methyl (2R)-2-[(1S,4R,4aS,7R)-7-[(2S,3R,6S)-1-formyl-6-[(2R)-1-methoxy-1-oxopropan-2-yl]-3-methyl-2-(3-oxobutyl)cyclohexyl]peroxy-4,7-dimethyl-2,3,4,4a,5,6-hexahydro-1H-naphthalen-1-yl]propanoate | 422565-48-8

• 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: methyl (2R)-2-[(1S,4R,4aS,7R)-7-[(2S,3R,6S)-1-formyl-6-[(2R)-1-methoxy-1-oxopropan-2-yl]-3-methyl-2-(3-oxobutyl)cyclohexyl]peroxy-4,7-dimethyl-2,3,4,4a,5,6-hexahydro-1H-naphthalen-1-yl]propanoate
• CAS: 422565-48-8
• 化学式: C₃₂H₅₀O₈
• 分子量: 562.744
• InChiKey: BPNWOJKANJTLPJ-WYMAHUGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (2R)-2-[(1S,4R,4aS,7R)-7-[(2S,3R,6S)-1-formyl-6-[(2R)-1-methoxy-1-oxopropan-2-yl]-3-methyl-2-(3-oxobutyl)cyclohexyl]peroxy-4,7-dimethyl-2,3,4,4a,5,6-hexahydro-1H-naphthalen-1-yl]propanoate 生成 methyl (2R)-2-[(3R,5aS,6R,9S,9aR)-9a-formyl-3-hydroxy-3,6-dimethyl-5,5a,6,7,8,9-hexahydro-4H-benzo[c]dioxepin-9-yl]propanoate 、 脱氧青蒿素 、 (R)-2-[(1S,3S,4R)-4-Methyl-2-oxo-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester 、 methyl (2R)-2-[(4R,4aS)-4,7-dimethyl-2,3,4,4a,5,6-hexahydronaphthalen-1-yl]propanoate
  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 氧气 、 氢气 作用下， 以 氘代氯仿 为溶剂， 反应 2556.75h， 生成 methyl (2R)-2-[(1S,4R,4aS,7R)-7-[(2S,3R,6S)-1-formyl-6-[(2R)-1-methoxy-1-oxopropan-2-yl]-3-methyl-2-(3-oxobutyl)cyclohexyl]peroxy-4,7-dimethyl-2,3,4,4a,5,6-hexahydro-1H-naphthalen-1-yl]propanoate
  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

文献信息

• 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.