dimethyl 1-(3-((1S,2S,4S)-4-acetoxy-2-(2-methoxy-2-oxoethyl)-1,3,3-trimethylcyclohexyl)-2,3-dioxopropyl)-1,2,4a,7-tetramethyldecahydronaphthalene-2,7-dicarboxylate
  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-acetoxy-2,4a,6a,9,9,12a,14a-heptamethyl-7,13-dioxo-1,2,3,4,4a,5,6,6a,7,8,8a,9,10,11,12,12a,13,14,14a,14b-icosahydropicene-2-carboxylate 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 以18%的产率得到(2R,4aS,6aS,9aS,11S,13aS,16aS,16bR)-methyl 11-acetoxy-2,4a,6a,10,10,13a,16a-heptamethyl-7,8,14,15-tetraoxodocosahydrobenzo[6,7]cyclodeca[1,2-a]naphthalene-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