1-(3-Methoxybenzyl)-4,5-dibromo-1H-1,2,3-triazole | 1248676-64-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(3-Methoxybenzyl)-4,5-dibromo-1H-1,2,3-triazole
• 英文别名: 4,5-dibromo-1-[(3-methoxyphenyl)methyl]triazole
• CAS: 1248676-64-3
• 化学式: C₁₀H₉Br₂N₃O
• 分子量: 347.009
• InChiKey: BGADGJBLDXCEDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4,5-二溴-2H-1,2,3-三唑 、 3-甲氧基溴苄 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4,5-Dibromo-2-(3-methoxybenzyl)-2H-1,2,3-triazole 、 1-(3-Methoxybenzyl)-4,5-dibromo-1H-1,2,3-triazole
  参考文献：
  名称：

  General Solution to the Synthesis of N-2-Substituted 1,2,3-Triazoles

  摘要：

  The regioselective N-alkylation of 1,2,3-triazoles 1-6 was studied Good to excellent N-2 selectivity and high chemical yields for N-2-substituted 4,5-dibromotriazoles 7 were obtained with 4,5-dibromo- and 4-bromo-5-trimethylsilyl-1,2,3-triazoles These building blocks can be readily converted to 2-mono-, 2,4-di-, and 2,4,5-polysubstituted triazoles 10-15, providing a general, protective, group-free method for the synthesis of N-2-substituted triazoles. Observed regioselectivities can be rationalized by a combination of Frontier Molecular Orbital, steric, and electrostatic directing effects on the heterocyclic scaffolds

  DOI：

  10.1021/ol101965a

文献信息

• Preparation method for 1-substituted-1H-1,2,3-triazole 4-carboxylic acid
  申请人：ABA CHEMICALS (SHANGHAI) LIMITED

  公开号：US10487063B2

  公开（公告）日：2019-11-26

  Provided is a preparation method for 1-substituted-1H-1, 2, 3-triazole-4-carboxylic acid. 1-Substituted-4, 5-dibromo-1H-1,2,3-triazole is added to an isopropylmagnesium chloride to obtain 1-substituted-4-bromo-1H-1,2,3-triazole by a reaction; then an isopropylmagnesium chloride-lithium chloride composite is added directly to obtain a mixture of 1-substituted-1H-1,2,3-triazole-4-carboxylic acid and 1-substituted-4-bromo-1H-1,2,3-triazole-5-carboxylic acid; secondly, to the mixture, a base and iodomethane are added to obtain 1-substituted-4-bromo-1H-1,2,3-triazole-5-carboxylic acid methyl ester by a reaction; the aqueous layer is adjusted with hydrochloric acid to pH=1-5, extracted with an organic solvent and dried; then 1-substituted-1H-1,2,3-triazole-4-carboxylic acid is obtained by concentration and crystallization. The method is suitable for industrialized production and has a greater application value.

  本发明提供了一种 1-取代-1H-1,2,3-三唑-4-羧酸的制备方法。将 1-取代-4，5-二溴-1H-1,2,3-三唑加入到异丙基氯化镁中，通过反应得到 1-取代-4-溴-1H-1,2,3-三唑；然后直接加入异丙基氯化镁-氯化锂复合物，得到 1-取代-1H-1,2,3-三唑-4-羧酸和 1-取代-4-溴-1H-1,2,3-三唑-5-羧酸的混合物；其次，在混合物中加入碱和碘甲烷，通过反应得到 1-取代-4-溴-1H-1,2,3-三唑-5-羧酸甲酯；水层用盐酸调节 pH=1-5 后，用有机溶剂萃取并干燥；然后通过浓缩和结晶得到 1-取代-1H-1,2,3-三唑-4-羧酸。该方法适合工业化生产，具有较大的应用价值。
• [EN] PREPARATION METHOD FOR 1-SUBSTITUTED-4-BROMINE-1H-1,2,3-TRIAZOLE-5-CARBOXYLIC ACID<br/>[FR] PROCÉDÉ DE PRÉPARATION D'UN ACIDE CARBOXYLIQUE 1-SUBSTITUÉ-4-BROMURE-1H-1,2,3-TRIAZOLE-5
  申请人：ABA CHEMICALS CORP

  公开号：WO2013127028A1

  公开（公告）日：2013-09-06

  一种1-取代-4-溴-1H-1，2，3-三氮唑-5-羧酸的制备方法，该方法以4，5-二溴-2H-1，2，3-三氮唑为原料，经过若干次反应后得到1-取代-4-溴-1H-1，2，3-三氮唑-5-羧酸。
• Preparation Method for 1-substituted-1H-1,2,3-triazole 4-carboxylic acid
  申请人：ABA CHEMICALS (SHANGHAI) LIMITED

  公开号：US20180029999A1

  公开（公告）日：2018-02-01

  Provided is a preparation method for 1-substituted-1H-1, 2, 3-triazole-4-carboxylic acid. 1-Substituted-4, 5-dibromo-1H-1,2,3-triazole is added to an isopropylmagnesium chloride to obtain 1-substituted-4-bromo-1H-1,2,3-triazole by a reaction; then an isopropylmagnesium chloride-lithium chloride composite is added directly to obtain a mixture of 1-substituted-1H-1,2,3-triazole-4-carboxylic acid and 1-substituted-4-bromo-1H-1,2,3-triazole-5-carboxylic acid; secondly, to the mixture, a base and iodomethane are added to obtain 1-substituted-4-bromo-1H-1,2,3-triazole-5-carboxylic acid methyl ester by a reaction; the aqueous layer is adjusted with hydrochloric acid to pH=1-5, extracted with an organic solvent and dried; then 1-substituted-1H-1,2,3-triazole-4-carboxylic acid is obtained by concentration and crystallization. The method is suitable for industrialized production and has a greater application value.
• General Solution to the Synthesis of <i>N</i>-2-Substituted 1,2,3-Triazoles
  作者：Xiao-jun Wang、Li Zhang、Dhileepkumar Krishnamurthy、Chris H. Senanayake、Peter Wipf

  DOI：10.1021/ol101965a

  日期：2010.10.15

  The regioselective N-alkylation of 1,2,3-triazoles 1-6 was studied Good to excellent N-2 selectivity and high chemical yields for N-2-substituted 4,5-dibromotriazoles 7 were obtained with 4,5-dibromo- and 4-bromo-5-trimethylsilyl-1,2,3-triazoles These building blocks can be readily converted to 2-mono-, 2,4-di-, and 2,4,5-polysubstituted triazoles 10-15, providing a general, protective, group-free method for the synthesis of N-2-substituted triazoles. Observed regioselectivities can be rationalized by a combination of Frontier Molecular Orbital, steric, and electrostatic directing effects on the heterocyclic scaffolds