1-(2-trifluoromethylphenyl)-3-methoxycarbonyl-5-methyl-1,2,4-triazole | 1315307-31-3

• 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-(2-trifluoromethylphenyl)-3-methoxycarbonyl-5-methyl-1,2,4-triazole
• 英文别名: 1-(2-trifluorophenyl)-3-methoxycarbonyl-5-methyl-1,2,4-triazole；Methyl 5-methyl-1-[2-(trifluoromethyl)phenyl]-1,2,4-triazole-3-carboxylate
• CAS: 1315307-31-3
• 化学式: C₁₂H₁₀F₃N₃O₂
• 分子量: 285.226
• InChiKey: WMRUGVCKUJQSKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  邻氨基三氟甲苯 在 盐酸 、 三乙胺 、 sodium nitrite 作用下， 以 甲苯 为溶剂， 生成 1-(2-trifluoromethylphenyl)-3-methoxycarbonyl-5-methyl-1,2,4-triazole
  参考文献：
  名称：

  ‘One-flask’ synthesis to 3,5-disubstituted 1,2,4-triazoles from aldehydes with hydrazonoyl hydrochlorides via 1,3-dipolar cycloaddition

  摘要：

  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.

  DOI：

  10.1016/j.tet.2011.05.003

文献信息

• One-flask synthesis of 1,3,5-trisubstituted 1,2,4-triazoles from nitriles and hydrazonoyl chlorides via 1,3-dipolar cycloaddition
  作者：Li-Ya Wang、Henry J. Tsai、Hui-Yi Lin、Kimiyoshi Kaneko、Fen-Ying Cheng、Hsin-Siao Shih、Fung Fuh Wong、Jiann-Jyh Huang

  DOI：10.1039/c4ra00113c

  日期：——

  One-flask synthesis of 1,3,5-trisubstituted 1,2,4-triazoles from nitriles and hydrazonoyl chlorides via 1,3-dipolar cycloaddition.

  一瓶法合成1,3,5-三取代-1,2,4-三唑，从腈和叠氮酰氯通过1,3-偶极环加成。
• 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.
• 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.