3-(4-phenyl-1,2,3-triazol-1-yl)-cyclopentanone | 1115931-99-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-phenyl-1,2,3-triazol-1-yl)-cyclopentanone
• 英文别名: 3-(4-Phenyltriazol-1-yl)cyclopentan-1-one
• CAS: 1115931-99-1
• 化学式: C₁₃H₁₃N₃O
• 分子量: 227.266
• InChiKey: KGKWCGYBROPHIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-苯基-1,2,3-三氮唑 、 2-环戊烯酮 在 cerium(III) chloride heptahydrate 、 silica gel 、 sodium iodide 作用下， 以 neat (no solvent) 为溶剂， 反应 18.0h， 以78%的产率得到3-(4-phenyl-1,2,3-triazol-1-yl)-cyclopentanone
  参考文献：
  名称：

  CeCl₃·7H₂O-NaI-SiO₂Catalyzed Aza-Michael Addition of N-Heterocycles to Enones under Solvent Free Conditions

  摘要：

  DOI：

  10.5012/bkcs.2012.33.11.3535

文献信息

• DABCO-mediated aza-Michael addition of 4-aryl-1H-1,2,3-triazoles to cycloalkenones. Regioselective synthesis of disubstituted 1,2,3-triazoles
  作者：Ujjawal Kumar Bhagat、Kamaluddin、Rama Krishna Peddinti

  DOI：10.1016/j.tetlet.2016.11.125

  日期：2017.1

  Aza-Michael addition of 4-aryl-1H-1,2,3-triazoles to 2-cycloalken-1-ones has been studied in the presence of DABCO as organic base. The reactions were carried out in acetonitrile at room temperature to provide 2,4-disubstituted 2H-1,2,3-triazoles as major adducts and 1,4-disubstituted 1H-1,2,3-triazoles as minor adducts. Though the reaction times are longer (4-8 days), the two regioisomers were separated by using column chromatography and the adducts were obtained in very good to excellent combined chemical yields. The electron-rich and electron-poor substituents on aryl moiety of 4-aryl-triazoles could tolerate the reaction conditions to afford the title adducts. (C) 2016 Elsevier Ltd. All rights reserved.