(1S,3R,3aS,5aR,9aS,9bS)-3-hydroxy-1-[[6-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]methyl]-1,2,3,3a,4,5a,6,7,8,9,9a,9b-dodecahydrocyclopenta[a]naphthalen-5-one | 1188988-76-2

• 分子结构分类: 有机化合物
• 英文名称: (1S,3R,3aS,5aR,9aS,9bS)-3-hydroxy-1-[[6-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]methyl]-1,2,3,3a,4,5a,6,7,8,9,9a,9b-dodecahydrocyclopenta[a]naphthalen-5-one
• CAS: 1188988-76-2
• 化学式: C₂₆H₃₈BNO₅
• 分子量: 455.402
• InChiKey: SXVNHDDCTARGFL-BHEIXRHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  77.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,3R,3aS,5aR,9aS,9bS)-3-hydroxy-1-[[6-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]methyl]-1,2,3,3a,4,5a,6,7,8,9,9a,9b-dodecahydrocyclopenta[a]naphthalen-5-one 在 邻苯二甲酸二甲酯 、 silica gel 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到(1S,3aR,5aR,9aS,9bS)-1-[[6-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]methyl]-2,3a,4,5a,6,7,8,9,9a,9b-decahydro-1H-cyclopenta[a]naphthalene-3,5-dione
  参考文献：
  名称：

  Total Synthesis of Alkaloid (±)-G. B. 13 Using a Rh(I)-Catalyzed Ketone Hydroarylation and Late-Stage Pyridine Reduction

  摘要：

  Total synthesis of the Galbulimima alkaloid G. B. 13 was achieved utilizing a functionalized pyridine moiety as a piperidine surrogate. Key to the success of the synthesis was the development of an unprecedented rhodium-catalyzed 1,2-addition of an arylboronic ester into an unactivated ketone.

  DOI：

  10.1021/ja9063487
• 作为产物：
  描述：

  联硼酸频那醇酯 、 (1S,3R,3aS,5aR,9aS,9bS)-1-[(3-bromo-6-methoxypyridin-2-yl)methyl]-3-hydroxy-1,2,3,3a,4,5a,6,7,8,9,9a,9b-dodecahydrocyclopenta[a]naphthalen-5-one 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 potassium acetate 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以65%的产率得到(1S,3R,3aS,5aR,9aS,9bS)-3-hydroxy-1-[[6-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]methyl]-1,2,3,3a,4,5a,6,7,8,9,9a,9b-dodecahydrocyclopenta[a]naphthalen-5-one
  参考文献：
  名称：

  Total Synthesis of Alkaloid (±)-G. B. 13 Using a Rh(I)-Catalyzed Ketone Hydroarylation and Late-Stage Pyridine Reduction

  摘要：

  Total synthesis of the Galbulimima alkaloid G. B. 13 was achieved utilizing a functionalized pyridine moiety as a piperidine surrogate. Key to the success of the synthesis was the development of an unprecedented rhodium-catalyzed 1,2-addition of an arylboronic ester into an unactivated ketone.

  DOI：

  10.1021/ja9063487