1-(4-fluorophenyl)-4-iodo-1H-1,2,3-triazole | 1086032-22-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-fluorophenyl)-4-iodo-1H-1,2,3-triazole
• 英文别名: 1-(4-fluorophenyl)-4-iodotriazole
• CAS: 1086032-22-5
• 化学式: C₈H₅FIN₃
• 分子量: 289.051
• InChiKey: NTCDNBXSALTPSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 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：
  30.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-fluorophenyl)-4-iodo-1H-1,2,3-triazole 、 N-Boc-1,2,5,6-四氢吡啶-4-硼酸频哪醇酯 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以60.9 mg的产率得到tert-butyl 4-[1-(4-fuluorophenyl)-1H-1,2,3-triazol-4-yl]-3,6-dihydropyridine-1(2H)-carboxylate
  参考文献：
  名称：

  Discovery and biological profile of 4-(1-aryltriazol-4-yl)-tetrahydropyridines as an orally active new class of metabotropic glutamate receptor 1 antagonist

  摘要：

  We describe here the discovery and the structure-activity relationship (SAR) of a series of 4-(1-Aryl-triazol-4- yl)-tetrahydropyridines as novel mGluR1 antagonists. Our extensive chemical modi. cation of lead compound 2 successfully led to fluoropyridine analogs 7j and 1 with improved in vivo antagonistic activities. Among the evaluated compounds, chemically stable urea analog 1 showed oral antagonistic activity at dose ranges of 10-30 mg/kg in an animal model. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.060
• 作为产物：
  描述：

  1-(4-fluorophenyl)-4-(tributylstannyl)-1H-1,2,3-triazole 在 碘 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以461 mg的产率得到1-(4-fluorophenyl)-4-iodo-1H-1,2,3-triazole
  参考文献：
  名称：

  Discovery and biological profile of 4-(1-aryltriazol-4-yl)-tetrahydropyridines as an orally active new class of metabotropic glutamate receptor 1 antagonist

  摘要：

  We describe here the discovery and the structure-activity relationship (SAR) of a series of 4-(1-Aryl-triazol-4- yl)-tetrahydropyridines as novel mGluR1 antagonists. Our extensive chemical modi. cation of lead compound 2 successfully led to fluoropyridine analogs 7j and 1 with improved in vivo antagonistic activities. Among the evaluated compounds, chemically stable urea analog 1 showed oral antagonistic activity at dose ranges of 10-30 mg/kg in an animal model. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.060

文献信息

• Methyl-2,2-difluoro-2-(fluorosulfonyl) acetate (MDFA)/copper (I) iodide mediated and tetrabutylammonium iodide promoted trifluoromethylation of 1-aryl-4-iodo-1,2,3-triazoles
  作者：Chiradeep Panja、Jayashankara Vaderapura Puttaramu、Thirumurugan Kothandarama Chandran、Roshan Y. Nimje、Hemantha Kumar、Anuradha Gupta、Pirama Nayagam Arunachalam、James R. Corte、Arvind Mathur

  DOI：10.1016/j.jfluchem.2020.109516

  日期：2020.8

  4-trifluoromethylated 1,2,3-triazoles. We report herein a general methodology for the trifluoromethylation of 1-aryl-4-iodo-1, 2, 3-triazoles. Tetrabutylammonium iodide (TBAI) has been shown to provide enhanced conversion in these CuI-mediated reaction using methyl 2,2-difluoro-2-(fluorosulfonyl)acetate (MDFA). The method exhibited broad functional group tolerance and was applied to the synthesis of a library of

  尽管有几种方法可用于合成大量的三氟甲基化杂环，但很少有方法可用于合成4-三氟甲基化的1,2,3-三唑。我们在此报告了1-芳基-4-碘-1、2、3-三唑的三氟甲基化的一般方法。在使用2，2-二氟-2-（氟磺酰基）乙酸甲酯（MDFA）的CuI介导的反应中，碘化四丁基铵（TBAI）已显示出增强的转化率。该方法表现出宽泛的官能团耐受性，并被用于以克为单位合成1-芳基-4-三氟甲基-1,2,3-三唑的文库。