[15-13CH3]-dihydro-epi-deoxyarteannuin B | 380487-60-5

• 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: [15-13CH3]-dihydro-epi-deoxyarteannuin B
• 英文别名: [15-13C]-dihydro-epi-deoxyarteannuin B；(3R,3aS,6R,6aS,10aS)-3,6-dimethyl-9-(113C)methyl-3,3a,4,5,6,6a,7,8-octahydrobenzo[h][1]benzofuran-2-one
• CAS: 380487-60-5
• 化学式: C₁₅H₂₂O₂
• 分子量: 235.327
• InChiKey: SXDUGGRDNCRRHY-KVNQZLKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [15-13CH3]-dihydro-epi-deoxyarteannuin B 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 生成
  参考文献：
  名称：

  Structure elucidation of arteannuin O, a novel cadinane diol from Artemisia annua, and the synthesis of arteannuins K, L, M and O

  摘要：

  The novel cadinane diol, arteannuin O (1), has been obtained from Artemisia annua and its structure has been established by 2D NMR and X-ray crystallography. A reconstructive synthesis of arteannuin O from artemisinin is described, which also yields the natural products arteannuin K and arteannuin L. Mechanistic considerations have led to the conclusion that the stereochemistry of the 5-hydroxyl group was wrongly assigned when arteannuins K, L and M were first reported as natural products. This was confirmed by derivatization of synthetic arteannuins K, L and M as their Mosher esters. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00633-0
• 作为产物：
  描述：

  青蒿素 在 barium dihydroxide 、 硫酸 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 13.67h， 生成 [15-13CH3]-dihydro-epi-deoxyarteannuin B
  参考文献：
  名称：

  二氢青蒿酸和二氢-的合成外延-deoxyarteannuin乙掺入稳定同位素标记的15位用于研究成青蒿素的生物合成

  摘要：

  [15- 13 c ^ 2 ^ h 3 ] -二氢青蒿酸（图3a）和[15- 13 CH 3 ]二氢外延-deoxyarteannuin B（图7b），用于评估在体内生物合成的前体青蒿素，已经从获得重建综合。青蒿素（1）的酸降解产生的十氢萘酮酸8用作常见的中间体：将标记的甲基格氏试剂添加到8中，可以通过改变所采用的后处理条件以高收率制备任何标记的前体。结果表明，两种化合物在储存时都易于自氧化，当用这些标记的前体在旨在确定青蒿中青蒿素生物合成途径的饲养实验中使用此类标记的前体时，这种氧化和随后的重排反应的产物可能与真正的代谢物混淆。

  DOI：

  10.1016/s0040-4020(01)00711-6

文献信息

• Syntheses of dihydroartemisinic acid and dihydro-epi-deoxyarteannuin B incorporating a stable isotope label at the 15-position for studies into the biosynthesis of artemisinin
  作者：Lai-King Sy、Nian-Yong Zhu、Geoffrey D Brown

  DOI：10.1016/s0040-4020(01)00711-6

  日期：2001.10

  [15-13C2H3]-Dihydroartemisinic acid (3a) and [15-13CH3]-dihydro-epi-deoxyarteannuin B (7b), intended for evaluation in vivo as biosynthetic precursors to artemisinin, have been obtained from a reconstructive synthesis. The decalenone acid 8 from acid degradation of artemisinin (1) serves as a common intermediate: following addition of labeled methyl Grignard reagent to 8, either labeled precursor can

  [15- 13 c ^ 2 ^ h 3 ] -二氢青蒿酸（图3a）和[15- 13 CH 3 ]二氢外延-deoxyarteannuin B（图7b），用于评估在体内生物合成的前体青蒿素，已经从获得重建综合。青蒿素（1）的酸降解产生的十氢萘酮酸8用作常见的中间体：将标记的甲基格氏试剂添加到8中，可以通过改变所采用的后处理条件以高收率制备任何标记的前体。结果表明，两种化合物在储存时都易于自氧化，当用这些标记的前体在旨在确定青蒿中青蒿素生物合成途径的饲养实验中使用此类标记的前体时，这种氧化和随后的重排反应的产物可能与真正的代谢物混淆。
• Structure elucidation of arteannuin O, a novel cadinane diol from Artemisia annua, and the synthesis of arteannuins K, L, M and O
  作者：Lai-King Sy、Kung-Kai Cheung、Nian-Yong Zhu、Geoffrey D Brown

  DOI：10.1016/s0040-4020(01)00633-0

  日期：2001.10

  The novel cadinane diol, arteannuin O (1), has been obtained from Artemisia annua and its structure has been established by 2D NMR and X-ray crystallography. A reconstructive synthesis of arteannuin O from artemisinin is described, which also yields the natural products arteannuin K and arteannuin L. Mechanistic considerations have led to the conclusion that the stereochemistry of the 5-hydroxyl group was wrongly assigned when arteannuins K, L and M were first reported as natural products. This was confirmed by derivatization of synthetic arteannuins K, L and M as their Mosher esters. (C) 2001 Elsevier Science Ltd. All rights reserved.