arteannuin K | 207446-88-6

• 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: arteannuin K
• 英文别名: (3R,3aS,6R,6aS,10R,10aS)-10-hydroxy-3,6,9-trimethyl-3,3a,4,5,6,6a,7,10-octahydrobenzo[h][1]benzofuran-2-one
• CAS: 207446-88-6
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: WHRODWCLNVCIKX-JZIIGSACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-methoxytrifluoromethylphenylacetyl chloride 、 arteannuin K 在 N,N-二异丙基乙胺 作用下， 以 吡啶 为溶剂， 以30%的产率得到(S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3R,3aS,6R,6aS,10R,10aS)-3,6,9-trimethyl-2-oxo-3,3a,4,5,6,6a,7,10-octahydro-2H-1-oxa-cyclopenta[d]naphthalen-10-yl ester
  参考文献：
  名称：

  Structure elucidation of arteannuin O, a novel cadinane diol from Artemisia annua, and the synthesis of arteannuins K, L, M and O

  摘要：

  The novel cadinane diol, arteannuin O (1), has been obtained from Artemisia annua and its structure has been established by 2D NMR and X-ray crystallography. A reconstructive synthesis of arteannuin O from artemisinin is described, which also yields the natural products arteannuin K and arteannuin L. Mechanistic considerations have led to the conclusion that the stereochemistry of the 5-hydroxyl group was wrongly assigned when arteannuins K, L and M were first reported as natural products. This was confirmed by derivatization of synthetic arteannuins K, L and M as their Mosher esters. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00633-0
• 作为产物：
  描述：

  dihydro-epi-arteanniun B 在 盐酸 作用下， 以 乙醚 为溶剂， 以79%的产率得到arteannuins K
  参考文献：
  名称：

  Structure elucidation of arteannuin O, a novel cadinane diol from Artemisia annua, and the synthesis of arteannuins K, L, M and O

  摘要：

  The novel cadinane diol, arteannuin O (1), has been obtained from Artemisia annua and its structure has been established by 2D NMR and X-ray crystallography. A reconstructive synthesis of arteannuin O from artemisinin is described, which also yields the natural products arteannuin K and arteannuin L. Mechanistic considerations have led to the conclusion that the stereochemistry of the 5-hydroxyl group was wrongly assigned when arteannuins K, L and M were first reported as natural products. This was confirmed by derivatization of synthetic arteannuins K, L and M as their Mosher esters. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00633-0