12-epi-Teucvin | 89617-43-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 12-epi-Teucvin
• 英文别名: (1S,5'R,8S,9R,10R)-5'-(furan-3-yl)-10-methylspiro[2-oxatricyclo[6.3.1.04,12]dodec-4(12)-ene-9,3'-oxolane]-2',3-dione
• CAS: 89617-43-6
• 化学式: C₁₉H₂₀O₅
• 分子量: 328.365
• InChiKey: XJRMFKRYVTYFPN-MBMAUGEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 tris(triphenylphosphine)ruthenium(II) chloride 、 palladium on activated charcoal 、 氢气 、 氧气 、 lithium hydride 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 、 氯仿 、 乙酸乙酯 、 苯 为溶剂， 反应 168.0h， 生成 12-epi-Teucvin
  参考文献：
  名称：

  Efficient Installation and Elaboration of C4-C6 fused Furan Moiety in the Total Synthesis of Teucrium Clerodane Diterpenoids

  摘要：

  We previously reported the total synthesis of several Teucrium clerodane diterpenoids including teucvin (1), 12-epi-teucvin (2), montanin A (3) and teuscorolide (4) in a unified Diels-Alder approach. A full account for the tactical installation of the C4-C6 furan ring. of 3 from an alpha,beta-unsaturated lactone moiety, and the elaboration of the resulting furan unit into alpha,beta-unsaturated gamma-hydroxyl lactone for preparing 4 is discussed herein. In addition, the transformation of 3 and its 12-epimer into 1 and 2 by the air-mediated furan oxidation reaction is described.

  DOI：

  10.3987/com-14-13045

文献信息

• The Total Synthesis of Racemic Teucvin and 12-epi-Teucvin
  作者：Hsing-Jang Liu、Jia-Liang Zhu、I-Chia Chen、Renata Jankowska、Yongxin Han、Kak-Shan Shia

  DOI：10.1002/anie.200250681

  日期：2003.4.25
• Efficient Installation and Elaboration of C4-C6 fused Furan Moiety in the Total Synthesis of Teucrium Clerodane Diterpenoids
  作者：Jia-Liang Zhu、Hsing-Jang Liu、Yen-Ku Wu、I-Chia Chen

  DOI：10.3987/com-14-13045

  日期：——

  We previously reported the total synthesis of several Teucrium clerodane diterpenoids including teucvin (1), 12-epi-teucvin (2), montanin A (3) and teuscorolide (4) in a unified Diels-Alder approach. A full account for the tactical installation of the C4-C6 furan ring. of 3 from an alpha,beta-unsaturated lactone moiety, and the elaboration of the resulting furan unit into alpha,beta-unsaturated gamma-hydroxyl lactone for preparing 4 is discussed herein. In addition, the transformation of 3 and its 12-epimer into 1 and 2 by the air-mediated furan oxidation reaction is described.