1,6-bis-p-chlorophenyl-3,4-dihydroxy-2,4-hexadiene-1,6-dione | 139266-59-4

• 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: 1,6-bis-p-chlorophenyl-3,4-dihydroxy-2,4-hexadiene-1,6-dione
• 英文别名: 3,4-dihydroxy-1,6-bis(p-chlorophenyl)-2,4-hexadien-1,6-dione
• CAS: 139266-59-4
• 化学式: C₁₈H₁₂Cl₂O₄
• 分子量: 363.197
• InChiKey: UAROJMZLVNTJFN-XFQWXJFMSA-N

物化性质

• 沸点：
  477.4±45.0 °C(Predicted)
• 密度：
  1.440±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.94
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,6-bis-p-chlorophenyl-3,4-dihydroxy-2,4-hexadiene-1,6-dione 在 吡啶 、 三氟乙酸酐 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以76%的产率得到5-(4-Chlorophenyl)-2-(2-(4-chlorophenyl)-2-oxoethylidene)-3(2H)-furanone
  参考文献：
  名称：

  1,3,4,6-tetracarbonyl compounds. 3. synthesis, structural features, and antimicrobial activity of 1,6-diaryl-3,4-dihydroxy-2,4-hexadiene-1,6-diones

  摘要：

  DOI：

  10.1007/bf02251994
• 作为产物：
  描述：

  5-(4-氯苯基)呋喃-2,3-二酮 在 N,N'-二硝基乙二胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以55%的产率得到1,6-bis-p-chlorophenyl-3,4-dihydroxy-2,4-hexadiene-1,6-dione
  参考文献：
  名称：

  1,3,4,6-Tetracarbonyl Compounds. I. The Novel Synthesis of 1,6-Diaryl-3,4-dihydroxy-hexa-2,4-diene-1,6-diones from 5-Aryl-furan-2,3-diones

  摘要：

  DOI：

  10.1002/prac.19933350813

文献信息

• 2,3-Bifunctionalized Quinoxalines: Synthesis, DNA Interactions and Evaluation of Anticancer, Anti-tuberculosis and Antifungal Activity
  作者：Michael Waring、Taibi Ben-Hadda、Ann Kotchevar、Abdelkrim Ramdani、Rachid Touzani、Sghir Elkadiri、Abdelkader Hakkou、Mohamed Bouakka、Tom Ellis

  DOI：10.3390/70800641

  日期：——

  A variety of 2,3-bifunctionalized quinoxalines (6-14) have been prepared by the condensation of 1,6-disubstituted-hexan-1,3,4,6-tetraones (1-4) with o-phenylenediamine, (R,R)-1,2-diaminocyclohexane and p-nitro-o-phenylenediamine. It is concluded that strong intramolecular N-H----O bonds in the favoured keto-enamine form may be responsible for the minimal biological activities observed in DNA footprinting, antitubercular, anti-fungal and anticancer tests with these hyper π-conjugated quinoxaline derivatives. However, subtle alteration by addition of a nitro group affecting the charge distribution confers significant improvements in biological effects and binding to DNA.

  通过 1,6-二取代己-1,3,4,6-四酮（1-4）与邻苯二胺、(R,R)-1,2-二氨基环己烷和对硝基邻苯二胺的缩合，制备了多种 2,3-双官能团喹喔啉（6-14）。研究得出的结论是，这些超π-共轭喹喔啉衍生物在 DNA 追踪、抗结核、抗真菌和抗癌试验中具有极低的生物活性，这可能是由于它们的酮烯胺形式具有较强的分子内 N-H----O 键。然而，通过添加一个影响电荷分布的硝基，可使生物效应和与 DNA 的结合发生微妙的变化。
• ——
  作者：T. M. Shironina、N. M. Igidov、E. N. Koz'minykh、L. O. Kon'shina、Yu. S. Kasatkina、V. O. Koz'minykh

  DOI：10.1023/a:1013431407273

  日期：——

  Reactions of 1,6-disubstituted 3,4-dihydroxy-2,4-hexadiene-1,6-diones with hydrazine hydrate or hydrochloride afforded heterocyclization products, 3,3'-bipyrazoles. The chemoselective reaction of 1,6-diaryl-3,4-dihydroxy-2,4-hexadiene-1,6-diones with arylhydrazines gave rise to 1,1',5,5'-tetraaryl-3,3'-bipyrazoles and 1,5-diaryl-3-aroylacetylpyrazoles. The specific structural features of the pyrazole derivatives obtained are discussed. Some pyrazoles show bacteriostatic and antileukemic activity.
• Chemistry of 2-methylene-2,3-dihydro-3-furanones
  作者：E. N. Kozminykh、N. M. Igidov、G. A. Shavkunova、V. O. Kozminykh

  DOI：10.1007/bf02495929

  日期：1997.7

  2-p-Chlorobenzoylmethylene-5-phenyl-2,3-dihydro-3-furanone reacts with arylamines or N-arylideneamines to form the products of ring opening, 1,6-diaryl-1-arylamino-4-hydroxy-1,4-hexadiene-3,6-diones. The reaction of 5-aryl-2-p-chlorobenzoylmethylene-2,3-dihydro-3-furanones with o-aminophenol afforded 3-p-chlorobenzoylmethylene-3,4-dihydro-2H-benzo[b]-1,4-oxazin-2-one. Nucleophilic attack of amines is directed either to electrophilic centers at the C(5) and C(2) atoms or to the carbonyl group of the 2-phenacylidene substituent of the 3-oxofuran ring.
• Synthesis and antimicrobial activity of 2-substituted 5-aryl-2,3-dihydro-3-furanones and 1,6-diaryl-3,4-dihydroxy-2,4-hexadien-1,6-diones
  作者：V. O. Koz'minykh、N. M. Igidov、E. N. Koz'minykh、L. O. Kon'shina、Z. N. Semenova、N. V. Lyadova、A. N. Plaksina、Yu. S. Andreichikov

  DOI：10.1007/bf00778981

  日期：1991.12
• 1,3,4,6-Tetracarbonyl Compounds. I. The Novel Synthesis of 1,6-Diaryl-3,4-dihydroxy-hexa-2,4-diene-1,6-diones from 5-Aryl-furan-2,3-diones
  作者：Vladislav O. Kozminykh、Larisa O. Konshina、Nazim M. Igidov

  DOI：10.1002/prac.19933350813

  日期：——