(8aS)-1,2,3,4,8,8a-hexahydro-7H-2,4a-ethanonaphthalen-7-one | 1192886-48-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (8aS)-1,2,3,4,8,8a-hexahydro-7H-2,4a-ethanonaphthalen-7-one
• 英文别名: (6S)-tricyclo[6.2.2.01,6]dodec-2-en-4-one
• CAS: 1192886-48-8
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: XMYQBGSKIOIQGZ-YZRBJQDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  (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
• 作为产物：
  描述：

  (2S)-2-(2-oxopropyl)bicyclo[2.2.2]octane-1-carboxaldehyde 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以54 mg的产率得到(8aS)-1,2,3,4,8,8a-hexahydro-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

• Amino acid salt catalyzed intramolecular Robinson annulation
  作者：Pingfan Li、Hisashi Yamamoto

  DOI：10.1039/b912325c

  日期：——

  The silica gel absorbed amino acid salt catalyzed asymmetric intramolecular Robinson annulation reaction has been developed; up to 97% ee was obtained with this readily recoverable organocatalyst.

  开发出了硅胶吸收氨基酸盐催化的不对称分子内罗宾逊环化反应；使用这种易于回收的有机催化剂，ee值高达 97%。
• 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.