dihydromethylartemisinate

• 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: dihydromethylartemisinate
• 英文别名: methyl dihydroartemisinate；dihydroartemisinic methyl ester；methyl 2-[(1R,4R,4aS,8aS)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]propanoate
• 化学式: C₁₆H₂₆O₂
• 分子量: 250.381
• InChiKey: PVZPMQOBBKNWQZ-VBBGFSMDSA-N

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：

  dihydromethylartemisinate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以100%的产率得到amorph-4-ene-12-ol
  参考文献：
  名称：

  质子和碳 13 核磁共振和一些紫杉烷（金好素衍生物）溶液中的构象

  摘要：

  报道了从巴西种植的青蒿中分离的青蒿素 I、II 和 V 以及合成衍生物青蒿素烯烃、酮和环氧树脂的总质子和碳 13 NMR 归属。这些化合物在溶液中的构象和构象平衡是从光谱数据和分子力学计算中获得的。

  DOI：

  10.1002/mrc.1260321004
• 作为产物：
  描述：

  methyl artemisinate 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 dihydromethylartemisinate
  参考文献：
  名称：

  质子和碳 13 核磁共振和一些紫杉烷（金好素衍生物）溶液中的构象

  摘要：

  报道了从巴西种植的青蒿中分离的青蒿素 I、II 和 V 以及合成衍生物青蒿素烯烃、酮和环氧树脂的总质子和碳 13 NMR 归属。这些化合物在溶液中的构象和构象平衡是从光谱数据和分子力学计算中获得的。

  DOI：

  10.1002/mrc.1260321004

文献信息

• CONVERSION OF AMORPHA-4,11-DIENE TO ARTEMISININ AND ARTEMISININ PRECURSORS
  申请人：Reiling Kinkead Keith

  公开号：US20060270863A1

  公开（公告）日：2006-11-30

  The present invention relates to methods for the conversion of amorpha-4,11-diene to artemisinin and various artemisinin precursors.

  本发明涉及将阿莫非-4,11-二烯转化为青蒿素和各种青蒿素前体的方法。
• Concise synthesis of artemisinin from a farnesyl diphosphate analogue
  作者：Xiaoping Tang、Melodi Demiray、Thomas Wirth、Rudolf K. Allemann

  DOI：10.1016/j.bmc.2017.03.068

  日期：2018.4

  many often-lengthy routes have been developed for its synthesis. Amorphadiene synthase, a key enzyme in the biosynthetic pathway of artemisinin, is able to convert an oxygenated farnesyl diphosphate analogue directly to dihydroartemisinic aldehyde, which can be converted to artemisinin in only four chemical steps, resulting in an efficient synthetic route to the anti-malaria drug.

  青蒿素是最有效的抗疟疾药物之一，并且已经开发了许多通常很长的合成路线。紫穗槐二烯合酶是青蒿素生物合成途径中的关键酶，能够将氧化法呢基二磷酸类似物直接转化为二氢青蒿醛，只需四个化学步骤即可将其转化为青蒿素，从而形成了抗疟疾药物的有效合成路线药品。
• Proton and carbon-13 NMR and conformation in solution of some amorphanes (quinghaosu derivatives)
  作者：Anita J. Marsaioli、Fred Y. Fujiwara、Mary Ann Foglio、Nikolai Sharapin、Jin-Sheng Zhang

  DOI：10.1002/mrc.1260321004

  日期：1994.10

  The total proton and carbon‐13 NMR assignments of quinghaosu I, II and V isolated from Artemisia annua cultivated in Brazil and of the synthetic derivatives quinghaosu alkene, ketone and epoxy are reported. The conformations and conformational equilibria of these compounds in solution were obtained from the spectral data and molecular mechanics calculations.

  报道了从巴西种植的青蒿中分离的青蒿素 I、II 和 V 以及合成衍生物青蒿素烯烃、酮和环氧树脂的总质子和碳 13 NMR 归属。这些化合物在溶液中的构象和构象平衡是从光谱数据和分子力学计算中获得的。
• A Practical and General Synthesis of (+)-Carboxyalkyldeoxoartemisinis
  作者：Mankil Jung、Antonio C. C. Freitas、James D. McChesney、Hala N. ElSohly

  DOI：10.3987/com-93-s(b)9

  日期：——

  Dye-sensitized photoxygenation of olefinic alcohols of dihydroartemisinates (4a-c) and direct oxidation of olefinic deoxoartemisinins (5a-c) have led to the preparation of carboxyalkyldeoxoartemisinins (6a-c), which are water-soluble and chemically more stable antimalarial agents.
• Amorpha-4,11-diene synthase catalyses the first probable step in artemisinin biosynthesis
  作者：Harro J. Bouwmeester、T.Eelco Wallaart、Michiel H.A. Janssen、Bert van Loo、Ben J.M. Jansen、Maarten A. Posthumus、Claus O. Schmidt、Jan-Willem De Kraker、Wilfried A. König、Maurice C.R. Franssen

  DOI：10.1016/s0031-9422(99)00206-x

  日期：1999.11

  The endoperoxide sesquiterpene lactone artemisinin and its derivatives are a promising new group of drugs against malaria. Artemisinin is a constituent of the annual herb Artemisia annua L. So far only the later steps in artemisinin biosynthesis - from artemisinic acid - have been elucidated and the expected olefinic sesquiterpene intermediate has never been demonstrated. In pentane extracts of A. annua leaves we detected a sesquiterpene with the mass spectrum of amorpha-4,11-diene. Synthesis of amorpha-4,11-diene from artemisinic acid confirmed the identity. In addition we identified several sesquiterpene synthases of which one of the major activities catalysed the formation of amorpha-4,11-diene from farnesyl diphosphate. This enzyme was partially purified and shows the typical characteristics of sesquiterpene syntheses, such as a broad pH optimum around 6.5-7.0, a molecular mass of 56 kDa, and a K-m of 0.6 mu M. The structure and configuration of amorpha-4,11-diene, its low content in A. annua and the high activity of amorpha-4,11-diene synthase all support that amorpha-4,11-diene is the likely olefinic sesquiterpene intermediate in the biosynthesis of artemisinin. (C) 1999 Elsevier Science Ltd. All rights reserved.