(8S,8aS)-1,2,3,4,8,8a-hexahydro-8-methyl-7H-2,4a-ethanonaphthalen-7-one | 1195790-03-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (8S,8aS)-1,2,3,4,8,8a-hexahydro-8-methyl-7H-2,4a-ethanonaphthalen-7-one
• 英文别名: (5S,6S)-5-methyltricyclo[6.2.2.01,6]dodec-2-en-4-one
• CAS: 1195790-03-4
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: QBVCERFWALDVNV-URAGZPLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  (8S,8aS)-1,2,3,4,8,8a-hexahydro-8-methyl-7H-2,4a-ethanonaphthalen-7-one 、 丙烯酸甲酯（MA） 在 potassium tert-butylate 作用下， 以 乙醚 、 叔丁醇 为溶剂， 反应 0.58h， 以38.7%的产率得到methyl (8S,8aR)-1,3,4,7,8,8a-hexahydro-8-methyl-7-oxo-2H-2,4a-ethanonaphthalene-8-propanoate
  参考文献：
  名称：

  Synthesis and Antibacterial Properties of (−)-nor-Platencin

  摘要：

  An asymmetric Diels-Alder reaction between acrolein and 1-benzyloxymethyl-1,3-cyclohexadiene affords a bicyclic aldehyde that was elaborated in 11 steps to nor-platencin. nor-Platencin is 4-16 times less active than platencin against several resistant strains of Staphylococcus aureus, macrolide-resistant Enterococcus faecalis, and vancomycin-resistant Enterococcus faecium.

  DOI：

  10.1021/ol902194q
• 作为产物：
  描述：

  (8aS)-1,2,3,4,8,8a-hexahydro-7H-2,4a-ethanonaphthalen-7-one 、 碘甲烷 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 1.5h， 以75.8%的产率得到(8S,8aS)-1,2,3,4,8,8a-hexahydro-8-methyl-7H-2,4a-ethanonaphthalen-7-one
  参考文献：
  名称：

  Synthesis and Antibacterial Properties of (−)-nor-Platencin

  摘要：

  An asymmetric Diels-Alder reaction between acrolein and 1-benzyloxymethyl-1,3-cyclohexadiene affords a bicyclic aldehyde that was elaborated in 11 steps to nor-platencin. nor-Platencin is 4-16 times less active than platencin against several resistant strains of Staphylococcus aureus, macrolide-resistant Enterococcus faecalis, and vancomycin-resistant Enterococcus faecium.

  DOI：

  10.1021/ol902194q

文献信息

• Synthesis and Antibacterial Properties of (−)-<i>nor</i>-Platencin
  作者：Olga V. Barykina、Kerri L. Rossi、Michael J. Rybak、Barry B. Snider

  DOI：10.1021/ol902194q

  日期：2009.11.19

  An asymmetric Diels-Alder reaction between acrolein and 1-benzyloxymethyl-1,3-cyclohexadiene affords a bicyclic aldehyde that was elaborated in 11 steps to nor-platencin. nor-Platencin is 4-16 times less active than platencin against several resistant strains of Staphylococcus aureus, macrolide-resistant Enterococcus faecalis, and vancomycin-resistant Enterococcus faecium.