8β,9β-Epoxy-3-oxo-(7αH,6,11βH)-eudesm-4-en-6,12-olide | 144460-97-9

• 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: 8β,9β-Epoxy-3-oxo-(7αH,6,11βH)-eudesm-4-en-6,12-olide
• 英文别名: 8,9β-epoxy-3-oxo-7αH,6,11βH-eudesm-4-en-6,12-olide；(1S,2R,4S,5S,6S,9S)-1,6,11-trimethyl-3,8-dioxatetracyclo[8.4.0.02,4.05,9]tetradec-10-ene-7,12-dione
• CAS: 144460-97-9
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: JQHJLTHLJPQSJN-ZIOYAODRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• 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：

  8β,9β-Epoxy-3-oxo-(7αH,6,11βH)-eudesm-4-en-6,12-olide 在 Raney Ni W-2 titanium(IV) isopropylate 、 sodium tetrahydroborate 、 三氟化硼乙醚 、 溶剂黄146 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 35.5h， 生成 3,3-(1,2-Ethanediyldithio)-9β-hydroxy-(7αH,6,11βH)-eudesm-4-en-6,12-olide
  参考文献：
  名称：

  Synthesis of the reported structure of herbolide I and its C-11 epimer from artemisin

  摘要：

  Artemisin (1) was converted into 12 (the reported structure for herbolide I) and its C-11 epimer 19 via a synthetic pathway involving a functionality transfer from C-8 to C-9 and an A-ring refunctionalization. The H-1 and C-13 NMR data of synthetic products 12 and 19 reveal that the assigned structure of the natural herbolide I is erroneous.

  DOI：

  10.1021/jo00077a051
• 作为产物：
  描述：

  3-Oxo-(7αH,6,11βH)-eudesma-4,8-dien-6,12-olide 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 9.0h， 以99%的产率得到8β,9β-Epoxy-3-oxo-(7αH,6,11βH)-eudesm-4-en-6,12-olide
  参考文献：
  名称：

  Functionality transfer from C8 to C9 in sesquiterpenes. Synthesis of the named Herbolide E from artemisin.

  摘要：

  The key intermediate 6 was obtained in five steps from artemisin (1). The spectroscopic characteristics of the synthetic product 7a reveal that the proposed structure for the natural herbolide E must be revised.

  DOI：

  10.1016/s0040-4039(00)79147-7

文献信息

• Functionality transfer from C8 to C9 in sesquiterpenes. Synthesis of the named Herbolide E from artemisin.
  作者：Gonzalo Blay、Luz Cardona、Begoña García、José R. Pedro

  DOI：10.1016/s0040-4039(00)79147-7

  日期：1992.9

  The key intermediate 6 was obtained in five steps from artemisin (1). The spectroscopic characteristics of the synthetic product 7a reveal that the proposed structure for the natural herbolide E must be revised.
• Synthesis of the reported structure of herbolide I and its C-11 epimer from artemisin
  作者：Gonzalo Blay、Luz Cardona、Begona Garcia、Jose R. Pedro

  DOI：10.1021/jo00077a051

  日期：1993.12

  Artemisin (1) was converted into 12 (the reported structure for herbolide I) and its C-11 epimer 19 via a synthetic pathway involving a functionality transfer from C-8 to C-9 and an A-ring refunctionalization. The H-1 and C-13 NMR data of synthetic products 12 and 19 reveal that the assigned structure of the natural herbolide I is erroneous.
• Synthesis of 9-oxyfunctionalized eudesmanes from artemisin
  作者：Victoria Bargues、Gonzalo Blay、Begoña García、Cristina L. García、JoséR. Pedro

  DOI：10.1016/0040-4020(95)00221-s

  日期：1995.5

  Artemisin (1) was transformed into two natural sesquiterpenoids 2 and 3 in a sequence which involves functionality transfer from C-8 to C-9 and further elaboration of the A ring and the lactone moiety.