(4R,4aR,7R,8S,8aS)-1-Methoxy-4,7-dimethyl-8-(3-oxo-butyl)-octahydro-isochromen-3-one

• 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: (4R,4aR,7R,8S,8aS)-1-Methoxy-4,7-dimethyl-8-(3-oxo-butyl)-octahydro-isochromen-3-one
• 英文别名: (4R,4aR,7R,8S,8aS)-1-methoxy-4,7-dimethyl-8-(3-oxobutyl)-1,4,4a,5,6,7,8,8a-octahydroisochromen-3-one
• 化学式: C₁₆H₂₆O₄
• 分子量: 282.38
• InChiKey: AJTGLQQHYIKGSG-DRSRYMOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甲醇 、 二氢青蒿酸 在 臭氧 作用下， 以 二氯甲烷 为溶剂， 以31%的产率得到(R)-2-[(1R,2S,3S,4R)-2-Formyl-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid
  参考文献：
  名称：

  The mechanism of the spontaneous autoxidation of dihydroartemisinic acid

  摘要：

  Dihydroartemisinic acid undergoes slow spontaneous autoxidation to artemisinin and other natural products, which have been reported from the medicinal plant Artemisia annua. The mechanism of this complex transformation is shown to involve four steps: (i) initial reaction of the Delta(4.5)-double bond of dihydroartemisinic acid with molecular oxygen, (ii) Hock cleavage of the resulting tertiary allylic hydroperoxide; (iii) oxygenation of the enol product from Hock cleavage; and (iv) cyclization of the resulting vicinal hydroperoxyl-aldehyde to the 1,2,4-trioxane system of artemisinin. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01193-0

文献信息

• The mechanism of the spontaneous autoxidation of dihydroartemisinic acid
  作者：Lai-King Sy、Geoffrey D Brown

  DOI：10.1016/s0040-4020(01)01193-0

  日期：2002.1

  Dihydroartemisinic acid undergoes slow spontaneous autoxidation to artemisinin and other natural products, which have been reported from the medicinal plant Artemisia annua. The mechanism of this complex transformation is shown to involve four steps: (i) initial reaction of the Delta(4.5)-double bond of dihydroartemisinic acid with molecular oxygen, (ii) Hock cleavage of the resulting tertiary allylic hydroperoxide; (iii) oxygenation of the enol product from Hock cleavage; and (iv) cyclization of the resulting vicinal hydroperoxyl-aldehyde to the 1,2,4-trioxane system of artemisinin. (C) 2002 Elsevier Science Ltd. All rights reserved.