2-Chloro-4-(furan-2-yl)-3-nitropyridine | 1265175-45-8

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2-Chloro-4-(furan-2-yl)-3-nitropyridine
• CAS: 1265175-45-8
• 化学式: C₉H₅ClN₂O₃
• 分子量: 224.603
• InChiKey: FONSDNIYTLGCPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Chloro-4-(furan-2-yl)-3-nitropyridine 在 sodium dithionite 、 水 、 乙酸酐 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 正丁醇 为溶剂， 反应 31.5h， 生成 7-(furan-2-yl)-3-(4-methoxybenzyl)-3H-imidazo[4,5-b]pyridine
  参考文献：
  名称：

  Synthesis and antimycobacterial activities of non-purine analogs of 6-aryl-9-benzylpurines: Imidazopyridines, pyrrolopyridines, benzimidazoles, and indoles

  摘要：

  6,9-Disubstituted purines and 7-deazapurines are known to be powerful inhibitors of Mycobacterium tuberculosis (Mtb) in vitro. Analogs modified in the six-membered ring (imidazopyridines, pyrrolopyridines, benzimidazoles, and indoles) were synthesized and evaluated as Mtb inhibitors. The targets were prepared by functionalization on the bicyclic heterocycle or from simple pyridines. The results reported herein, indicate that the purine N-1, but not N-3, is important for binding to the unknown target. The 3-deazapurines appears to be slightly more active compared to the parent purines and slightly less active than their 7-deazapurine isomers. Removal of both the purine N-3 and N-7 did not result in further enhanced antimycobacterial activity but the toxicity towards mammalian cells was increased. Both 3-deaza and 3,7-dideazapurines exhibited a modest activity against of the Mtb isolate in the state of non-replicating persistence. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.023
• 作为产物：
  描述：

  2,4-二氯-3-硝基吡啶 、 2-(三丁基锡烷基)呋喃 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以76%的产率得到2-Chloro-4-(furan-2-yl)-3-nitropyridine
  参考文献：
  名称：

  Reactivity and regioselectivity in Stille couplings of 3-substituted 2,4-dichloropyridines

  摘要：

  The influence of substituents at C-3 of 2,4-dichloropyridines on their reactivity and regioselectivity in Pd-catalyzed cross-couplings is studied. As a model reaction, the (Ph3P)(2)PdCl2-catalyzed Stille coupling between 2-furyl(tributyl)tin and pyridines is chosen. Increased electron-withdrawing ability of a substituent at the pyridine 3-position improves the overall reactivity. Absolute selectivity for coupling at C-2 is achieved with an amino group at C-3, and the selectivity is totally reversed when the amino group is exchanged for a nitro substituent. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.108