(+/-)-6,9-desmethylartemisinin | 119297-26-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (+/-)-6,9-desmethylartemisinin
• 英文别名: (+/-)-6,9-desdimethylqinghaosu；(1R,4R,8S,12S,13R)-1-methyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one
• CAS: 119297-26-6
• 化学式: C₁₃H₁₈O₅
• 分子量: 254.283
• InChiKey: NGQPRIKIGQHDJB-NJIBTWPXSA-N

物化性质

• 熔点：
  130.0-135 °C
• 沸点：
  381.0±42.0 °C(predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (3aRS,6aSR,9RS,9aSR,9bRS)-9a-hydroxy-9-methyl-2,3,3a,6,6a,7,8,9,9a,9b-decahydro-1-oxa-1H-phenalene 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 、 铬酸 作用下， 以 甲醇 、 乙醚 、 乙酸乙酯 、 丙酮 为溶剂， 反应 6.5h， 生成 (+/-)-6,9-desmethylartemisinin
  参考文献：
  名称：

  Preparation of a Bicyclic Analog of Qinghao (Artemisinic) Acid via a Lewis Acid Catalyzed Ionic Diels-Alder Reaction Involving a Hydroxy Diene and Cyclic Enone and Facile Conversion into (.+-.)-6,9-Desdimethylqinghaosu

  摘要：

  Treatment of 6-methylcyclohex-2-enone (8) and hexa-3,5-dien-1-ol (14) either in dichloromethane at -20 to 0 degrees C with aluminum chloride (1 equiv) or in acetonitrile at -20 degrees C with Cu(II) trifluoromethanesulfonate (1 equiv) rapidly provides in a highly stereoselective reaction the hemiacetal Diels-Aider adduct 15, which with a trans ring junction and anti methyl group is considered to arise via an ionic Gassman-type Diels-Alder reaction involving prior formation of a hemiacetal between the alcohol and enone followed by generation of an allylic cation from the hemiacetal mediated by the Lewis acid. The adduct 15 is then converted in straightforward fashion into the methyl ester of the desdimethyl analogue of qinghao (artemisinic) acid, which upon sequential photosensitized oxygenation and then Fe(phen)(3)(PF6)(3)/copper(II) triflate catalyzed cleavage-oxygenation provides (+/-)-6,9-desdimethylqinghaosu.

  DOI：

  10.1021/jo00096a015

文献信息

• Simplified analogs of the antimalarial artemisinin: synthesis of 6,9-desmethylartemisinin
  作者：Mitchell A. Avery、Clive Jennings-White、Wesley K. M. Chong

  DOI：10.1021/jo00269a009

  日期：1989.4
• AVERY, MITCHELL A.;JENNINGS-WHITE, CLIVE;CHONG, WESLEY K. M., J. ORG. CHEM., 54,(1989) N, C. 1792-1795
  作者：AVERY, MITCHELL A.、JENNINGS-WHITE, CLIVE、CHONG, WESLEY K. M.

  DOI：——

  日期：——