methyl 3-azido-1-({2-[(phenylcarbonyl)oxy]ethoxy}methyl)-1H-1,2,4-triazole-5-carboxylate | 1028825-49-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3-azido-1-({2-[(phenylcarbonyl)oxy]ethoxy}methyl)-1H-1,2,4-triazole-5-carboxylate
• 英文别名: Methyl 5-azido-2-(2-benzoyloxyethoxymethyl)-1,2,4-triazole-3-carboxylate；methyl 5-azido-2-(2-benzoyloxyethoxymethyl)-1,2,4-triazole-3-carboxylate
• CAS: 1028825-49-1
• 化学式: C₁₄H₁₄N₆O₅
• 分子量: 346.302
• InChiKey: XTRNBBWPPSYRMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 3-azido-1-({2-[(phenylcarbonyl)oxy]ethoxy}methyl)-1H-1,2,4-triazole-5-carboxylate 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 以93%的产率得到methyl 3-amino-1-({2-[(phenylcarbonyl)oxy]ethoxy}methyl)-1H-1,2,4-triazole-5-carboxylate
  参考文献：
  名称：

  铜介导的氨基三唑无环核苷的选择性N-芳基化

  摘要：

  新颖Ñ -aryltriazole核苷合成通过在Cu-体介导C  Ñ交叉偶联反应，使用3-氨基三唑acyclonucleosides和各种硼酸试剂。有趣的是，Ñ -arylation进行迅速得多上比在胺基团的酰胺基团，导致选择性Ñ的酰胺官能团-arylation上含有关于三唑核碱基两组核苷。

  DOI：

  10.1002/hlca.200900033
• 作为产物：
  描述：

  1-苯甲酰氧基-2-(氯甲氧基)乙烷 、 3-叠氮基-5-甲氧羰基-1,2,4-三唑 在 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以41.8%的产率得到methyl 3-azido-1-({2-[(phenylcarbonyl)oxy]ethoxy}methyl)-1H-1,2,4-triazole-5-carboxylate
  参考文献：
  名称：

  Bitriazolyl acyclonucleosides with antiviral activity against tobacco mosaic virus

  摘要：

  Bitriazolyl acyclonucleosides were synthesized via the Huisgen reaction and then subjected to ammonolysis. The antiviral activity of these nucleosides against tobacco mosaic virus (TMV) was assessed. Like the previously described bitriazolyl compounds, these new bitriazolyl acyclonucleosides were found to show anti-TMV activity. This suggests that the bitriazolyl moieties are important structural features involved in the antiviral activity of these compounds. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.02.139

文献信息

• Bitriazolyl acyclonucleosides with antiviral activity against tobacco mosaic virus
  作者：Wei Li、Yi Xia、Zhijin Fan、Fanqi Qu、Qiongyou Wu、Ling Peng

  DOI：10.1016/j.tetlet.2008.02.139

  日期：2008.4

  Bitriazolyl acyclonucleosides were synthesized via the Huisgen reaction and then subjected to ammonolysis. The antiviral activity of these nucleosides against tobacco mosaic virus (TMV) was assessed. Like the previously described bitriazolyl compounds, these new bitriazolyl acyclonucleosides were found to show anti-TMV activity. This suggests that the bitriazolyl moieties are important structural features involved in the antiviral activity of these compounds. (C) 2008 Elsevier Ltd. All rights reserved.
• Cu-Mediated Selective<i>N</i>-Arylation of Aminotriazole Acyclonucleosides
  作者：Wei Li、Yuting Fan、Yi Xia、Palma Rocchi、Ruizhi Zhu、Fanqi Qu、Johan Neyts、Juan L. Iovanna、Ling Peng

  DOI：10.1002/hlca.200900033

  日期：2009.8

  Novel N‐aryltriazole nucleosides were synthesized via a Cu‐mediated CN cross‐coupling reaction, using 3‐aminotriazole acyclonucleosides and various boronic acid reagents. Interestingly, N‐arylation proceeded much more rapidly on the amide group than on the amine group, leading to selective N‐arylation of the amide functionality on nucleosides containing both groups on the triazole nucleobase.

  新颖Ñ -aryltriazole核苷合成通过在Cu-体介导C  Ñ交叉偶联反应，使用3-氨基三唑acyclonucleosides和各种硼酸试剂。有趣的是，Ñ -arylation进行迅速得多上比在胺基团的酰胺基团，导致选择性Ñ的酰胺官能团-arylation上含有关于三唑核碱基两组核苷。