N-(2,3-Dimethyl-1-benzothiophen-7-yl)pyridin-3-amine | 924660-98-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: N-(2,3-Dimethyl-1-benzothiophen-7-yl)pyridin-3-amine
• CAS: 924660-98-0
• 化学式: C₁₅H₁₄N₂S
• 分子量: 254.356
• InChiKey: SEBQFGNOHXROGE-UHFFFAOYSA-N

物化性质

• 熔点：
  161-163 °C(Solv: ethyl ether (60-29-7); ligroine (8032-32-4))
• 沸点：
  458.5±40.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-氨基吡啶 、 2,3-二甲基-1-苯并噻吩-7-胺 在 palladium diacetate caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 以76%的产率得到N-(2,3-Dimethyl-1-benzothiophen-7-yl)pyridin-3-amine
  参考文献：
  名称：

  Synthesis and antioxidant activity evaluation of new 7-aryl or 7-heteroarylamino-2,3-dimethylbenzo[b]thiophenes obtained by Buchwald–Hartwig C–N cross-coupling

  摘要：

  New 7-aryl or 7-heteroarylamino-2,3-dimethylbenzo[b]thiophenes were prepared by palladium-catalyzed Buchwald-Hartwig cross-coupling of 7-bromo or 7-amino-2,3-dimethylbenzo[b]thiophenes, previously prepared by us, with substituted (4-methoxy or 3,4-dimethoxy) anilines and 3-aminopyridine or with substituted (3-methoxy or 4-cyano) bromobenzenes and 2-bromopyridine, respectively, using Pd(OAc)(2), rac-BINAP or Xamphos as ligands, and Cs2CO3 as base. Their antioxidant properties were evaluated by several methods: reducing power, scavenging effect on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals, inhibition of erythrocyte hemolysis and inhibition of lipid peroxidation using the beta-carotene linoleate system. EC50 values for all the methods were determined and it was possible to establish some structure-activity relationships (SARs) based on the presence and position of different substituents on the phenyl ring (1 or 2 OMe and C equivalent to N), on the presence of a pyridine ring and on the position of its nitrogen atom relative to the N-H bond. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.11.035

文献信息

• Synthesis and antioxidant activity evaluation of new 7-aryl or 7-heteroarylamino-2,3-dimethylbenzo[b]thiophenes obtained by Buchwald–Hartwig C–N cross-coupling
  作者：Maria-João R.P. Queiroz、Isabel C.F.R. Ferreira、Ricardo C. Calhelha、Letícia M. Estevinho

  DOI：10.1016/j.bmc.2006.11.035

  日期：2007.2

  New 7-aryl or 7-heteroarylamino-2,3-dimethylbenzo[b]thiophenes were prepared by palladium-catalyzed Buchwald-Hartwig cross-coupling of 7-bromo or 7-amino-2,3-dimethylbenzo[b]thiophenes, previously prepared by us, with substituted (4-methoxy or 3,4-dimethoxy) anilines and 3-aminopyridine or with substituted (3-methoxy or 4-cyano) bromobenzenes and 2-bromopyridine, respectively, using Pd(OAc)(2), rac-BINAP or Xamphos as ligands, and Cs2CO3 as base. Their antioxidant properties were evaluated by several methods: reducing power, scavenging effect on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals, inhibition of erythrocyte hemolysis and inhibition of lipid peroxidation using the beta-carotene linoleate system. EC50 values for all the methods were determined and it was possible to establish some structure-activity relationships (SARs) based on the presence and position of different substituents on the phenyl ring (1 or 2 OMe and C equivalent to N), on the presence of a pyridine ring and on the position of its nitrogen atom relative to the N-H bond. (c) 2006 Elsevier Ltd. All rights reserved.