5α-hydroperoxy-amorph-4(15)-en-12-oic acid | 256647-94-6

• 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: 5α-hydroperoxy-amorph-4(15)-en-12-oic acid
• 英文别名: (2R)-2-[(1R,4R,4aS,8S,8aS)-8-hydroperoxy-4-methyl-7-methylidene-2,3,4,4a,5,6,8,8a-octahydro-1H-naphthalen-1-yl]propanoic acid
• CAS: 256647-94-6
• 化学式: C₁₅H₂₄O₄
• 分子量: 268.353
• InChiKey: PLAYIZSYWHFSJD-VUASIYQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  5α-hydroperoxy-amorph-4(15)-en-12-oic acid 以 氘代氯仿 为溶剂， 反应 672000.0h， 以1.6 mg的产率得到15-hydroperoxy-amorph-4-en-12-oic acid
  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
• 作为产物：
  描述：

  二氢青蒿酸 在 氧气 、 tetraphenylporphyrin 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到4α-hydroperoxy-amorph-5-en-12-oic acid
  参考文献：
  名称：

  A Continuous-Flow Process for the Synthesis of Artemisinin

  摘要：

  AbstractIsolation of the most effective antimalarial drug, artemisinin, from the plant sweet wormwood, does not yield sufficient quantities to provide the more than 300 million treatments needed each year. The high prices for the drug are a consequence of the unreliable and often insufficient supply of artemisinin. Large quantities of ineffective fake drugs find a market in Africa. Semisynthesis of artemisinin from inactive biological precursors, either dihydroartemisinic acid (DHAA) or artemisinic acid, offers a potentially attractive route to increase artemisinin production. Conversion of the plant waste product, DHAA, into artemisinin requires use of photochemically generated singlet oxygen at large scale. We met this challenge by developing a one‐pot photochemical continuous‐flow process for the semisynthesis of artemisinin from DHAA that yields 65 % product. Careful optimization resulted in a process characterized by short residence times. A method to extract DHAA from the mother liquor accumulated during commercial artemisinin extractions, a material that is currently discarded as waste, is also reported. The synthetic continuous‐flow process described here is an effective means to supplement the limited availability of artemisinin and ensure increased supplies of the drug for those in need.

  DOI：

  10.1002/chem.201204558

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。
• A Continuous-Flow Process for the Synthesis of Artemisinin
  作者：Daniel Kopetzki、François Lévesque、Peter H. Seeberger

  DOI：10.1002/chem.201204558

  日期：2013.4.22

  AbstractIsolation of the most effective antimalarial drug, artemisinin, from the plant sweet wormwood, does not yield sufficient quantities to provide the more than 300 million treatments needed each year. The high prices for the drug are a consequence of the unreliable and often insufficient supply of artemisinin. Large quantities of ineffective fake drugs find a market in Africa. Semisynthesis of artemisinin from inactive biological precursors, either dihydroartemisinic acid (DHAA) or artemisinic acid, offers a potentially attractive route to increase artemisinin production. Conversion of the plant waste product, DHAA, into artemisinin requires use of photochemically generated singlet oxygen at large scale. We met this challenge by developing a one‐pot photochemical continuous‐flow process for the semisynthesis of artemisinin from DHAA that yields 65 % product. Careful optimization resulted in a process characterized by short residence times. A method to extract DHAA from the mother liquor accumulated during commercial artemisinin extractions, a material that is currently discarded as waste, is also reported. The synthetic continuous‐flow process described here is an effective means to supplement the limited availability of artemisinin and ensure increased supplies of the drug for those in need.