青蒿素H | 207446-83-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环化合物
• 中文名称: 青蒿素H
• 英文名称: arteanniun H
• 英文别名: arteannuin H；(1R,4R,5S,9S,13R,14S)-4,13-dimethyl-8-methylidene-10,11-dioxatricyclo[7.4.1.05,14]tetradecan-12-one
• CAS: 207446-83-1
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: POIKAJZKFQOSJH-VUASIYQVSA-N

物化性质

• 沸点：
  318.6±35.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  青蒿素H 在 三苯基膦 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以4.5 mg的产率得到15-hydroxy-cadin-4-en-12-oic acid
  参考文献：
  名称：

  一种来自青蒿的新型内过氧化物和相关的倍半萜烯，可能源自烯丙基氢过氧化物

  摘要：

  七个新颖的卡丹烷倍半萜，包括七元内过氧化物内酯青蒿素H（1），两个六元内酯青蒿素I（4）和J（5），三个五元内酯青蒿素KM（6-8）和酮酸青蒿素N（9）已经被从干燥的叶中分离青蒿除了已知化合物二氢青蒿酸（27），双氢B（24）和二氢外延-deoxyarteannuin B（22）。提出这些新的倍半萜烯通过中间仲和叔烯丙基氢过氧化物与二氢青蒿酸生物遗传相关。

  DOI：

  10.1016/s0040-4020(98)00148-3
• 作为产物：
  描述：

  二氢青蒿酸 在 亚甲兰 作用下， 以 氘代氯仿 、 丙酮 为溶剂， 反应 672012.0h， 生成 青蒿素H
  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

• [EN] METHOD AND DEVICE FOR THE SYNTHESIS OF ARTEMISININ<br/>[FR] PROCÉDÉ ET DISPOSITIF POUR LA SYNTHÈSE D'ARTÉMISININE
  申请人：MAX PLANCK GESELLSCHAFT

  公开号：WO2013030247A1

  公开（公告）日：2013-03-07

  The present invention is directed to a method for producing artemisinin having the formula (6) from dihydroartennisinic acid in a continuous flow reactor using singlet oxygen as well as to the continuous flow reactor for producing artemisinin.

  本发明涉及一种使用单线态氧在连续流反应器中从二氢青蒿酸制备具有式（6）的青蒿素的方法，以及用于生产青蒿素的连续流反应器。
• METHOD AND DEVICE FOR THE SYNTHESIS OF ARTEMISININ
  申请人：Seeberger Peter H.

  公开号：US20140364630A1

  公开（公告）日：2014-12-11

  The present invention is directed to a method for producing artemisinin having the formula from dihydroartemisinic acid in a continuous flow reactor using singlet oxygen as well as to the continuous flow reactor for producing artemisinin.

  本发明涉及一种利用单线态氧从二氢青蒿酸中连续流反应器生产公式为的青蒿素的方法，以及用于生产青蒿素的连续流反应器。
• 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.
• 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.
• US9150535B2
  申请人：——

  公开号：US9150535B2

  公开（公告）日：2015-10-06