(1-(4-nitrobenzyl)-1H-1,2,3-triazol-4-yl)(phenyl)methanone | 153897-53-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1-(4-nitrobenzyl)-1H-1,2,3-triazol-4-yl)(phenyl)methanone
• 英文别名: [1-[(4-Nitrophenyl)methyl]triazol-4-yl]-phenylmethanone
• CAS: 153897-53-1
• 化学式: C₁₆H₁₂N₄O₃
• 分子量: 308.296
• InChiKey: ICUIKRWXSMKWBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  93.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯甲酰氯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 silver fluoride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 13.5h， 生成 (1-(4-nitrobenzyl)-1H-1,2,3-triazol-4-yl)(phenyl)methanone
  参考文献：
  名称：

  An efficient and high-yielding one-pot synthesis of 4-acyl-1,2,3-triazoles via triisopropylsilyl-protected ynones

  摘要：

  A practical and efficient process has been developed for the synthesis of 1-substituted 4-acyl-1H-1,2,3-triazoles using a three-step one-pot synthetic approach. This transformation involves an initial preparation of triisopropylsilyl (TIPS)-protected ynones from acid chlorides and TIPS-acetylene, followed by a AgF-mediated TIPS deprotection and Cu-catalyzed Huisgen cycloaddition. The increased chemical stability of TIPS-protected ynones was an important factor in the high overall product yield. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.025

文献信息

• An efficient and high-yielding one-pot synthesis of 4-acyl-1,2,3-triazoles via triisopropylsilyl-protected ynones
  作者：Soonho Hwang、Hoon Bae、Sumin Kim、Sanghee Kim

  DOI：10.1016/j.tet.2011.12.025

  日期：2012.2

  A practical and efficient process has been developed for the synthesis of 1-substituted 4-acyl-1H-1,2,3-triazoles using a three-step one-pot synthetic approach. This transformation involves an initial preparation of triisopropylsilyl (TIPS)-protected ynones from acid chlorides and TIPS-acetylene, followed by a AgF-mediated TIPS deprotection and Cu-catalyzed Huisgen cycloaddition. The increased chemical stability of TIPS-protected ynones was an important factor in the high overall product yield. (C) 2011 Elsevier Ltd. All rights reserved.