2-amino-2-hydrobenzo[f]benzotriazole-4,6-dione | 3763-32-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-amino-2-hydrobenzo[f]benzotriazole-4,6-dione
• 英文别名: 2-amino-2H-naphtho[2,3-d][1,2,3]triazole-4,9-dione；2-Aminobenzo[f]benzotriazole-4,9-dione
• CAS: 3763-32-4
• 化学式: C₁₀H₆N₄O₂
• 分子量: 214.183
• InChiKey: ZYKIKQNGEIRSJF-UHFFFAOYSA-N

物化性质

• 熔点：
  313-314 °C (decomp)
• 沸点：
  513.7±53.0 °C(Predicted)
• 密度：
  1.79±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-二乙基-4-氨基苯甲醛 、 2-amino-2-hydrobenzo[f]benzotriazole-4,6-dione 以 甲醇 为溶剂， 以78%的产率得到2-[1-aza-2-(4-(diethylamino)phenyl)vinyl]-2-hydrobenzo[f]benzotriazole-4,9-dione
  参考文献：
  名称：

  摘要：

  A series of phenyldialkylamine, dimethoxyphenyl, and nitrothiophene derivatives of 2-amino-1,2,3-triazolequinones was characterized by NMR, IR, mass spectroscopy, cyclic voltammetry, and chemical analyses. The solvatochromic procedure was used to evaluate the potential of nine compounds for nonlinear optical applications, and the possible failure of this model is discussed. The crystal structures of seven compounds were determined: (4) P2(1)/c, a = 15.430(3) Angstrom, b = 7.633(2) Angstrom, c = 15.940(3) Angstrom, beta = 105.19(3)degrees; (5) P2(1)/c, a = 20.201(2) Angstrom, b = 9.6579(9) Angstrom, c = 18.517(2) Angstrom, beta = 95.907(2)degrees; (6) P-1, a = 7.769(2) Angstrom, b = 8.515(3) Angstrom, c = 17.312(5) Angstrom, alpha = 89.347(7)degrees; beta = 83.219(6)degrees, gamma = 86.001(7)degrees; (7) P-1, a = 8.1365(7) Angstrom, b = 8.9605(8) Angstrom, c = 11.630(1) Angstrom, alpha = 79.553(2)degrees, beta = 75.048(2)degrees, gamma = 82.080(2)degrees; (8) P-1, a = 8.298(3) Angstrom, b = 9.720(3) Angstrom, c = 10.033(3) Angstrom, alpha = 84.803(6)degrees, beta = 83.735(6)degrees, gamma = 77.659(5)degrees; (10) P2(1)/n, a = 8.4300(7) Angstrom, b = 13.980(1) Angstrom, c = 13.975(1) Angstrom, beta = 106.590(2)degrees; (12) P2(1)/n, a = 7.715(2) Angstrom, b = 14.206(3) Angstrom, c = 12.758(3) Angstrom, beta = 91.016(5)degrees.

  DOI：

  10.1023/a:1014399201800
• 作为产物：
  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

文献信息

• ——
  作者：Satish G. Bodige、Miguel Mendez-Rojas、William H. Watson

  DOI：10.1023/a:1009582129822

  日期：——

  The syntheses and structure of 2-triarylphosphoranimine-1,2,3-triazole derivatives from vicinal diazides have been investigated. Compounds derived from dichloronapththoquinone, 2,3-dichloro-5,6-dimethylbenzoquinone, and 2,3,5,6-tetrachlorobenzoquinone are included. X-ray structures, NMR, IR, UV, and cyclic voltammetry data are reported. Compound 2 crystallizes in space group P (1) over bar with a = 12.31(1), b = 12.469(3), c = 10.088(3) Angstrom, alpha = 97.19(3), beta = 103.79(6), gamma = 101.84(4)degrees and D-calc = 1.466 g/cm for Z = 2. Compound 4 crystallizes in space group P2(1)/c with a = 9.044(2), b = 10.882(2), c = 19.110(4) Angstrom, beta = 99.06(2)degrees, and D-calc = 1.324 g/cm for Z = 2. Compound 6 crystallizes in space group P2(1)/a with a = 8.85(1), b = 14.841(8), c = 11.372(8) Angstrom, beta = 107.19(3)degrees and D-calc = 1.397 g/cm for Z = 4. Compound 11 crystallizes in space group P2(1)/n with a = 8.823(3), b = 16.501(6), c = 16.221(3) Angstrom, beta = 103.58(2)degrees and D-calc = 1.309 g/cm for Z = 4. Compound 12 crystallizes in space group P (1) over bar with a = 11.606(8), b = 11.671(5), c = 10.734(3) Angstrom, alpha = 101.62(3), beta = 93.70(4), gamma = 64.33(4)degrees, and D-calc = 1.438 g/cm for Z = 2. Compound 13 crystallizes in space group C2/c with a = 13.337(7), b = 9.217(6), c = 24.78(1) Angstrom, beta = 102.85(5)degrees, and D-calc = 1.478 g/cm for Z = 8.
• 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.
• ——
  作者：Miguel A. Mendez-Rojas、Satish G. Bodige、Krzysztof Ejsmont、William H. Watson

  DOI：10.1023/a:1014399201800

  日期：——

  A series of phenyldialkylamine, dimethoxyphenyl, and nitrothiophene derivatives of 2-amino-1,2,3-triazolequinones was characterized by NMR, IR, mass spectroscopy, cyclic voltammetry, and chemical analyses. The solvatochromic procedure was used to evaluate the potential of nine compounds for nonlinear optical applications, and the possible failure of this model is discussed. The crystal structures of seven compounds were determined: (4) P2(1)/c, a = 15.430(3) Angstrom, b = 7.633(2) Angstrom, c = 15.940(3) Angstrom, beta = 105.19(3)degrees; (5) P2(1)/c, a = 20.201(2) Angstrom, b = 9.6579(9) Angstrom, c = 18.517(2) Angstrom, beta = 95.907(2)degrees; (6) P-1, a = 7.769(2) Angstrom, b = 8.515(3) Angstrom, c = 17.312(5) Angstrom, alpha = 89.347(7)degrees; beta = 83.219(6)degrees, gamma = 86.001(7)degrees; (7) P-1, a = 8.1365(7) Angstrom, b = 8.9605(8) Angstrom, c = 11.630(1) Angstrom, alpha = 79.553(2)degrees, beta = 75.048(2)degrees, gamma = 82.080(2)degrees; (8) P-1, a = 8.298(3) Angstrom, b = 9.720(3) Angstrom, c = 10.033(3) Angstrom, alpha = 84.803(6)degrees, beta = 83.735(6)degrees, gamma = 77.659(5)degrees; (10) P2(1)/n, a = 8.4300(7) Angstrom, b = 13.980(1) Angstrom, c = 13.975(1) Angstrom, beta = 106.590(2)degrees; (12) P2(1)/n, a = 7.715(2) Angstrom, b = 14.206(3) Angstrom, c = 12.758(3) Angstrom, beta = 91.016(5)degrees.
• 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.