methyl (2R)-2-[(4R,4aS,8aS)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]propanoate | 85788-54-1

• 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-[(4R,4aS,8aS)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]propanoate
• CAS: 85788-54-1；87391-99-9；98575-64-5
• 化学式: C₁₆H₂₆O₂
• 分子量: 250.381
• InChiKey: PVZPMQOBBKNWQZ-YYJFMHSASA-N

物化性质

• 沸点：
  314.4±11.0 °C(Predicted)
• 密度：
  0.956±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl (2R)-2-[(4R,4aS,8aS)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]propanoate 生成 artemisinic acid
  参考文献：
  名称：

  On the conversion of dihydroartemisinic acid into artemisinin

  摘要：

  Mechanistic possibilities for the title conversion are discussed. By determining the oxygen 18-induced chemical shifts in the C-13 NMR spectrum of labeled 3, some of these mechanisms can be eliminated. Minor products obtained in the oxidative conversion of 2 into 3 have been identified.

  DOI：

  10.1021/jo00039a020

文献信息

• [EN] PROCESSES FOR THE PREPARATION OF ARTEMISININ AN ITS PRECURSORS<br/>[FR] PROCÉDÉ DE PRÉPARATION D'ARTÉMISININE ET DE SES PRÉCURSEURS
  申请人：AMYRIS BIOTECHNOLOGIES INC

  公开号：WO2009088404A1

  公开（公告）日：2009-07-16

  The present invention provides processes for the preparation of artemisinin and its precursors including amorphadiene, amorphadiene epoxide, dihydroartemisinic alcohol and dihydroartemisinic acid. Specifically, artemisinin is prepared by multi-step synthetic processes from amorphadiene, amorphadiene epoxide, dihydroartemisinic alcohol or dihydroartemisinic acid. Processes for the preparation of amorphadiene, amorphadiene epoxide, dihydroartemisinic alcohol and dihydroartemisinic acid are also disclosed.

  本发明提供了制备青蒿素及其前体的方法，包括阿莫菲二烯、阿莫菲二烯环氧化物、二氢青蒿醇和二氢青蒿酸。具体来说，青蒿素通过从阿莫菲二烯、阿莫菲二烯环氧化物、二氢青蒿醇或二氢青蒿酸进行多步合成过程而制备。还公开了制备阿莫菲二烯、阿莫菲二烯环氧化物、二氢青蒿醇和二氢青蒿酸的方法。
• On the conversion of dihydroartemisinic acid into artemisinin
  作者：Nancy Acton、Ronald J. Roth

  DOI：10.1021/jo00039a020

  日期：1992.6

  Mechanistic possibilities for the title conversion are discussed. By determining the oxygen 18-induced chemical shifts in the C-13 NMR spectrum of labeled 3, some of these mechanisms can be eliminated. Minor products obtained in the oxidative conversion of 2 into 3 have been identified.