Methyl 2-(2-acetyloxyethoxymethyl)-5-anilino-1,2,4-triazole-3-carboxylate | 1258402-86-6

• 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 2-(2-acetyloxyethoxymethyl)-5-anilino-1,2,4-triazole-3-carboxylate
• 英文别名: methyl 2-(2-acetyloxyethoxymethyl)-5-anilino-1,2,4-triazole-3-carboxylate
• CAS: 1258402-86-6
• 化学式: C₁₅H₁₈N₄O₅
• 分子量: 334.332
• InChiKey: UCUJXGXBXQYRRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Methyl 2-(2-acetyloxyethoxymethyl)-5-anilino-1,2,4-triazole-3-carboxylate 在 氨 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以90%的产率得到1-((2-hydroxyethoxy)methyl)-3-(phenylamino)-1H-1,2,4-triazole-5-carboxamide
  参考文献：
  名称：

  Ligand-Mediated Highly Effective and Selective C−N Coupling for Synthesizing BioactiveN-Aryltriazole Acyclonucleosides

  摘要：

  N-aryltriazole nucleosides are new chemical entities with potential biological activity. The two phosphor ligands, Synphos and Xantphos, had a selective and effective impact on Pd-catalyzed C-N coupling with the 5- and 3-bromotriazole acyclonucleoside isomers, affording the corresponding and otherwise difficult to achieve N-aryltriazole nucleosides with good to excellent yields. In addition, two of the synthesized nucleosides showed superior anticancer activity against drug-resistant pancreatic cancer, compared to the reference drug gemcitabine.

  DOI：

  10.1021/ol102537p
• 作为产物：
  描述：

  methyl 3-bromo-1-[(2-acetoxyethoxy)methyl]-1,2,4-triazole-5-carboxylate 、 苯胺 在 (S)-(-)-[(5,6),(5',6')-双(乙烯二氧)联苯-2,2'-基]二苯基磷 、 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以89%的产率得到Methyl 2-(2-acetyloxyethoxymethyl)-5-anilino-1,2,4-triazole-3-carboxylate
  参考文献：
  名称：

  一种高效的混合配体钯催化体系，促进ç ？N偶联用于合成N-芳基氨基三唑核苷

  摘要：

  使其独一无二！的Pd / Synphos /加入Xantphos的混合配体系统促进有效的C  N的各个的合成耦合Ñ -arylaminotriazole和Ñ -arylaminopurine核苷类似物。该催化体系是惊人地有力和有效的，从而允许无与伦比的底物范围和高的产物收率以及促进的C 对于C Cl键活化 N个耦合（参见方案）。

  DOI：

  10.1002/chem.201103918

文献信息

• An Efficient Mixed-Ligand Pd Catalytic System to Promote CN Coupling for the Synthesis of N-Arylaminotriazole Nucleosides
  作者：Yuting Fan、Yi Xia、Jingjie Tang、Fabio Ziarelli、Fanqi Qu、Palma Rocchi、Juan L. Iovanna、Ling Peng

  DOI：10.1002/chem.201103918

  日期：2012.2.20

  Make it unique! A mixed‐ligand system of Pd/Synphos/Xantphos promotes effective CN coupling in the synthesis of various N‐arylaminotriazole and N‐arylaminopurine nucleoside analogues. This catalytic system is strikingly powerful and efficient, allowing for unparalleled substrate scope and high product yields as well as promotion of CCl bond activation for CN coupling (see scheme).

  使其独一无二！的Pd / Synphos /加入Xantphos的混合配体系统促进有效的C  N的各个的合成耦合Ñ -arylaminotriazole和Ñ -arylaminopurine核苷类似物。该催化体系是惊人地有力和有效的，从而允许无与伦比的底物范围和高的产物收率以及促进的C 对于C Cl键活化 N个耦合（参见方案）。
• Ligand-Mediated Highly Effective and Selective C−N Coupling for Synthesizing Bioactive<i>N</i>-Aryltriazole Acyclonucleosides
  作者：Yuting Fan、Yi Xia、Jingjie Tang、Palma Rocchi、Fanqi Qu、Juan Iovanna、Ling Peng

  DOI：10.1021/ol102537p

  日期：2010.12.17

  N-aryltriazole nucleosides are new chemical entities with potential biological activity. The two phosphor ligands, Synphos and Xantphos, had a selective and effective impact on Pd-catalyzed C-N coupling with the 5- and 3-bromotriazole acyclonucleoside isomers, affording the corresponding and otherwise difficult to achieve N-aryltriazole nucleosides with good to excellent yields. In addition, two of the synthesized nucleosides showed superior anticancer activity against drug-resistant pancreatic cancer, compared to the reference drug gemcitabine.
• Pd(dba)₂ vs Pd₂(dba)₃: An in-Depth Comparison of Catalytic Reactivity and Mechanism via Mixed-Ligand Promoted C–N and C–S Coupling Reactions
  作者：Mei Cong、Yuting Fan、Jean-Manuel Raimundo、Jingjie Tang、Ling Peng

  DOI：10.1021/ol501600k

  日期：2014.8.15

  With the help of mixed ligand catalytic systems, the analogous mechanisms behind the cognate performance by Pd(dba)2 and Pd2(dba)3 in catalyzing C-N and C-S coupling reactions were demonstrated. This information is instrumental in organic synthesis requiring Pd-catalyzed cross-coupling reactions and may also be valuable to other Pd-catalyzed transformations.