(+)-(5S)-8,9-epoxy-10-hydroxycarvone | 1112055-51-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-(5S)-8,9-epoxy-10-hydroxycarvone
• 英文别名: (5S)-5-[2-(hydroxymethyl)oxiran-2-yl]-2-methylcyclohex-2-en-1-one
• CAS: 1112055-51-2
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: KCUIHGXGKBZLLY-PEHGTWAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苄基氯甲基醚 、 (+)-(5S)-8,9-epoxy-10-hydroxycarvone 在 四丁基碘化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 96.0h， 以62%的产率得到(5S)-2-methyl-5-[2-(phenylmethoxymethoxymethyl)oxiran-2-yl]cyclohex-2-en-1-one
  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：

  (S)-(+)-5-[1-(hydroxymethyl)vinyl]-2-methyl-cyclohex-2-enone 在 sodium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以60%的产率得到(+)-(5S)-8,9-epoxy-10-hydroxycarvone
  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).