(5S)-2-methyl-5-[2-(phenylmethoxymethoxymethyl)oxiran-2-yl]cyclohex-2-en-1-one | 1112055-52-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5S)-2-methyl-5-[2-(phenylmethoxymethoxymethyl)oxiran-2-yl]cyclohex-2-en-1-one
• CAS: 1112055-52-3
• 化学式: C₁₈H₂₂O₄
• 分子量: 302.37
• InChiKey: WFQRWNTVDYVGBY-ATNAJCNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  48.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5S)-2-methyl-5-[2-(phenylmethoxymethoxymethyl)oxiran-2-yl]cyclohex-2-en-1-one 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 20.0h， 以25%的产率得到(1R,5S,6S)-6-(hydroxymethyl)-2-methyl-6-(phenylmethoxymethoxymethyl)bicyclo[3.1.1]hept-2-en-1-ol
  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：

  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