1,3,4,6-tetraphenyl-1,2,4,5-tetraaza-2,5-hexadiene | 1527-92-0

• 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: 1,3,4,6-tetraphenyl-1,2,4,5-tetraaza-2,5-hexadiene
• 英文别名: 1,4-diphenyl-2-benzylidenebenzhydrazidine；N^α,N^β'-Diphenyl-N^β-benzyliden-benzhydrazidin；N'-anilino-N-(benzylideneamino)-N-phenylbenzenecarboximidamide
• CAS: 1527-92-0
• 化学式: C₂₆H₂₂N₄
• 分子量: 390.487
• InChiKey: FJCPBNXVJQBWAU-UHFFFAOYSA-N

物化性质

• 熔点：
  202 °C
• 沸点：
  545.7±33.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3,4,6-tetraphenyl-1,2,4,5-tetraaza-2,5-hexadiene 在 copper(II) acetate monohydrate 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以61 mg的产率得到1,3,5-三苯基-1,2,4-三唑
  参考文献：
  名称：

  Copper(II)-Catalyzed Aerobic Oxidative Synthesis of Substituted 1,2,3- and 1,2,4-Triazoles from Bisarylhydrazones via C–H Functionalization/C–C/N–N/C–N Bonds Formation

  摘要：

  An unprecedented copper(II)-catalyzed aerobic oxidative synthesis of 2,4,5-triary1-1,2,3-triazoles and 1,3,5-triaryl-1,2,4-triazoles from bisarylhydrazones as the common starting precursor has been achieved via cascade C-H functionalization/C-C/N-N/C-N bonds formation under mild reaction conditions. One of the enthralling outcomes of this strategy is the copper(II)-catalyzed room temperature C-H functionalization/C-N bond formation in presence of air, which has been accomplished during the synthesis of substituted 1,2,4-triazoles. This new class of compounds could give prospective luminescence as an iconic component in the area of pharmaceutical and biological sciences. The intermediates for both the processes have been isolated to elucidate the mechanistic scenario.

  DOI：

  10.1021/jo300592t
• 作为产物：
  描述：

  苯甲醛苯腙 在 三乙烯二胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 30.0h， 生成 1,3,4,6-tetraphenyl-1,2,4,5-tetraaza-2,5-hexadiene
  参考文献：
  名称：

  Copper(II)-Catalyzed Aerobic Oxidative Synthesis of Substituted 1,2,3- and 1,2,4-Triazoles from Bisarylhydrazones via C–H Functionalization/C–C/N–N/C–N Bonds Formation

  摘要：

  An unprecedented copper(II)-catalyzed aerobic oxidative synthesis of 2,4,5-triary1-1,2,3-triazoles and 1,3,5-triaryl-1,2,4-triazoles from bisarylhydrazones as the common starting precursor has been achieved via cascade C-H functionalization/C-C/N-N/C-N bonds formation under mild reaction conditions. One of the enthralling outcomes of this strategy is the copper(II)-catalyzed room temperature C-H functionalization/C-N bond formation in presence of air, which has been accomplished during the synthesis of substituted 1,2,4-triazoles. This new class of compounds could give prospective luminescence as an iconic component in the area of pharmaceutical and biological sciences. The intermediates for both the processes have been isolated to elucidate the mechanistic scenario.

  DOI：

  10.1021/jo300592t

文献信息

• Reaction of allyl phenylcarbamate with benzaldehyde phenylhydrazones in the presence of N-chlorobenzenesulfonamide sodium salt
  作者：A. V. Velikorodov

  DOI：10.1007/s11178-005-0047-8

  日期：2004.10

  Phenylhydrazones derived from 4-bromo-, 4-methoxy-, and 3-nitrobenzaldehydes react with allyl phenylcarbamate in the presence of N-chlorobenzenesulfonamide sodium salt to give the corresponding 3-aryl-1-phenyl-5-(phenylcarbamoyloxymethyl)-4,5-dihydro-1H-pyrazoles whose structure was confirmed by the IR and 1H and 13C NMR spectra.

  由 4-溴-、4-甲氧基-和 3-硝基苯甲酰肼衍生出的苯肼在 N-氯苯磺酰胺钠盐存在下与苯基氨基甲酸烯丙基酯发生反应，生成相应的 3-芳基-1-苯基-5-（苯基氨基甲酰氧甲基）-4,5-二氢-1H-吡唑，其结构由红外光谱、1H 和 13C NMR 光谱证实。
• Minunni, Gazzetta Chimica Italiana, 1897, vol. 27 II, p. 267
  作者：Minunni

  DOI：——

  日期：——
• Barton,D.H.R. et al., Journal of the Chemical Society. Perkin transactions I, 1976, p. 38 - 42
  作者：Barton,D.H.R. et al.

  DOI：——

  日期：——
• Reaction of 1,3-diphenylnitrilimine with benzaldehyde phenylhydrazone
  作者：B. I. Buzykin、N. G. Gazetdinova

  DOI：10.1007/bf00949175

  日期：1980.7
• Reaction 5-(Arylmethylidene)-2,4,6-pyrimidine-2,4,6(1H,3H,5H)-triones with Arenecarbaldehyde Phenylhydrazones in the Presence of Sodium N-Chlorobenzenesulfonamide
  作者：A. G. Tyrkov、E. A. Yurtaeva、O. B. Rsaeva

  DOI：10.1134/s1070428019020222

  日期：2019.2

  The reactions of 5-(arylmethylidene)-2,4,6-pyrimidine-2,4,6(1H,3H,5H)-triones with arenecarbaldehyde phenylhydrazones in the presence of sodium N-chlorobenzenesulfonamide give 2,3,7,9-tetraasaspiro-[4.5]dec-1-ene-6,8,10-triones in yields of 30-45%.