(1Z,5Z)-1,6-dihydroxy-1,6-diphenylhexa-1,5-diene-3,4-dione | 139266-61-8

• 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: (1Z,5Z)-1,6-dihydroxy-1,6-diphenylhexa-1,5-diene-3,4-dione
• 英文别名: (2Z,4Z)-1,6-diphenyl-3,4-dihydroxy-2,4-hexadiene-1,6-dione；1,6-diphenyl-3,4-dihydroxy-2,4-hexadiene-1,6-dione；3,4-dihydroxy-1,6-diphenyl-2,4-hexadiene-1,6 dione；3,4-dihydroxy-1,6-diphenyl-2,4-hexadiene-1,6-dione；3,4-dihydroxy-1,6-diphenylhexa-2,4-diene-1,6-dione；1,6-diphenyl-3,4-dihydroxyhexa-2,4-diene-1,6-dione
• CAS: 139266-61-8
• 化学式: C₁₈H₁₄O₄
• 分子量: 294.307
• InChiKey: YORIHZSVRUBUIT-WHYMJUELSA-N

物化性质

• 沸点：
  408.4±45.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  22.0
• 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：

  (1Z,5Z)-1,6-dihydroxy-1,6-diphenylhexa-1,5-diene-3,4-dione 在 一水合肼 作用下， 以 水 为溶剂， 以91%的产率得到5,5'-diphenyl-3,3'-bipyrazole
  参考文献：
  名称：

  摘要：

  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.

  DOI：

  10.1023/a:1013431407273
• 作为产物：
  描述：

  5-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95%的产率得到(1Z,5Z)-1,6-dihydroxy-1,6-diphenylhexa-1,5-diene-3,4-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。
• Solution, solid state structure and fluorescence studies of 2,3-functionalized quinoxalines: evidence for a π-delocalized keto-enamine form with N–H···O intramolecular hydrogen bonds
  作者：Rachid Touzani、Taibi Ben-Hadda、Sghir Elkadiri、Abdelkrim Ramdani、Olivier Maury、Hubert Le Bozec、Loic Toupet、Pierre H. Dixneuf

  DOI：10.1039/b009667i

  日期：——

  R = Ph; 2, R =  neo-Pen] with o-phenylenediamine or (R,R)-1,2-diaminocyclohexane. 1H, 13C and 15N NMR studies show that these derivatives are best described as their keto-enamine form with N–H···O intramolecular hydrogen bonds. This preferred tautomeric form is confirmed by X-ray structural studies of 3 and 5. Compounds 3 and 4, containing an extended delocalized π-system, exhibit fluorescence properties

  三喹喔啉衍生物3，4和5 是由tetraones RC（缩合来制备O）-CH 2 -C（O） - （O）-CH 2 -C（O）R [ 1，R = Ph值; 在图2中，R ＝  与邻-苯二胺或（R，R）-1,2-二氨基环己烷的新-Pen] 。1 H，13 C和15 N NMR研究表明，这些衍生物最好被描述为具有N–H··O分子内氢键的酮-烯胺形式。该优选的互变异构形式通过X-射线的X射线结构研究得到证实。3和5。包含扩展的离域π系统的化合物3 和4表现出荧光性质。相反，当中央芳族部分被环己基取代时，荧光在5中被抑制。
• Sphingosine kinase inhibitors
  申请人：The Pennsylvania State University Research Foundation

  公开号：US20040034075A1

  公开（公告）日：2004-02-19

  The invention relates to compounds, compositions and methods for inhibiting sphingosine kinase and for treating or preventing hyperproliferative disease, autoimmune disease, inflammatory disease, or allergy.

  本发明涉及用于抑制鞘氨醇激酶和治疗或预防过度增殖性疾病、自身免疫性疾病、炎症性疾病或过敏症的化合物、组合物和方法。
• 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.
• Koz'minykh; Igidov; Koz'minykh, Russian Journal of Organic Chemistry, 2000, vol. 36, # 9, p. 1341 - 1345
  作者：Koz'minykh、Igidov、Koz'minykh、Shavkunova、Sof'ina

  DOI：——

  日期：——