N-(3-溴吡啶-2-基)苯甲酰胺 | 620939-76-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(3-溴吡啶-2-基)苯甲酰胺
• 英文名称: N-(3-bromopyridin-2-yl)-2-benzamide
• 英文别名: N-(3-bromopyridin-2-yl)benzamide
• CAS: 620939-76-6
• 化学式: C₁₂H₉BrN₂O
• 分子量: 277.12
• InChiKey: SZRQLPAPAINFKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  N-(3-溴吡啶-2-基)苯甲酰胺 在 sodium amide 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 为溶剂， 反应 7.0h， 生成 2-phenyl[1,3]oxazolo[4,5-b]pyridine
  参考文献：
  名称：

  New Access to Oxazolopyridines via Hydroxyamidine Derivatives; Application to Quinolines

  摘要：

  通过在二甲基乙酰胺中加热，从齐聚物或羟基脒衍生物中高产合成了几种 2-芳基和 2-杂芳基恶唑并[4,5-b]吡啶。这些中间体是通过与络合碱 NaNH2-t-BuONa （5:2）发生热反应生成的。喹啉衍生物也可以发生同样的反应。

  DOI：

  10.1055/s-2003-41052
• 作为产物：
  描述：

  2-氨基-3-溴吡啶 、 苯甲酰氯 以 吡啶 为溶剂， 反应 1.0h， 以88%的产率得到N-(3-溴吡啶-2-基)苯甲酰胺
  参考文献：
  名称：

  New Access to Oxazolopyridines via Hydroxyamidine Derivatives; Application to Quinolines

  摘要：

  通过在二甲基乙酰胺中加热，从齐聚物或羟基脒衍生物中高产合成了几种 2-芳基和 2-杂芳基恶唑并[4,5-b]吡啶。这些中间体是通过与络合碱 NaNH2-t-BuONa （5:2）发生热反应生成的。喹啉衍生物也可以发生同样的反应。

  DOI：

  10.1055/s-2003-41052

文献信息

• Development of <i>N</i>-Methyl-(2-arylquinolin-4-yl)oxypropanamides as Leads to PET Radioligands for Translocator Protein (18 kDa)
  作者：Chad Brouwer、Kimberly Jenko、Sami S. Zoghbi、Robert B. Innis、Victor W. Pike

  DOI：10.1021/jm5007947

  日期：2014.7.24

  Translocator protein (18 kDa), known as TSPO, is a recognized biomarker of neuroinflammation. Radioligands with PET accurately quantify TSPO in neuroinflammatory conditions. However, the existence of three human TSPO genotypes that show differential affinity to almost all useful TSPO PET radioligands hampers such studies. There is an unmet need for genotype-insensitive, high-affinity, and moderately lipophilic TSPO ligands that may serve as leads for PET radioligand development. To address this need, we varied the known high-affinity TSPO ligand (l)-N,N-diethyl-2-methyl-3-(2-phenylquinolin-4-yl)propanamide in its aryl scaffold, side chain tether, and pendant substituted amido group while retaining an N-methyl group as a site for labeling with carbon-11. From this effort, oxygen-tethered N-methyl-aryloxypropanamides emerged as new high-affinity TSPO ligands with attenuated lipophilicity, including one example with attractive properties for PET radioligand development, namely N-methyl-N-phenyl-2-[2-(pyridin-2-yl)quinolin-4-yl]oxy}propanamide (22a; rat K-i = 0.10 nM; human TSPO genotypes K-i = 1.4 nM; clogD = 4.18).
• New Access to Oxazolopyridines via Hydroxyamidine Derivatives; Application to Quinolines
  作者：Paul Caubère、Gérald Guillaumet、Ethel Garnier、Stéphanie Blanchard、Ivan Rodriguez、Christian Jarry、Jean-Michel Léger

  DOI：10.1055/s-2003-41052

  日期：——

  Several 2-aryl and 2-heteroaryloxazolo[4,5-b]pyridines were synthesised in high yields from zwitterion or hydroxyamidine derivatives by heating in dimethylacetamide. These intermediates were generated via hetarynic reaction with the complex base NaNH2-t-BuONa (5:2). The same reactions were possible with quinoline derivatives.

  通过在二甲基乙酰胺中加热，从齐聚物或羟基脒衍生物中高产合成了几种 2-芳基和 2-杂芳基恶唑并[4,5-b]吡啶。这些中间体是通过与络合碱 NaNH2-t-BuONa （5:2）发生热反应生成的。喹啉衍生物也可以发生同样的反应。

表征谱图