Trifluoro-methanesulfonic acid (3S,3aS,4S,5aR,9bS)-3,5a,9-trimethyl-2,8-dioxo-2,3,3a,4,5,5a,6,7,8,9b-decahydro-naphtho[1,2-b]furan-4-yl ester | 144461-01-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: Trifluoro-methanesulfonic acid (3S,3aS,4S,5aR,9bS)-3,5a,9-trimethyl-2,8-dioxo-2,3,3a,4,5,5a,6,7,8,9b-decahydro-naphtho[1,2-b]furan-4-yl ester
• CAS: 144461-01-8
• 化学式: C₁₆H₁₉F₃O₆S
• 分子量: 396.384
• InChiKey: IZABPOIMNVNRID-DBIGVJDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  86.74
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonic acid (3S,3aS,4S,5aR,9bS)-3,5a,9-trimethyl-2,8-dioxo-2,3,3a,4,5,5a,6,7,8,9b-decahydro-naphtho[1,2-b]furan-4-yl ester 在 lithium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 0.5h， 生成 3-Oxo-(7αH,6,11βH)-eudesma-4,8-dien-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
• 作为产物：
  描述：

  蒿素; 苦艾内酯 在 Wilkinson's catalyst 吡啶 、 氢气 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 0.5h， 生成 Trifluoro-methanesulfonic acid (3S,3aS,4S,5aR,9bS)-3,5a,9-trimethyl-2,8-dioxo-2,3,3a,4,5,5a,6,7,8,9b-decahydro-naphtho[1,2-b]furan-4-yl ester
  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

• 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.