1,1'-biphenyl-2-yl(4-nitrophenyl)methanone | 642044-05-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1,1'-biphenyl-2-yl(4-nitrophenyl)methanone
• 英文别名: (4-Nitrophenyl)-(2-phenylphenyl)methanone
• CAS: 642044-05-1
• 化学式: C₁₉H₁₃NO₃
• 分子量: 303.317
• InChiKey: DNSAZPLLBUSKSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,1'-biphenyl-2-yl(4-nitrophenyl)methanone 在 三氟甲磺酸 、 叠氮基三甲基硅烷 作用下， 以 三氟乙酸 为溶剂， 反应 12.0h， 以94%的产率得到6-(4-硝基苯基)菲啶
  参考文献：
  名称：

  Metal-Free Nitrogenation of 2-Acetylbiphenyls: Expeditious Synthesis of Phenanthridines

  摘要：

  An intermolecular nitrogenation reaction toward the synthesis of phenanthridines has been developed. This metal-free protocol provides a novel nitrogen-incorporation transformation using azides as the nitrogen source. Phenanthridines, which are of great interest in pharmaceutical and medicinal chemistry, are synthesized efficiently in one step. Moreover, the byproducts derived from the Schmidt reaction are inhibited, which further demonstrated the high chemoselectivity of this transformation.

  DOI：

  10.1021/acs.orglett.5b00797
• 作为产物：
  描述：

  2-联苯硼酸 、 4-硝基苯甲酰氯 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium phosphate monohydrate 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 1,1'-biphenyl-2-yl(4-nitrophenyl)methanone
  参考文献：
  名称：

  Metal-Free Nitrogenation of 2-Acetylbiphenyls: Expeditious Synthesis of Phenanthridines

  摘要：

  An intermolecular nitrogenation reaction toward the synthesis of phenanthridines has been developed. This metal-free protocol provides a novel nitrogen-incorporation transformation using azides as the nitrogen source. Phenanthridines, which are of great interest in pharmaceutical and medicinal chemistry, are synthesized efficiently in one step. Moreover, the byproducts derived from the Schmidt reaction are inhibited, which further demonstrated the high chemoselectivity of this transformation.

  DOI：

  10.1021/acs.orglett.5b00797

文献信息

• Synthesis and Structure−Activity Relationship of Aminobenzophenones. A Novel Class of p38 MAP Kinase Inhibitors with High Antiinflammatory Activity
  作者：Erik Rytter Ottosen、Morten Dahl Sørensen、Fredrik Björkling、Tine Skak-Nielsen、Marianne Scheel Fjording、Helle Aaes、Lise Binderup

  DOI：10.1021/jm030851s

  日期：2003.12.1

  We wish to report the synthesis and structure-activity relationship (SAR) of a series of 4-aminobenzophenones, as a novel compound class with high antiinflammatory activity. Our initial lead, 4-[(2-aminophenyl)amino]phenyl}(phenyl)methanone (3), was systematically optimized and resulted in compounds that potently inhibited the release of the proinflammatory cytokines IL-1beta and TNF-alpha in human peripheral blood mononuclear cells stimulated by LPS. One of the most potent compounds, among others, was 4-[(2-aminophenyl)amino]-2-chlorophenyl}(2-methylphenyl)methanone (45) with IC50 values of 14 and 6 nM for the inhibition of IL-1beta and TNF-alpha, respectively. Furthermore, we found these types of compounds to be potent and selective p38 MAP kinase inhibitors, e.g. 45 had an IC50 value of 10 nM. Molecular modeling was used to rationalize our SAR data and to propose a model for the interaction of compound 45 with the p38 MAP kinase. The model involved a favorable hydrogen bond between the carbonyl group of the benzophenone and the NH of Met-109, positioning ring A in the hydrophobic pocket I of the enzyme. Good antiinflammatory effects were demonstrated in two murine models of dermatitis after topical application (oxazolone and TPA model).
• Metal-Free Nitrogenation of 2-Acetylbiphenyls: Expeditious Synthesis of Phenanthridines
  作者：Conghui Tang、Yizhi Yuan、Ning Jiao

  DOI：10.1021/acs.orglett.5b00797

  日期：2015.5.1

  An intermolecular nitrogenation reaction toward the synthesis of phenanthridines has been developed. This metal-free protocol provides a novel nitrogen-incorporation transformation using azides as the nitrogen source. Phenanthridines, which are of great interest in pharmaceutical and medicinal chemistry, are synthesized efficiently in one step. Moreover, the byproducts derived from the Schmidt reaction are inhibited, which further demonstrated the high chemoselectivity of this transformation.