4-(5-苯基-1H-1,2,3-三唑-1-基)苯甲酸乙酯 | 1003001-01-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-(5-苯基-1H-1,2,3-三唑-1-基)苯甲酸乙酯
• 英文名称: ethyl 4-(5-phenyl-1H-1,2,3-triazol-1-yl)benzoate
• 英文别名: Ethyl 4-(5-phenyltriazol-1-yl)benzoate；ethyl 4-(5-phenyltriazol-1-yl)benzoate
• CAS: 1003001-01-1
• 化学式: C₁₇H₁₅N₃O₂
• 分子量: 293.325
• InChiKey: YUJUGRJJFSOXGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(5-苯基-1H-1,2,3-三唑-1-基)苯甲酸乙酯 在 水 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 9H-fluoren-9-yl 3,3-dimethyl-7-oxo-6-(4-(5-phenyl-1H-1,2,3-triazol-1-yl)benzamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
  参考文献：
  名称：

  一种含三氮唑青霉素分子的合成方法及其应用

  摘要：

  本发明公开了一种含三氮唑青霉素分子的合成方法及其应用，对6－氨基青霉烷酸上羧基进行保护后合成化合物CX‑1或/和化合物CX‑2或/和化合物CX‑3，本发明制得的含有三氮唑的青霉素分子对β‑内酰胺酶具有明显的抑制作用。

  公开号：

  CN115894522A
• 作为产物：
  描述：

  ethyl 4-(5-phenyl-4-(phenylthio)-1H-1,2,3-triazol-1-yl)benzoate 在 Raney Nickel 作用下， 以 乙醇 为溶剂， 以85%的产率得到4-(5-苯基-1H-1,2,3-三唑-1-基)苯甲酸乙酯
  参考文献：
  名称：

  An Organocatalytic Regiospecific Synthesis of 1,5-Disubstituted 4-Thio-1,2,3-triazoles and 1,5-Disubstituted 1,2,3-Triazoles

  摘要：

  AbstractOrganocatalytic azide–ketone [3+2] cycloaddition (OrgAKC) of a variety of 1‐aryl‐2‐(arylthio)ethanones and 1‐alkyl‐2‐(alkylthio)ethanones with different aryl or alkyl azides is reported in dimethyl sulfoxide or solvent‐free under ambient conditions to furnish 1,5‐disubstituted 4‐thio‐1,2,3‐triazoles in a regiospecific manner, which are further converted into useful 1,5‐disubstituted 1,2,3‐triazoles by treatment with Raney Ni at 25 °C for 1–3 h. Notable features of the OrgAKC reaction include high rate and selectivity, solvent‐free conditions, easily available substrates and catalysts, a wide range of synthetic and medicinal applications, and excellent yields generating a vast library of triazoles.

  DOI：

  10.1002/chem.201503302

文献信息

• Ruthenium-Catalyzed Cycloaddition of Aryl Azides and Alkynes
  作者：Lars Kyhn Rasmussen、Brant C. Boren、Valery V. Fokin

  DOI：10.1021/ol701912s

  日期：2007.12.1

  The formation of 1,5-disubstituted 1,2,3-triazoles from aryl azides and alkynes was readily accomplished using [Cp*RuCl]4 catalyst in dimethylformamide. It was also demonstrated that the reaction provided higher yields, cleaner product, and shorter reaction times when carried out under microwave irradiation.

  使用在二甲基甲酰胺中的[Cp * RuCl] 4催化剂，很容易完成由芳基叠氮化物和炔烃形成的1,5-二取代的1,2,3-三唑。还证明了当在微波辐射下进行时，该反应提供更高的产率，更清洁的产物和更短的反应时间。
• Zinc Mediated Azide–Alkyne Ligation to 1,5- and 1,4,5-Substituted 1,2,3-Triazoles
  作者：Christopher D. Smith、Michael F. Greaney

  DOI：10.1021/ol402225d

  日期：2013.9.20

  A mild method for regioselective formation of 1,5-substituted 1,2,3-triazoles is described. The zinc-mediated reaction works at room temperature and is successful across a wide range of azido/alkynyl substrates. Additionally, the triazole 4-position can be further functionalized through the intermediate aryl-zinc to accommodate a diverse three-component coupling strategy.
• An Organocatalytic Regiospecific Synthesis of 1,5-Disubstituted 4-Thio-1,2,3-triazoles and 1,5-Disubstituted 1,2,3-Triazoles
  作者：Dhevalapally B. Ramachary、Patoju M. Krishna、Jagjeet Gujral、G. Surendra Reddy

  DOI：10.1002/chem.201503302

  日期：2015.11.16

  AbstractOrganocatalytic azide–ketone [3+2] cycloaddition (OrgAKC) of a variety of 1‐aryl‐2‐(arylthio)ethanones and 1‐alkyl‐2‐(alkylthio)ethanones with different aryl or alkyl azides is reported in dimethyl sulfoxide or solvent‐free under ambient conditions to furnish 1,5‐disubstituted 4‐thio‐1,2,3‐triazoles in a regiospecific manner, which are further converted into useful 1,5‐disubstituted 1,2,3‐triazoles by treatment with Raney Ni at 25 °C for 1–3 h. Notable features of the OrgAKC reaction include high rate and selectivity, solvent‐free conditions, easily available substrates and catalysts, a wide range of synthetic and medicinal applications, and excellent yields generating a vast library of triazoles.
• 一种含三氮唑青霉素分子的合成方法及其应用
  申请人：海南医学院

  公开号：CN115894522A

  公开（公告）日：2023-04-04

  本发明公开了一种含三氮唑青霉素分子的合成方法及其应用，对6－氨基青霉烷酸上羧基进行保护后合成化合物CX‑1或/和化合物CX‑2或/和化合物CX‑3，本发明制得的含有三氮唑的青霉素分子对β‑内酰胺酶具有明显的抑制作用。