N-(4,9-dioxo-4,9-dihydro-2H-naphtho[2,3-d][1,2,3]triazol-2-yl)-diacetamide | 3915-97-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(4,9-dioxo-4,9-dihydro-2H-naphtho[2,3-d][1,2,3]triazol-2-yl)-diacetamide
• 英文别名: N-acetyl-N-(4,9-dioxobenzo[f]benzotriazol-2-yl)acetamide
• CAS: 3915-97-7
• 化学式: C₁₄H₁₀N₄O₄
• 分子量: 298.258
• InChiKey: OXHHRUSWVJUTGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(triphenylphosphanylideneamino)naphtho-1,2,3-triazole-4,9-dione 在 盐酸 、 硫酸 作用下， 以 溶剂黄146 为溶剂， 反应 4.17h， 生成 N-(4,9-dioxo-4,9-dihydro-2H-naphtho[2,3-d][1,2,3]triazol-2-yl)-diacetamide
  参考文献：
  名称：

  Synthesis of 2-Amino-1,2,3-triazole Derivatives from Vicinal Diazides

  摘要：

  Triphenylphosphine reacts with naphthoquinone diazide to form almost quantitatively the phosphorane of a unique 2-amino-1,2,3-triazole derivative. This compound undergoes an aza-Wittig reaction with aldehydes and is readily hydrolyzed to the free 2-amino-1,2,3-triazole. The free amine reacts normally with acids and aldehydes, The 2-amino-1,2,3-triazole system is stable and high melting, and most derivatives give the parent ion as the largest peak in the mass spectrum. The compounds absorb at 300-350 nm with a strong emission in the range 500-700 nm, depending upon the substituents. Cyclic voltammetry shows one reversible, single-electron reduction wave.

  DOI：

  10.1021/jo970197m

文献信息

• 2-Amino-1,2,3-triazole derivatives fromvicinal diazides
  作者：Duoli Sun、Mariusz Krawiec、Charles F. Campana、William H. Watson

  DOI：10.1007/bf02576456

  日期：1997.10

  A unique 2-amino-1,2,3-triazole system has been synthesized by the reaction of a vicinal diazide with triphenylphosphine. The crystal structures of five 2-amino-1,2,3-triazole systems, a ditetrazole and a Staudinger adduct are reported. Ab initio calculations are used to rationalize the structures and properties of these materials, and possible reaction pathways are discussed.
• Synthesis of 2-Amino-1,2,3-triazole Derivatives from Vicinal Diazides
  作者：Duoli Sun、William H. Watson

  DOI：10.1021/jo970197m

  日期：1997.6.13

  Triphenylphosphine reacts with naphthoquinone diazide to form almost quantitatively the phosphorane of a unique 2-amino-1,2,3-triazole derivative. This compound undergoes an aza-Wittig reaction with aldehydes and is readily hydrolyzed to the free 2-amino-1,2,3-triazole. The free amine reacts normally with acids and aldehydes, The 2-amino-1,2,3-triazole system is stable and high melting, and most derivatives give the parent ion as the largest peak in the mass spectrum. The compounds absorb at 300-350 nm with a strong emission in the range 500-700 nm, depending upon the substituents. Cyclic voltammetry shows one reversible, single-electron reduction wave.