3,3-(1,2-Ethanediyldithio)-9β-hydroxy-(7αH,6,11βH)-eudesm-4-en-6,12-olide | 152715-93-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯嗪
• 英文名称: 3,3-(1,2-Ethanediyldithio)-9β-hydroxy-(7αH,6,11βH)-eudesm-4-en-6,12-olide
• 英文别名: (3'S,3'aS,5'S,5'aS,9'bS)-5'-hydroxy-3',5'a,9'-trimethylspiro[1,3-dithiolane-2,8'-3a,4,5,6,7,9b-hexahydro-3H-benzo[g][1]benzofuran]-2'-one
• CAS: 152715-93-0
• 化学式: C₁₇H₂₄O₃S₂
• 分子量: 340.508
• InChiKey: LYXONFZSKSKIRW-AEKDSLQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  97.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,3-(1,2-Ethanediyldithio)-9β-hydroxy-(7αH,6,11βH)-eudesm-4-en-6,12-olide 在 Raney Ni W-2 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以89%的产率得到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 Raney Ni W-2 甲基环氧丙烷 、 titanium(IV) isopropylate 、 sodium tetrahydroborate 、 三氟化硼乙醚 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 、 丙酮 为溶剂， 反应 44.5h， 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