(E)-4-(1-phenyl-1H-1,2,3-triazol-4-yl)butan-3-ene-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (E)-4-(1-phenyl-1H-1,2,3-triazol-4-yl)butan-3-ene-2-one
• 英文别名: 4-(1-phenyl-1H-1,2,3-triazol-4-yl)but-3-en-2-one；(E)-4-(1-phenyltriazol-4-yl)but-3-en-2-one
• 化学式: C₁₂H₁₁N₃O
• 分子量: 213.239
• InChiKey: OSUONZBXQTUVDL-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  5-甲基-2-呋喃甲醇 、 叠氮苯 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以70%的产率得到(E)-4-(1-phenyl-1H-1,2,3-triazol-4-yl)butan-3-ene-2-one
  参考文献：
  名称：

  Conversion of 2-Furylcarbinols with Alkyl or Aryl Azides to Highly Functionalized 1,2,3-Triazoles via Cascade Formal [3 + 2] Cycloaddition/Ring-Opening

  摘要：

  A Lewis acid promoted cascade cycloaddition/ring-opening of 2-furylcarbinols with alkyl or aryl azides is described. The reaction features an initial formal [3 + 2] cycloaddition to form a trisubstitued triazole motif, followed by a ring opening of furan to generate the (E)-configuration of the enone. A wide range of highly functionalized triazoles is expediently and efficiently synthesized in a highly step-economical manner.

  DOI：

  10.1021/ol502437y

文献信息

• Conversion of 2-Furylcarbinols with Alkyl or Aryl Azides to Highly Functionalized 1,2,3-Triazoles via Cascade Formal [3 + 2] Cycloaddition/Ring-Opening
  作者：Jiawei Guo、Binxun Yu、Ya-Nan Wang、Dongyu Duan、Li-Li Ren、Ziwei Gao、Jing Gou

  DOI：10.1021/ol502437y

  日期：2014.10.3

  A Lewis acid promoted cascade cycloaddition/ring-opening of 2-furylcarbinols with alkyl or aryl azides is described. The reaction features an initial formal [3 + 2] cycloaddition to form a trisubstitued triazole motif, followed by a ring opening of furan to generate the (E)-configuration of the enone. A wide range of highly functionalized triazoles is expediently and efficiently synthesized in a highly step-economical manner.