[(1R,5S,6S)-1-hydroxy-6-(hydroxymethyl)-2-methyl-6-bicyclo[3.1.1]hept-2-enyl]methyl 2,2-dimethylpropanoate | 1112055-61-4

• 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: [(1R,5S,6S)-1-hydroxy-6-(hydroxymethyl)-2-methyl-6-bicyclo[3.1.1]hept-2-enyl]methyl 2,2-dimethylpropanoate
• CAS: 1112055-61-4
• 化学式: C₁₅H₂₄O₄
• 分子量: 268.353
• InChiKey: ZRWBZJHJUBGLBO-TUKIKUTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(1R,5S,6S)-1-hydroxy-6-(hydroxymethyl)-2-methyl-6-bicyclo[3.1.1]hept-2-enyl]methyl 2,2-dimethylpropanoate 、 苯甲醛二甲缩醛 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以80%的产率得到
  参考文献：
  名称：

  Ti(III)-Promoted Radical Cyclization of Epoxy Enones. Total Synthesis of (+)-Paeonisuffrone

  摘要：

  The total synthesis of (+)-paeonisuffrone starting from (+)-10-hydroxycarvone is described. The key step of our synthetic strategy is a titanium-catalyzed stereoselective cyclization initiated by epoxide opening through electron transfer. This reaction stereoselectively affords the highly oxygenated pinane skeleton present in the target molecule and opens a new and effective approach to the synthesis of the complex, biologically active terpenoids isolated from the roots of the Chinese paeony (Paeonia albiflora Pallas and Paeonia suffruticosa Andrews).

  DOI：

  10.1021/jo8026033
• 作为产物：
  描述：

  [2-[(1S)-4-methyl-5-oxocyclohex-3-en-1-yl]oxiran-2-yl]methyl 2,2-dimethylpropanoate 在 二氯二茂钛 、 锰 、 2,4,6-collidine hydrochloride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以46%的产率得到[(1R,5S,6S)-1-hydroxy-6-(hydroxymethyl)-2-methyl-6-bicyclo[3.1.1]hept-2-enyl]methyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  Ti(III)-Promoted Radical Cyclization of Epoxy Enones. Total Synthesis of (+)-Paeonisuffrone

  摘要：

  The total synthesis of (+)-paeonisuffrone starting from (+)-10-hydroxycarvone is described. The key step of our synthetic strategy is a titanium-catalyzed stereoselective cyclization initiated by epoxide opening through electron transfer. This reaction stereoselectively affords the highly oxygenated pinane skeleton present in the target molecule and opens a new and effective approach to the synthesis of the complex, biologically active terpenoids isolated from the roots of the Chinese paeony (Paeonia albiflora Pallas and Paeonia suffruticosa Andrews).

  DOI：

  10.1021/jo8026033