(+/-)-(1S*,3S*,4R*,5S*,7R*,8R*,9S*,11S*,13R*)-3,4,5,7-Tetrachlor-11-isopropyl-1,6,6-trimethoxy-8-methyl-2,12-dioxapentacyclo<6.5.0.0^3,7.0^5,9.0^11,13>dodecan-10-on

• 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: (+/-)-(1S*,3S*,4R*,5S*,7R*,8R*,9S*,11S*,13R*)-3,4,5,7-Tetrachlor-11-isopropyl-1,6,6-trimethoxy-8-methyl-2,12-dioxapentacyclo<6.5.0.0^3,7.0^5,9.0^11,13>dodecan-10-on
• 英文别名: (+/-)-(1S*,3S*,4R*,5S*,7R*,8R*,9S*,11S*,13R*)-3,4,5,7-Tetrachlor-11-isopropyl-1,6,6-trimethoxy-8-methyl-2,12-dioxapentacyclo[6.5.0.0^3,7.0^5,9.0^11,13]dodecan-10-on；(1R,2R,4S,5R,6S,8R,9R,11S,13S)-2,4,5,6-tetrachloro-3,3,8-trimethoxy-1-methyl-11-propan-2-yl-7,10-dioxapentacyclo[6.5.0.02,6.04,13.09,11]tridecan-12-one
• 化学式: C₁₈H₂₂Cl₄O₆
• 分子量: 476.181
• InChiKey: SDXJKSBMPVTDJZ-PITVLYOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  百里醌 在 air 、 sodium 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 125.5h， 生成 (+/-)-(1S*,3S*,4R*,5S*,7R*,8R*,9S*,11S*,13R*)-3,4,5,7-Tetrachlor-11-isopropyl-1,6,6-trimethoxy-8-methyl-2,12-dioxapentacyclo<6.5.0.0^3,7.0^5,9.0^11,13>dodecan-10-on
  参考文献：
  名称：

  Versuche zur enantiomerenreinen Synthese des Chatancins, 1. Mitt. Synthese von (1R,2S,6S,7R,8S,3?S)-2-(4?-Benzyloxy-3?-methylbutoyl)-7-hydroxy-8-isopropyl-1-methylbicyclo [4.4.0]decan-4-on

  摘要：

  Our first target on the way towards the synthesis of enantiomerically pure chatancin is the preparation of the title compound. The cycloadduct of 5,5-dimethoxy- 1,2,3,4-tetrachlorocyclopentadiene and thymoquinone is stereo- and regioselectively reduced to the tricyclic ketoalcohol 4, which by nucleophilic cyclisation and reductive removal of the keto group as well as the chlorine atoms yielded a tetracyclic dimethoxyketal. Acidic hydrolysis freed the keto group, which now was treated with a chiral lithium alkyl compound derived from methyl (R)-2-methyl-3-hydroxypropionate in few steps. The resulting stereomeric tertiary alkohols were fragmented and the decalinones thus obtained separated. X-ray analysis permitted the determination of the absolute configuration of these decalinone derivatives.

  DOI：

  10.1007/bf00812715

文献信息

• Versuche zur enantiomerenreinen Synthese des Chatancins, 1. Mitt. Synthese von (1R,2S,6S,7R,8S,3?S)-2-(4?-Benzyloxy-3?-methylbutoyl)-7-hydroxy-8-isopropyl-1-methylbicyclo [4.4.0]decan-4-on
  作者：W. D. Aichberger、J. Aigner、E. G�ssinger、K. Gruber、G. Menz

  DOI：10.1007/bf00812715

  日期：——

  Our first target on the way towards the synthesis of enantiomerically pure chatancin is the preparation of the title compound. The cycloadduct of 5,5-dimethoxy- 1,2,3,4-tetrachlorocyclopentadiene and thymoquinone is stereo- and regioselectively reduced to the tricyclic ketoalcohol 4, which by nucleophilic cyclisation and reductive removal of the keto group as well as the chlorine atoms yielded a tetracyclic dimethoxyketal. Acidic hydrolysis freed the keto group, which now was treated with a chiral lithium alkyl compound derived from methyl (R)-2-methyl-3-hydroxypropionate in few steps. The resulting stereomeric tertiary alkohols were fragmented and the decalinones thus obtained separated. X-ray analysis permitted the determination of the absolute configuration of these decalinone derivatives.