青蒿素 M | 207446-90-0

• 物质功能分类: 天然产物 - 萜类
• 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
• 中文名称: 青蒿素 M
• 中文别名: 青蒿素M
• 英文名称: (-)-arteannuin M
• 英文别名: Arteannuin M；(3R,3aS,6R,6aS,9R,10R,10aS)-9,10-dihydroxy-3,6,9-trimethyl-3a,4,5,6,6a,7,8,10-octahydro-3H-benzo[h][1]benzofuran-2-one
• CAS: 207446-90-0
• 化学式: C₁₅H₂₄O₄
• 分子量: 268.353
• InChiKey: FONFQQKKCDVNRC-GZEPNZDPSA-N

物化性质

• 沸点：
  424.3±30.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-methoxytrifluoromethylphenylacetyl chloride 、 青蒿素 M 在 N,N-二异丙基乙胺 作用下， 以 吡啶 为溶剂， 以3%的产率得到(S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3R,3aS,6R,6aS,9R,10R,10aS)-9-hydroxy-3,6,9-trimethyl-2-oxo-decahydro-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-deoxyarteannuin B 在 四氧化锇 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 以58%的产率得到青蒿素 M
  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

文献信息

• Structure elucidation of arteannuin O, a novel cadinane diol from Artemisia annua, and the synthesis of arteannuins K, L, M and O
  作者：Lai-King Sy、Kung-Kai Cheung、Nian-Yong Zhu、Geoffrey D Brown

  DOI：10.1016/s0040-4020(01)00633-0

  日期：2001.10

  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.