2,5-diphenylamino-3,6-dibromo-1,4-benzoquinone | 15080-56-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-diphenylamino-3,6-dibromo-1,4-benzoquinone
• 英文别名: 2,5-dianilino-3,6-dibromo-1,4-benzoquinone；2,5-dianilino-3,6-dibromo-[1,4]benzoquinone；2,5-Dianilino-3,6-dibrom-[1,4]benzochinon；3.6-Dibrom-2.5-dianilino-p-chinon；2,5-Dianilino-3,6-dibromocyclohexa-2,5-diene-1,4-dione
• CAS: 15080-56-5
• 化学式: C₁₈H₁₂Br₂N₂O₂
• 分子量: 448.113
• InChiKey: SIHXJQMPAMPGDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5-diphenylamino-3,6-dibromo-1,4-benzoquinone 在 sodium hydroxide 作用下， 生成 2,5-dianilino-3,6-dihydroxy-[1,4]benzoquinone
  参考文献：
  名称：

  The Action of Alkali on Dianilinodibromobenzoquinone

  摘要：

  DOI：

  10.1021/ja01318a047
• 作为产物：
  描述：

  苯酚 在 水 、 溴 、 碘 、 苯 作用下， 生成 2,5-diphenylamino-3,6-dibromo-1,4-benzoquinone
  参考文献：
  名称：

  Stenhouse, Justus Liebigs Annalen der Chemie, 1872, vol. Suppl.8, p. 20

  摘要：

  DOI：

文献信息

• Reaction of Amidine Phenylogous with<i>p</i>-Benzoquinones
  作者：Ahmed M. Nour El-Din、Aboul-Fetouh E. Mourad、Alaa A. Hassan、Mohsen A. Gomaa

  DOI：10.1246/bcsj.64.1966

  日期：1991.6

  N-(4-Dimethylaminobenzylidene)anilines and N1-(4-dimethylaminophenyl)-N1,N2-diphenylformamidine reacted with tetrachloro-, tetrabromo,- and tetrafluoro-p-benzoquinones via charge-transfer complexes formation giving 2-monoarylamino-3,5,6-trihalo-p-benzoquinones and 2,5-bis(arylamino)-3,6-dihalo-p-benzoquinones. The course of the reaction leading to the formation of the products has been interpreted.

  N-(4-二甲氨基亚苄基)苯胺和 N1-(4-二甲氨基苯基)-N1,N2-二苯基甲脒与四氯、四溴和四氟对苯醌通过电荷转移络合物的形成发生反应，生成 2-单芳基氨基-3,5,6-三卤对苯醌和 2,5-双(芳基氨基)-3,6-二卤对苯醌。对生成产物的反应过程进行了解释。
• Synthesis of [1,4]benzoxazino[2,3-b]phenoxazines and [1,4]benzothiazino[2,3-b]phenothiazines
  作者：R. L. Mital、S. K. Jain

  DOI：10.1039/j39710001875

  日期：——

  A number of substituted 6,13-dihalogenotriphenodioxazines have been synthesised (a) by condensing halogeno-p-benzoquinones with arylamines followed by cyclisation of the resulting bisarylamino-quinones with benzoyl chloride in nitrobenzene and (b) by condensing halogeno-p-benzoquinones with o-aminophenols in the presence of anhydrous sodium acetate in an alcoholic medium. A few triphenodithiazines

  已经合成了许多取代的6,13-​​二卤代三苯并二恶嗪（a）通过将卤代对苯甲醌与芳胺缩合，然后将生成的双芳基氨基苯醌与苯甲酰氯在硝基苯中环化，以及（b）通过将卤代对苯甲醌与苯甲酰氯缩合而合成。在无水乙酸钠存在下，在酒精介质中邻氨基苯酚。已经通过将邻氨基苯硫醇锌锌与卤代对苯醌醌缩合制备了一些三苯并二噻嗪。
• Electronic Effects of Ligand Substitution on Spin Crossover in a Series of Diiminoquinonoid-Bridged Fe^II₂ Complexes
  作者：Jesse G. Park、Ie-Rang Jeon、T. David Harris

  DOI：10.1021/ic5025586

  日期：2015.1.5

  A series of four isostructural Fe-2(II) complexes, [(TPyA)(2)Fe-2(XL)](2)(+) (TPyA = tris(2-pyridylmethyl)amine; XL2- = doubly deprotonated form of 3,6-disubstituted-2,5-dianilino-1,4-benzoquinone; X = H, Br, Cl, and F), were synthesized to enable a systematic study of electronic effects on spin crossover behavior. Comparison of X-ray diffraction data for these complexes reveals the sole presence of high-spin Fe-II at 225 K and mixtures of high-spin and low-spin Fe-II at 100 K, which is indicative of incomplete spin crossover. In addition, crystal packing diagrams show that these complexes are well-isolated from one another in the solid state, owing primarily to the presence of bulky tetra(aryl)borate counteranions, such that spin crossover is likely not significantly affected by intermolecular interactions. Variable-temperature dc magnetic susceptibility data confirm the structural observations and reveal that 54(1), 56(1), 62(1), and 84(1)% of Fe-II centers remain high-spin even below 65 K. Moreover, fits to magnetic data provide crossover temperatures of T-1/2 = 160(1), 124(1), 121(1), and 110(1) K for X = H, Br, Cl, and F, respectively, along with enthalpies of Delta H = 11.4(3), 8.5(3), 8.3(3), and 7.5(2) kJ/mol, respectively. These parameters decrease with increasing electronegativity of X and thus increasing electron-withdrawing character of L-X(2-), suggesting that the observed trends originate primarily from inductive effects of X. Moreover, when plotted as a function of the Pauling electronegativity of X, both T-1/2 and Delta H undergo a linear decrease. Further analyses of the low-temperature magnetic data and variable-temperature Mossbauer spectroscopy suggest that the incomplete spin crossover behavior in [(TPyA)(2)Fe-2(XL)](2+) is best described as a transition from purely [Fe-HS-Fe-HS] (HS = high-spin) complexes at high temperature to a mixture of [Fe-HS-Fe-HS] and [Fe-HS-Fe-LS] (LS = low-spin) complexes at low temperature, with the number of [Fe-HS-Fe-HS] species increasing with decreasing electron-withdrawing character of L-X(2-).
• SYNTHESIS OF SOME NEW PYRROLO-(2,3-f)BENZOPYRROL-4,8-DIONE DERIVATIVES
  作者：A. M. Soliman、A. M. El-Saghier

  DOI：10.1081/scc-100104466

  日期：2001.1.1

  Some new functionally substituted pyrrolobenzopyrrole derivatives were obtained starting with 3,6-diamino-2,5-dibromo-1,4-benzoquinone derivatives and active methylene reagents.
• Stenhouse, Justus Liebigs Annalen der Chemie, 1872, vol. Suppl.8, p. 20
  作者：Stenhouse

  DOI：——

  日期：——