3-[[3-[(8S,8aR)-1,3,4,7,8,8a-hexahydro-8-methyl-7-oxo-2H-2,4a-ethanonaphthalen-8-yl]-1-oxopropyl]amino]-2,4-dihydroxybenzoic acid | 1195789-88-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[[3-[(8S,8aR)-1,3,4,7,8,8a-hexahydro-8-methyl-7-oxo-2H-2,4a-ethanonaphthalen-8-yl]-1-oxopropyl]amino]-2,4-dihydroxybenzoic acid
• 英文别名: (-)-nor-platencin；2,4-dihydroxy-3-[3-[(5S,6R)-5-methyl-4-oxo-5-tricyclo[6.2.2.01,6]dodec-2-enyl]propanoylamino]benzoic acid
• CAS: 1195789-88-8
• 化学式: C₂₃H₂₇NO₆
• 分子量: 413.47
• InChiKey: OBFLAGYWXPRHRJ-RJMAFRQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 3-[[3-[(8S,8aR)-1,3,4,7,8,8a-hexahydro-8-methyl-7-oxo-2H-2,4a-ethanonaphthalen-8-yl]-1-oxopropyl]amino]-2,4-dihydroxybenzoate 在 三(二甲氨基)锍二氟三甲基硅酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以56%的产率得到3-[[3-[(8S,8aR)-1,3,4,7,8,8a-hexahydro-8-methyl-7-oxo-2H-2,4a-ethanonaphthalen-8-yl]-1-oxopropyl]amino]-2,4-dihydroxybenzoic acid
  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.