4α-hydroperoxy-amorph-5-en-12-ol | 137288-63-2

• 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: 4α-hydroperoxy-amorph-5-en-12-ol
• 英文别名: (2R)-2-[(1S,4R,4aS,7R)-7-hydroperoxy-4,7-dimethyl-2,3,4,4a,5,6-hexahydro-1H-naphthalen-1-yl]propan-1-ol
• CAS: 137288-63-2
• 化学式: C₁₅H₂₆O₃
• 分子量: 254.37
• InChiKey: OWXJFPIGYIEVGZ-HYFYGGESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4α-hydroperoxy-amorph-5-en-12-ol 在 三氟乙酸 作用下， 以 氘代氯仿 为溶剂， 以3 mg的产率得到4-[(4R,4aS,7R,8S)-4,7-dimethyl-4,4a,5,6,7,8-hexahydro-3H-isochromen-8-yl]butan-2-one
  参考文献：
  名称：

  The role of the 12-carboxylic acid group in the spontaneous autoxidation of dihydroartemisinic acid

  摘要：

  Three of the four steps in the slow spontaneous autoxidation of dihydroartemisinic acid to artemisinin ('ene-type' reaction of molecular oxygen with the Delta(4.5) double bond, Hock cleavage of the resulting tertiary allylic hydroperoxide, oxygenation of the enol product from Hock cleavage and cyclization of the resulting vicinal hydroperoxyl-aldehyde to the 1,2,4-trioxane system of artemisinin) are shown to be assisted by the proximity of the 12-carboxylic acid functional group in dihydroartemisinic acid to the functional groups participating in these reactions. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01192-9
• 作为产物：
  描述：

  二氢青蒿酸 在 盐酸 、 lithium aluminium tetrahydride 、 亚甲兰 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 4.5h， 生成 4α-hydroperoxy-amorph-5-en-12-ol
  参考文献：
  名称：

  青蒿素h的仿生合成和烯丙基氢过氧化物的3,2-重排

  摘要：

  酰基内过氧化物青蒿素H，是最近报道的来自青蒿的一种新型天然产物，是从二氢青蒿酸的光氧化过程中分两个步骤制得的，从而证实了有关其衍生自仲烯丙基氢过氧化物的生物遗传学推测。还讨论了这种烯丙基氢过氧化物很少研究的3，2-重排反应。

  DOI：

  10.1016/s0040-4020(99)00987-4

文献信息

• Biomimetic synthesis of arteannuin h and the 3,2-rearrangement of allylic hydroperoxides
  作者：Lai-King Sy、Koon-Sin Ngo、Geoffrey D. Brown

  DOI：10.1016/s0040-4020(99)00987-4

  日期：1999.12

  The acyl endoperoxide arteannuin H, recently reported as a novel natural product from Artemtsia annua, has been obtained in two steps from the photooxidation of dihydroartemisinic acid, thereby confirming biogenetic speculation regarding its derivation from a secondary allylic hydroperoxide. The little studied 3,2-rearrangement reaction of such allylic hydroperoxides is also discussed.

  酰基内过氧化物青蒿素H，是最近报道的来自青蒿的一种新型天然产物，是从二氢青蒿酸的光氧化过程中分两个步骤制得的，从而证实了有关其衍生自仲烯丙基氢过氧化物的生物遗传学推测。还讨论了这种烯丙基氢过氧化物很少研究的3，2-重排反应。
• The role of the 12-carboxylic acid group in the spontaneous autoxidation of dihydroartemisinic acid
  作者：Lai-King Sy、Geoffrey D Brown

  DOI：10.1016/s0040-4020(01)01192-9

  日期：2002.1

  Three of the four steps in the slow spontaneous autoxidation of dihydroartemisinic acid to artemisinin ('ene-type' reaction of molecular oxygen with the Delta(4.5) double bond, Hock cleavage of the resulting tertiary allylic hydroperoxide, oxygenation of the enol product from Hock cleavage and cyclization of the resulting vicinal hydroperoxyl-aldehyde to the 1,2,4-trioxane system of artemisinin) are shown to be assisted by the proximity of the 12-carboxylic acid functional group in dihydroartemisinic acid to the functional groups participating in these reactions. (C) 2002 Elsevier Science Ltd. All rights reserved.