2-(triphenylphosphanylideneamino)naphtho-1,2,3-triazole-4,9-dione | 3829-73-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(triphenylphosphanylideneamino)naphtho-1,2,3-triazole-4,9-dione
• 英文别名: 2-(triphenyl-λ⁵-phosphanylideneamino)-2H-naphtho[2,3-d][1,2,3]triazole-4,9-dione；2-((Triphenylphosphoranylidene)amino)-2H-naphtho(2,3-D)(1,2,3)triazole-4,9-dione；2-[(triphenyl-λ5-phosphanylidene)amino]benzo[f]benzotriazole-4,9-dione
• CAS: 3829-73-0
• 化学式: C₂₈H₁₉N₄O₂P
• 分子量: 474.458
• InChiKey: XONJZGJIDPJWQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(triphenylphosphanylideneamino)naphtho-1,2,3-triazole-4,9-dione 在 盐酸 作用下， 反应 4.0h， 以43%的产率得到2-amino-2-hydrobenzo[f]benzotriazole-4,6-dione
  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
• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 在 sodium azide 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 2-(triphenylphosphanylideneamino)naphtho-1,2,3-triazole-4,9-dione
  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

• Synthesis and Optical Nonlinearities of a 2-Amino-1,2,3-triazolquinone Derivative
  作者：G. Ramos-Ortiz、S. Romero-Servin、J. L. Maldonado、M. A. Meneses-Nava、O. Barbosa-García、P. Zapata Castillo、M. A. Méndez-Rojas、Herbert Höpfl

  DOI：10.1080/15421400903291228

  日期：2009.12.7

  We report on the synthesis and nonlinear optical characterization of a novel 2-amino-1,2,3-triazolquinone derivative, namely, 2-(yliminopropylphenyl-N,N'-dimethylamino)naphto-1,2,3-triazole-4,9-dione (ATZQ). The second-order nonlinear optical properties in solution were characterized using the hyper-Rayleigh scattering (HRS) technique, while the third-order nonlinearities of ATZQ-doped polymer films were measured through the use of the THG-Maker fringes technique. These experiments showed that this compound exhibits large second- and third-order nonlinear effects at the molecular level, with a first hyperpolarizability constant of 834x10-30esu at 1064nm and a second hyperpolarizability constant of 3.5x10-33esu at the telecommunication wavelength range of 1200-1700nm.
• 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.