[2-[(1S)-4-methyl-5-oxocyclohex-3-en-1-yl]oxiran-2-yl]methyl 2,2-dimethylpropanoate | 1112055-59-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [2-[(1S)-4-methyl-5-oxocyclohex-3-en-1-yl]oxiran-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 1112055-59-0
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: RXEDCXHIRVVSRM-VPHXOMNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  55.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (+)-(5S)-8,9-epoxy-10-hydroxycarvone 、 三甲基乙酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以50%的产率得到[2-[(1S)-4-methyl-5-oxocyclohex-3-en-1-yl]oxiran-2-yl]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

文献信息

• Ti(III)-Promoted Radical Cyclization of Epoxy Enones. Total Synthesis of (+)-Paeonisuffrone
  作者：María Martín-Rodríguez、Raquel Galán-Fernández、Andrés Marcos-Escribano、Francisco A. Bermejo

  DOI：10.1021/jo8026033

  日期：2009.2.20

  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).