(2R)-2-[(1R,4R,4aS,8aS)-8-hydroperoxy-4-methyl-7-methylidene-2,3,4,4a,5,6,8,8a-octahydro-1H-naphthalen-1-yl]propanoic acid | 1372711-03-9

• 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: (2R)-2-[(1R,4R,4aS,8aS)-8-hydroperoxy-4-methyl-7-methylidene-2,3,4,4a,5,6,8,8a-octahydro-1H-naphthalen-1-yl]propanoic acid
• CAS: 1372711-03-9
• 化学式: C₁₅H₂₄O₄
• 分子量: 268.353
• InChiKey: PLAYIZSYWHFSJD-OOYFSQPHSA-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

• 作为产物：
  描述：

  二氢青蒿酸 在 氧气 、 tetraphenylporphyrin 作用下， 以 二氯甲烷 为溶剂， 生成 (2R)-2-[(1R,4R,4aS,8aS)-8-hydroperoxy-4-methyl-7-methylidene-2,3,4,4a,5,6,8,8a-octahydro-1H-naphthalen-1-yl]propanoic acid 、 4α-hydroperoxy-amorph-5-en-12-oic acid
  参考文献：
  名称：

  [EN] METHOD AND DEVICE FOR THE SYNTHESIS OF ARTEMISININ
  [FR] PROCÉDÉ ET DISPOSITIF POUR LA SYNTHÈSE D'ARTÉMISININE

  摘要：

  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。

  公开号：

  WO2013030247A1

文献信息

• [EN] METHOD AND APPARATUS FOR THE SYNTHESIS OF DIHYDROARTEMISININ AND ARTEMISININ DERIVATIVES<br/>[FR] PROCÉDÉ ET APPAREIL DE SYNTHÈSE DE DIHYDROARTÉMISININE ET DE DÉRIVÉS D'ARTÉMISININE
  申请人：MAX PLANCK GES ZUR FÖRDERUNG DER WISSENSCHAFTEN E V

  公开号：WO2015007693A1

  公开（公告）日：2015-01-22

  The present invention is directed to a method for continuous production of dihydroartemisinin and also artemisinin derivatives derived from dihydroartemisinin by using artemisinin or dihydroartemisinic acid (DHAA) as starting material as well as to a continuous flow reactor for producing dihydroartemisinin as well as the artemisinin derivatives. It was found that the reduction of artemisinin to dihydroartemisinin in a continuous process requires a special kind of reactor and a special combination of reagents comprising a hydride reducing agent, at least one activator such as an inorganic activator, at least one solid base, at least one aprotic solvent and at least one C1-C5 alcohol.

  本发明涉及一种连续生产二氢青蒿素以及由二氢青蒿素衍生的青蒿素衍生物的方法，该方法利用青蒿素或二氢青蒿酸（DHAA）作为起始物质，并且涉及一种用于生产二氢青蒿素以及青蒿素衍生物的连续流反应器。发现在连续过程中将青蒿素还原为二氢青蒿素需要一种特殊类型的反应器和一种特殊的试剂组合，包括一种氢化物还原剂，至少一种活化剂（例如无机活化剂），至少一种固体碱，至少一种无极性溶剂以及至少一种C1-C5醇。
• Method and device for the synthesis of artemisinin
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：EP2565197A1

  公开（公告）日：2013-03-06

  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.

  本发明涉及一种利用单线态氧在连续流反应器中从二氢青蒿素酸生产具有以下结构式的青蒿素的方法。
• Continuous-Flow Synthesis of the Anti-Malaria Drug Artemisinin
  作者：François Lévesque、Peter H. Seeberger

  DOI：10.1002/anie.201107446

  日期：2012.2.13

  Malaria is a serious global health issue. Artemisinin combination treatments are the first‐line drugs, but supplies are limited because artemisinin is obtained solely by extraction from Artemisia annua. A continuous‐flow process that converts dihydroartemisinic acid into artemisinin (see scheme) was shown to be an inexpensive and scalable process that can ensure a steady, affordable supply of artemisinin

  疟疾是一个严重的全球健康问题。青蒿素联合治疗是一线药物，但供应有限，因为青蒿素仅从青蒿中提取。将双氢青蒿酸转化为青蒿素的连续流动工艺（见方案）被证明是一种廉价且可扩展的工艺，可以确保稳定、负担得起的青蒿素供应。
• 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。
• METHOD AND APPARATUS FOR THE SYNTHESIS OF DIHYDROARTEMISININ AND ARTEMISININ DERIVATIVES
  申请人：MAX-PLANCK-GESELLSCHAFT ZUR FÖRDERUNG DER WISSENSCHAFTEN E.V.

  公开号：US20160145265A1

  公开（公告）日：2016-05-26

  The present invention is directed to a method for continuous production of dihydroartemisinin and also artemisinin derivatives derived from dihydroartemisinin by using artemisinin or dihydroartemisinic acid (DHAA) as starting material as well as to a continuous flow reactor for producing dihydroartemisinin as well as the artemisinin derivatives. It was found that the reduction of artemisinin to dihydroartemisinin in a continuous process requires a special kind of reactor and a special combination of reagents comprising a hydride reducing agent, at least one activator such as an inorganic activator, at least one solid base, at least one aprotic solvent and at least one C 1 -C 5 alcohol.

  本发明涉及一种用青蒿素或二氢青蒿酸（DHAA）作为起始材料连续生产二氢青蒿素和由二氢青蒿素衍生的青蒿素衍生物的方法，以及用于生产二氢青蒿素和青蒿素衍生物的连续流反应器。发现在连续过程中将青蒿素还原为二氢青蒿素需要一种特殊的反应器和一种特殊的试剂组合，包括一种氢化还原剂，至少一种活化剂，如无机活化剂，至少一种固体碱，至少一种无极溶剂和至少一种C1-C5醇。