ethyl 4-(2'-methoxyphenyl)-1H-1,2,3-trizole-5-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 4-(2'-methoxyphenyl)-1H-1,2,3-trizole-5-carboxylate
• 英文别名: ethyl 4-(2-methoxyphenyl)-1H-1,2,3-triazole-5-carboxylate；ethyl 5-(2-methoxyphenyl)-2H-triazole-4-carboxylate
• 化学式: C₁₂H₁₃N₃O₃
• 分子量: 247.254
• InChiKey: FHIICCXABIOVQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (E)-1-carboethoxy-2-(2'-methoxyphenyl)-1-nitroethene 在 叠氮基三甲基硅烷 、 四丁基氟化铵 作用下， 反应 8.0h， 以75%的产率得到ethyl 4-(2'-methoxyphenyl)-1H-1,2,3-trizole-5-carboxylate
  参考文献：
  名称：

  Synthesis of 4-Aryl-1H-1,2,3-triazoles through TBAF-Catalyzed [3 + 2] Cycloaddition of 2-Aryl-1-nitroethenes with TMSN₃ under Solvent-Free Conditions

  摘要：

  TBAF-catalyzed [3 + 2] cycloaddition reactions of 2-aryl-1-cyano- or 2-aryl-1-carbethoxy-1-nitroethenes 1 with TMSN3 under SFC allow the corresponding 4-aryl-5-eyano- or 4-aryl-5-carbethoxy-1H-1,2,3-triazoles 2 to be prepared under mild reaction conditions and with good to excellent yields (70-90%). The proposed protocol does not require dried glassware or inert atmosphere.

  DOI：

  10.1021/jo0507845

文献信息

• Metal-Free Multicomponent Reaction for Synthesis of 4,5-Disubstituted 1,2,3-(<i>NH</i> )-Triazoles
  作者：Guang-Long Wu、Qin-Pei Wu

  DOI：10.1002/adsc.201701587

  日期：2018.5.16

  A metal‐free domino reaction was developed for efficient synthesis of 4,5‐disubstituted 1,2,3‐(NH)‐triazoles by sequentially coupling sulfur salts with aldehydes and sodium azide. In the presence of L‐proline, olefinic sulfur salt intermediates rather than epoxides are formed in situ via the coupling of sulfur salts with aldehydes and cyclize with azide ion. This process features mild conditions, high

  通过顺序地将硫盐与醛和叠氮化钠偶联，开发了一种无金属的多米诺反应，可有效合成4,5-二取代的1,2,3-（NH）-三唑。在L-脯氨酸存在下，通过硫盐与醛的偶合并与叠氮化物离子环合，就可以在原位形成烯属硫盐中间体而不是环氧化物。该工艺具有温和的条件，高效率，可商购的起始原料以及广泛的底物范围。
• A Mild Multi-Component Reaction for the Synthesis of 4,5-Disubstituted 1H-1,2,3-Triazoles from Phosphonium Salts, Aldehydes, and Sodium Azide
  作者：Qin-Pei Wu、Guang-Long Wu

  DOI：10.1055/s-0037-1609720

  日期：2018.7

  series of representative 4,5-disubstituted 1H-1,2,3-triazoles were prepared. A mild and metal-free multi-component reaction to synthesize 4,5-disubstituted 1H-1,2,3-triazoles from phosphonium salts, aldehydes, and sodium azide is described. The process undergoes an organocatalyzed coupling of formyl group with phosphonium to form a key intermediate, olefinic phosphonium salt, which is followed by the [3+2]

  摘要 描述了一种温和且无金属的多组分反应，该反应可从phospho盐，醛和叠氮化钠合成4,5-二取代的1 H -1,2,3-三唑。该方法经历甲酰基与phospho的有机催化偶联以形成关键的中间体烯烃phospho盐，然后将叠氮化物的[3 + 2]环加成到活化的烯烃上。制备了一系列代表性的4，5-二取代的1 H -1,2,3-三唑。 描述了一种温和且无金属的多组分反应，该反应可从phospho盐，醛和叠氮化钠合成4,5-二取代的1 H -1,2,3-三唑。该方法经历甲酰基与phospho的有机催化偶联以形成关键的中间体烯烃phospho盐，然后将叠氮化物的[3 + 2]环加成到活化的烯烃上。制备了一系列代表性的4，5-二取代的1 H -1,2,3-三唑。
• Synthesis of 4-Aryl-1<i>H</i>-1,2,3-triazoles through TBAF-Catalyzed [3 + 2] Cycloaddition of 2-Aryl-1-nitroethenes with TMSN₃ under Solvent-Free Conditions
  作者：David Amantini、Francesco Fringuelli、Oriana Piermatti、Ferdinando Pizzo、Ennio Zunino、Luigi Vaccaro

  DOI：10.1021/jo0507845

  日期：2005.8.1

  TBAF-catalyzed [3 + 2] cycloaddition reactions of 2-aryl-1-cyano- or 2-aryl-1-carbethoxy-1-nitroethenes 1 with TMSN3 under SFC allow the corresponding 4-aryl-5-eyano- or 4-aryl-5-carbethoxy-1H-1,2,3-triazoles 2 to be prepared under mild reaction conditions and with good to excellent yields (70-90%). The proposed protocol does not require dried glassware or inert atmosphere.