N,N-dimethyl-N'-(2,4,6-trinitrobenzylidene)benzene-1,4-diamine | 26977-78-6

• 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: N,N-dimethyl-N'-(2,4,6-trinitrobenzylidene)benzene-1,4-diamine
• 英文别名: 2,4,6-trinitrobenzaldehyde 4-(dimethylamino)phenylimine；N-(2',4',6'-trinitrobenzylidene)-4-dimethylaminoaniline；N,N-dimethyl-N'-(2,4,6-trinitro-benzylidene)-p-phenylenediamine；N,N-Dimethyl-N'-(2,4,6-trinitro-benzyliden)-p-phenylendiamin；2.4.6-Trinitro-benzaldehyd-(4-dimethylamino-phenylimin)；N.N-Dimethyl-N'-(2.4.6-trinitro-benzal)-p-phenylendiamin；N,N-dimethyl-4-[(2,4,6-trinitrophenyl)methylideneamino]aniline
• CAS: 26977-78-6
• 化学式: C₁₅H₁₃N₅O₆
• 分子量: 359.298
• InChiKey: ZXAOZUWVYGEAIT-UHFFFAOYSA-N

物化性质

• 熔点：
  218-219 °C(Solv: N,N-dimethylformamide (68-12-2))
• 沸点：
  540.6±50.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  153
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-N'-(2,4,6-trinitrobenzylidene)benzene-1,4-diamine 在 盐酸 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 27.0h， 生成 4,6-dinitro-1-phenyl-1H-indazole
  参考文献：
  名称：

  Regiospecificity of nucleophilic substitution in 4,6-dinitro-1-phenyl-1H-indazole

  摘要：

  The reactions of 4,6-dinitro-1-phenyl-1H-indazole with anionic nucleophiles RS- and N-3(-) lead to the regiospecific replacement of the nitro group at position 4. The reaction with N2H4 . H2O + FeCl3 also results in reduction of only the 4-NO2 group. Based on this fact, a procedure was developed for the preparation of previously unknown 3-unsubstituted 4-X-6-nitro-1-phenyl-1H-indazoles (X is a residue of a nucleophile or NH2). Comparison of the data on the selective nucleophilic substitution (4-NO2 group) in 3-Z-1-aryl-4,6-dinitro-1H-indazoles shows that in the case of Z = H, the regiospecificity of substitution is determined by the electronic effect of the annelated pyrazole ring.

  DOI：

  10.1023/b:rucb.0000035642.41056.81
• 作为产物：
  描述：

  2,4,6-三硝基甲苯 、 alkaline earth salt of/the/ methylsulfuric acid 在 甲醇 、 potassium carbonate 作用下， 生成 N,N-dimethyl-N'-(2,4,6-trinitrobenzylidene)benzene-1,4-diamine
  参考文献：
  名称：

  McGookin, Journal of Applied Chemistry, 1955, vol. 5, p. 65

  摘要：

  DOI：

文献信息

• Synthetic Utilization of Polynitroaromatic Compounds. 1. S-Derivatization of 1-Substituted 2,4,6-Trinitrobenzenes with Thiols
  作者：G. Zlotin、G. Kislitsin、V. Samet、A. Serebryakov、D. Konyushkin、V. V. Semenov、A. C. Buchanan III and、A. A. Gakh

  DOI：10.1021/jo000479d

  日期：2000.12.1

  Reactions of 1-R-2,4,6-trinitrobenenes (R = alkyl, protected aldehyde, aminocarbonyl, cyano groups, or isoxazole ring) with thiol salts were investigated. In most cases, these reactions gave a mixture of minor para and major ortho substitution products. Reactions of N,N-disubstituted 2,4,6-trinitrobenzamides with S-,O-, and N-nucleophiles afforded products of substitution of the p-nitro group exclusively

  研究了1-R-2,4,6-三硝基苯（R =烷基，受保护的醛，氨基羰基，氰基或异恶唑环）与硫醇盐的反应。在大多数情况下，这些反应产生少量的对位和主要的邻位取代产物。N，N-二取代的2,4,6-三硝基苯甲酰胺与S-，O-和N-亲核试剂的反应仅提供了对硝基取代的产物。发现1-氰基-2,4,6-三硝基苯具有最高的反应性和最低的选择性：所有三个硝基都可以使用过量的硫醇盐取代。2-R-4，6-二硝基苯甲酰胺在相似条件下无区域选择性，可生成对位和邻位异构体的1：1混合物。
• Synthesis and characterization of new energetic derivatives containing a high nitrogen content moiety and picryl group: a new strategy for incorporating the picryl functionality
  作者：Bo Wu、Hongwei Yang、Zhixin Wang、Qiuhan Lin、Xuehai Ju、Chunxu Lu、Guangbin Cheng

  DOI：10.1039/c4ra08084j

  日期：——

  The synthesis of new picryl derivatives containing a high nitrogen content moiety from new starting materials are reported.

  报道了利用新的起始材料合成含有高氮含量基团的新型硝化苯酚衍生物的方法。
• Polyphasic Characterization of Poly-3-hydroxybutyrate-co-3-hydroxyvalerate (P(HB-co-HV)) Metabolizing and Denitrifying Acidovorax sp. Strains
  作者：K. Schloe、M. Gillis、B. Hoste、B. Pot、M. Vancanneyt、J. Mergaert、J. Swings、J. Biedermann、R. Süssmuth

  DOI：10.1016/s0723-2020(00)80066-1

  日期：2000.10

  For the purpose of denitrification in small drinking water plants, a bacterial mixed population was isolated from a packed bed column bioreactor with poly-3-hydroxybutyrate-co-3-hydroxyvalerate (P(HB-co-HV)) as a substrate for the denitrification of ground water (10 degreesC). Isolates 2nIII from the mixed culture, with the ability to denitrify and metabolize P(HB-co-HV), were used as starter cultures for the elimination of nitrate in ground water. The strains were characterized by diverse techniques. Classical phenotypic studies lead to rRNA group III of the genus Pseudomonas. Results obtained by molecular techniques demonstrated that the 2nIII strains are members of the Comamonadaceae and shows similarities to the genus Acidovorax. However, an integration of the 2nIII isolates within one of the known Acidovorax species is not possible for the moment. The 2nIII starter cultures clustered close to Av. temperans according to their whole cell proteins and fatty acids, whereas in DNA/DNA hybridization no significant DNA binding (< 25%) was found. In contrast a significant but low degree of: DNA/DNA hybridization was found between the 2nIII st rains and Av. facilis and Ar,. delafieldii. Our polyphasic results lead to the conclusion that the 2nIII strains may constitute a separate Acicdovorax species.
• McGookin, Journal of Applied Chemistry, 1955, vol. 5, p. 65
  作者：McGookin

  DOI：——

  日期：——
• Sachs; Everding, Chemische Berichte, 1903, vol. 36, p. 961
  作者：Sachs、Everding

  DOI：——

  日期：——