methyl 1-(4-fluorophenyl)-5-phenyl-1H-1,2,4-triazole-3-carboxylate | 1315307-45-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 1-(4-fluorophenyl)-5-phenyl-1H-1,2,4-triazole-3-carboxylate
• 英文别名: Methyl 1-(4-fluorophenyl)-5-phenyl-1,2,4-triazole-3-carboxylate
• CAS: 1315307-45-9
• 化学式: C₁₆H₁₂FN₃O₂
• 分子量: 297.289
• InChiKey: LMRQIPGORJKLMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯甲醛 在 盐酸羟胺 、 三乙胺 作用下， 以 甲苯 为溶剂， 生成 methyl 1-(4-fluorophenyl)-5-phenyl-1H-1,2,4-triazole-3-carboxylate
  参考文献：
  名称：

  An Effective Nitrilimine Cycloaddition for the Synthesis of 1,3,5-Trisubstituted 1,2,4-Triazoles from Oximes with Hydrazonoyl Hydrochlorides

  摘要：

  An effective 1,3-dipolar cycloaddition for the synthesis of 1,3,5-trisubstituted 1,2,4-triazole derivatives was developed by reacting oximes with hydrazonoyl hydrochlorides using triethylamine as a base. The desired 1,3,5-trisubstituted 1,2,4-triazoles were obtained in good yields and the reaction was applicable to aliphatic, cyclic aliphatic, aromatic and heterocyclic oxime substrates.

  DOI：

  10.1055/s-0030-1260759

文献信息

• 10.1021/acs.orglett.4c02130
  作者：Liang, Baihui、Wen, Tingting、Cai, Xiangya、Hu, Yutong、Nie, Biao、Ren, Weijie、Chen, Jiehao、Benedict Lo, Tsz Woon、Chen, Xiuwen、Zhu, Zhongzhi

  DOI：10.1021/acs.orglett.4c02130

  日期：——

  A novel [1+1+3] annulation of AgNOx, isocyanides, and isocyanates for the selective synthesis of 1,2,4-triazoles is presented herein. In this transformation, AgNOx and isocyanates are used as nitrogen sources instead of the traditional hydrazine or diazonium reagents. This process also involves N–O/C–H/C═N bond cleavage and the construction of new N–N/C–N bonds with a good substrate scope and functional

  本文提出了一种用于选择性合成 1,2,4-三唑的 AgNOx、异氰化物和异氰酸酯的新型 [1+1+3] 环化。在此转化中，AgNOx 和异氰酸酯用作氮源，而不是传统的肼或重氮试剂。该过程还涉及 N-O/C-H/C=N 键断裂以及具有良好底物范围和官能团耐受性的新 N-N/C-N 键的构建。
• Cycloaddition reactions of glycine imine anions to phenylazocarboxylic esters – a new access to 1,3,5-trisubstituted 1,2,4-triazoles
  作者：Roman Lasch、Markus R. Heinrich

  DOI：10.1016/j.tet.2015.04.078

  日期：2015.6

  Phenylazocarboxylic tert-butyl esters have recently been shown to be highly versatile building blocks due to their ability to undergo nucleophilic aromatic substitutions under mild conditions, particularly well with [F-18]fluoride, and to act as precursors for aryl radicals. In this article, we now report first examples for cycloaddition reactions to phenylazocarboxylates. In a one-pot reaction with readily accessible glycine imines, a variety of highly substituted 1,2,4-triazoles could be obtained. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis and antiproliferative evaluation of 3,5-disubstituted 1,2,4-triazoles containing flurophenyl and trifluoromethanephenyl moieties
  作者：Li-Ya Wang、Wen-Che Tseng、Tian-Shung Wu、Kimiyoshi Kaneko、Hiroyuki Takayama、Masayuki Kimura、Wen-Chin Yang、Jin Bin Wu、Shin-Hun Juang、Fung Fuh Wong

  DOI：10.1016/j.bmcl.2011.07.009

  日期：2011.9

  An efficient 1,3-dipolar cycloaddition method was performed for the synthesis of a series of monofluoroand trifluoromethane-3,5-disubstituted 1,2,4-triazoles. This efficient cycloaddition method was to react hydrazonoyl hydrochlorides with a series of aldehydes in the presence of NEt(3) as catalytic basic agent to provide the corresponding product in 28-94%. Their growth inhibitory results against cancer cells indicated that some of the fluorine-and trifluoromethane-containing compounds could effectively inhibit the growth of NCI-H226 and T-cell leukemia (Jurkat) cells. Among the compounds, trifluoromethane-containing 1,2, 4-triazoles possessed the five-membered ring groups on the C-5 position of the triazolic ring, including cyclopentyl, 3-furyl, 3-thienyl, and 2-pyrrolyl, possessed the significant inhibitory activity for NCI-H226 cancer cells. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.
• ‘One-flask’ synthesis to 3,5-disubstituted 1,2,4-triazoles from aldehydes with hydrazonoyl hydrochlorides via 1,3-dipolar cycloaddition
  作者：Wen-Che Tseng、Li-Ya Wang、Tian-Shung Wu、Fung Fuh Wong

  DOI：10.1016/j.tet.2011.05.003

  日期：2011.7

  A new 'one-flask' synthesis of 3,5-disubstituted 1,2,4-triazoles has successfully been developed to synthesize a series of 3,5-disubstituted 1,2,4-triazoles. The transformation involves the 1,3-dipolar cycloaddition reaction of hydrazonoyl hydrochlorides with oxime intermediates prepared from aldehydes with hydroxylamine hydrochloride in the presence of excess amount of triethylamine. In this 'one-flask' 1,3-dipolar reaction, hydrazonoyl hydrochlorides was concerned as the masked 1,3-dipole nitrilimine under basic condition. Furthermore, this newly developed methodology can be applied to various aldehyde substrates including aliphatic, cyclic aliphatic, aromatic, and heterocyclic aldehydes. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.
• An Effective Nitrilimine Cycloaddition for the Synthesis of 1,3,5-Trisubstituted 1,2,4-Triazoles from Oximes with Hydrazonoyl Hydrochlorides
  作者：Fung Wong、Li-Ya Wang、Wen-Che Tseng、Hui-Yi Lin

  DOI：10.1055/s-0030-1260759

  日期：2011.6

  An effective 1,3-dipolar cycloaddition for the synthesis of 1,3,5-trisubstituted 1,2,4-triazole derivatives was developed by reacting oximes with hydrazonoyl hydrochlorides using triethylamine as a base. The desired 1,3,5-trisubstituted 1,2,4-triazoles were obtained in good yields and the reaction was applicable to aliphatic, cyclic aliphatic, aromatic and heterocyclic oxime substrates.