2-(2-硝基苯氧基)-1-苯基丙烷-1-酮 | 70310-21-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-(2-硝基苯氧基)-1-苯基丙烷-1-酮
• 英文名称: 2-(2-nitrophenoxy)-1-phenylpropan-1-one
• 英文别名: 2-(2-nitro-phenoxy)-1-phenyl-propan-1-one；1-Propanone, 2-(2-nitrophenoxy)-1-phenyl-
• CAS: 70310-21-3
• 化学式: C₁₅H₁₃NO₄
• 分子量: 271.273
• InChiKey: UUJPYNYLJLAVMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-硝基苯氧基)-1-苯基丙烷-1-酮 在 palladium on activated charcoal sodium hypophosphite 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 2-methyl-3-phenyl-2H-benzo[1,4]oxazine
  参考文献：
  名称：

  A General Method for the Synthesis of 3-Phenyl-2H-1,4-benzoxazines and 3-Phenyl-2H-3,4-dihydro-1,4-benzoxazines

  摘要：

  DOI：

  10.1055/s-1979-28629
• 作为产物：
  描述：

  硝苯酚 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 16.0h， 以69%的产率得到2-(2-硝基苯氧基)-1-苯基丙烷-1-酮
  参考文献：
  名称：

  7-Oxo-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxamides as Selective CB₂ Cannabinoid Receptor Ligands: Structural Investigations around a Novel Class of Full Agonists

  摘要：

  Cannabinoid receptor agonists have gained attention as potential therapeutic targets of inflammatory and neuropathic pain. Here, we report the identification and optimization of a series of 7-oxo-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxamide derivatives as a novel chemotype of selective cannabinoid CB2 receptor agonists. Structural modifications led to the identification of several compounds as potent and selective cannabinoid receptor agonists (20, hCB(2) K-i = 2.5 nM, SI = 166; 21, hCB(2) K-i = 0.81 nM, SI = 383; 38, hCB(2) K-i = 15.8 nM, SI > 633; 56, hCB(2) K-i = 8.12 nM, SI > 1231; (R)-58, hCB(2) K-i = 9.24 nM, SI > 1082). The effect of a chiral center on the biological activity was also investigated, and it was found that the (R)-enantiomers exhibited greater affinity at the CB2 receptor than the (S)-enantiomers. In 3,5-cyclic adenosine monophosphate assays, the novel series behaved as agonists, exhibiting functional activity at the human CB2 receptor.

  DOI：

  10.1021/jm300763w

文献信息

• Ma; Zhang, Journal of Chemical Research - Part S, 2000, # 8, p. 388 - 389
  作者：Ma、Zhang

  DOI：——

  日期：——
• BATTISTONI P.; BRUNI P.; FAVA G., TETRAHEDRON, 1979, 35, NO 14. 1771-1775
  作者：BATTISTONI P.、 BRUNI P.、 FAVA G.

  DOI：——

  日期：——
• BATTISTONI P.; BRUNI P.; FAVA G., SYNTHESIS, 1979, NO 3, 220-221
  作者：BATTISTONI P.、 BRUNI P.、 FAVA G.

  DOI：——

  日期：——
• 7-Oxo-[1,4]oxazino[2,3,4-<i>ij</i>]quinoline-6-carboxamides as Selective CB₂ Cannabinoid Receptor Ligands: Structural Investigations around a Novel Class of Full Agonists
  作者：Pier Giovanni Baraldi、Giulia Saponaro、Allan R. Moorman、Romeo Romagnoli、Delia Preti、Stefania Baraldi、Emanuela Ruggiero、Katia Varani、Martina Targa、Fabrizio Vincenzi、Pier Andrea Borea、Mojgan Aghazadeh Tabrizi

  DOI：10.1021/jm300763w

  日期：2012.7.26

  Cannabinoid receptor agonists have gained attention as potential therapeutic targets of inflammatory and neuropathic pain. Here, we report the identification and optimization of a series of 7-oxo-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxamide derivatives as a novel chemotype of selective cannabinoid CB2 receptor agonists. Structural modifications led to the identification of several compounds as potent and selective cannabinoid receptor agonists (20, hCB(2) K-i = 2.5 nM, SI = 166; 21, hCB(2) K-i = 0.81 nM, SI = 383; 38, hCB(2) K-i = 15.8 nM, SI > 633; 56, hCB(2) K-i = 8.12 nM, SI > 1231; (R)-58, hCB(2) K-i = 9.24 nM, SI > 1082). The effect of a chiral center on the biological activity was also investigated, and it was found that the (R)-enantiomers exhibited greater affinity at the CB2 receptor than the (S)-enantiomers. In 3,5-cyclic adenosine monophosphate assays, the novel series behaved as agonists, exhibiting functional activity at the human CB2 receptor.
• A General Method for the Synthesis of 3-Phenyl-2<i>H</i>-1,4-benzoxazines and 3-Phenyl-2<i>H</i>-3,4-dihydro-1,4-benzoxazines
  作者：P. Battistoni、P. Bruni、G. Fava

  DOI：10.1055/s-1979-28629

  日期：——