5-methyl-1-[(2-(3-phosphonopropyl)-2H-1,2,3-triazol-4-yl)methyl]pyrimidine-2,4(1H,3H)-dione | 1352744-39-8

• 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: 5-methyl-1-[(2-(3-phosphonopropyl)-2H-1,2,3-triazol-4-yl)methyl]pyrimidine-2,4(1H,3H)-dione
• 英文别名: 3-[4-[(5-Methyl-2,4-dioxopyrimidin-1-yl)methyl]triazol-2-yl]propylphosphonic acid；3-[4-[(5-methyl-2,4-dioxopyrimidin-1-yl)methyl]triazol-2-yl]propylphosphonic acid
• CAS: 1352744-39-8
• 化学式: C₁₁H₁₆N₅O₅P
• 分子量: 329.252
• InChiKey: DDSIEILWRNAICZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  138
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-[(2-(3-(diethoxyphosphoryl)propyl)-2H-1,2,3-triazol-4-yl)methyl]-5-methyl-3-(pivaloyloxymethyl)pyrimidine-2,4(1H,3H)-dione 在 ammonium hydroxide 、 三甲基溴硅烷 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 1.0h， 生成 5-methyl-1-[(2-(3-phosphonopropyl)-2H-1,2,3-triazol-4-yl)methyl]pyrimidine-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.