1-[(2-(2-hydroxyethyl)-2H-1,2,3-triazol-4-yl)methyl]-5-methylpyrimidine-2,4(1H,3H)-dione | 1352744-37-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-[(2-(2-hydroxyethyl)-2H-1,2,3-triazol-4-yl)methyl]-5-methylpyrimidine-2,4(1H,3H)-dione
• 英文别名: 1-[[2-(2-Hydroxyethyl)triazol-4-yl]methyl]-5-methylpyrimidine-2,4-dione；1-[[2-(2-hydroxyethyl)triazol-4-yl]methyl]-5-methylpyrimidine-2,4-dione
• CAS: 1352744-37-6
• 化学式: C₁₀H₁₃N₅O₃
• 分子量: 251.245
• InChiKey: IZNWNKONTGSVCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-(pivaloyloxymethyl)-1-propargylthymine 在 ammonium hydroxide 、 叠氮基三甲基硅烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 49.0h， 生成 1-[(2-(2-hydroxyethyl)-2H-1,2,3-triazol-4-yl)methyl]-5-methylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis of 1,2,3-triazolo-nucleosides via the post-triazole N-alkylation

  摘要：

  2-Substituted-2H-1,2,3-triazolo-nucleosides with 3-phosphonopropyl, 2-hydroxyethyl, 2-cyanoethyl, carbamoylmethyl, or 1-deoxy-2,5-anhydro-D-mannitol-1-yl on the triazole N-2 nitrogen atom were obtained via the DBU-promoted N-alkylation of 3-(pivaloyloxymethyl)-1-[(NH-1,2,3-triazol-4-yl)methyl] thymine with diethyl 3-bromopropylphoshonate, 2-bromoethanol, acrylonitrile, methyl bromoacetate, or 3,4,6-tris(O-benzoyl)-2,5-anhydro-D-mannitol 1-tosylate. The N-2/N-1 regioselectivity of the alkylation varied from 57/43 (methyl bromoacetate) to 97/3 (diethyl 3-bromopropylphoshonate). The 1-substituted-1H-1,2,3-triazoles, when formed in the appreciated amount in the alkylation reaction, were converted into the corresponding 1-substituted-1H-1,2,3-triazolo-nucleosides. The substitution pattern of 2-substituted-2H-1,2,3-triazolo-nucleosides was confirmed by H-1-N-15 HMBC NMR spectra; the triazole nitrogen atoms were identified through their correlations with the triazole exo-cyclic protons. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.067

文献信息

• Synthesis of 1,2,3-triazolo-nucleosides via the post-triazole N-alkylation
  作者：Mariola Koszytkowska-Stawińska、Ewa Mironiuk-Puchalska、Tomasz Rowicki

  DOI：10.1016/j.tet.2011.10.067

  日期：2012.1

  2-Substituted-2H-1,2,3-triazolo-nucleosides with 3-phosphonopropyl, 2-hydroxyethyl, 2-cyanoethyl, carbamoylmethyl, or 1-deoxy-2,5-anhydro-D-mannitol-1-yl on the triazole N-2 nitrogen atom were obtained via the DBU-promoted N-alkylation of 3-(pivaloyloxymethyl)-1-[(NH-1,2,3-triazol-4-yl)methyl] thymine with diethyl 3-bromopropylphoshonate, 2-bromoethanol, acrylonitrile, methyl bromoacetate, or 3,4,6-tris(O-benzoyl)-2,5-anhydro-D-mannitol 1-tosylate. The N-2/N-1 regioselectivity of the alkylation varied from 57/43 (methyl bromoacetate) to 97/3 (diethyl 3-bromopropylphoshonate). The 1-substituted-1H-1,2,3-triazoles, when formed in the appreciated amount in the alkylation reaction, were converted into the corresponding 1-substituted-1H-1,2,3-triazolo-nucleosides. The substitution pattern of 2-substituted-2H-1,2,3-triazolo-nucleosides was confirmed by H-1-N-15 HMBC NMR spectra; the triazole nitrogen atoms were identified through their correlations with the triazole exo-cyclic protons. (C) 2011 Elsevier Ltd. All rights reserved.