1-((1R,4R,4aS,8aR)-4,7-Dimethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-1-yl)-ethanone | 150408-50-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-((1R,4R,4aS,8aR)-4,7-Dimethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-1-yl)-ethanone
• 英文别名: 1-[(1R,4R,4aS,8aR)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]ethanone
• CAS: 150408-50-7
• 化学式: C₁₄H₂₂O
• 分子量: 206.328
• InChiKey: UOPSVPPZGCYXGJ-SAXRGWBVSA-N

物化性质

• 沸点：
  290.5±19.0 °C(Predicted)
• 密度：
  0.933±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-((1R,4R,4aS,8aR)-4,7-Dimethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-1-yl)-ethanone 在 氧气 、 三氟甲烷磺酸亚铜(I)苯联合体 (2:1) 、 rose bengal 作用下， 以 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 7.5h， 生成 peroxofabianane
  参考文献：
  名称：

  Conversion of Artemisinic Acid into (-)-Fabianane

  摘要：

  The conversion of (-)-fabianane from artemisinic acid was achieved in seven steps via photooxidative cyclization as a key step.

  DOI：

  10.3987/com-96-7419
• 作为产物：
  描述：

  dihydroartemisinic aldehyde 在 三乙烯二胺 、 2,2'-联吡啶 、 air 、 copper diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以44%的产率得到1-((1R,4R,4aS,8aR)-4,7-Dimethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-1-yl)-ethanone
  参考文献：
  名称：

  Conversion of Artemisinic Acid into (-)-Fabianane

  摘要：

  The conversion of (-)-fabianane from artemisinic acid was achieved in seven steps via photooxidative cyclization as a key step.

  DOI：

  10.3987/com-96-7419

文献信息

• The preparation of D-ring-contracted analogues of Qinghaosu (Artemisinin) from Qinghao (Artemisinic) acid and their In vitro activity against Plasmodium falciparum
  作者：Richard K Haynes、Simone C Vonwiller、Hong-Jie Wang

  DOI：10.1016/0040-4039(95)00806-n

  日期：1995.6

  Qinghao (Artemisinic) acid was converted into dihydroqinghao aldehyde and then submitted to copper(II)-catalysed oxidative deformylation. The resulting ketone was reduced to the diastereomeric alcohols which were submitted to photooxygenation, and then cleavage-oxygenation-cyclisation, catalysed by Cu(II)(OSO2CF3)(2), to give the title compounds. In vitro testing results for antimalarial activity indicated a remarkable dependence on the stereochemistry of the 9-methyl-substituent.
• Conversion of Artemisinic Acid into (-)-Fabianane
  作者：Mankil Jung、Byoung Hee Youn

  DOI：10.3987/com-96-7419

  日期：——

  The conversion of (-)-fabianane from artemisinic acid was achieved in seven steps via photooxidative cyclization as a key step.