2,5-bis-(4-cyanophenyl)-1,4-dimethoxybenzene | 206867-52-9

• 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: 2,5-bis-(4-cyanophenyl)-1,4-dimethoxybenzene
• 英文别名: 2',5'-Dimethoxy-[1,1':4',1''-terphenyl]-4,4''-dicarbonitrile；4-[4-(4-cyanophenyl)-2,5-dimethoxyphenyl]benzonitrile
• CAS: 206867-52-9
• 化学式: C₂₂H₁₆N₂O₂
• 分子量: 340.381
• InChiKey: BCQNLSGWSDQLFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  66
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  2,5-bis-(4-cyanophenyl)-1,4-dimethoxybenzene 在 (trimethylsilyl)aminolithium 、 盐酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 以90%的产率得到
  参考文献：
  名称：

  Synthesis, DNA Affinity, and Antiprotozoal Activity of Linear Dications:  Terphenyl Diamidines and Analogues

  摘要：

  Diamidines 10a-g and 18a, b were obtained from dinitriles 9a-g and 15a, b by treatment with lithium trimethylsilylamide or upon hydrogenation of bis-O-acetoxyamidoximes. Dinitriles 9a-g were prepared via Suzuki reactions between arylboronic acids and arylnitriles. Potential prodrugs 12a-f and 17 were prepared via methylation of the diamidoximes 11a-f and 16a. Significant DNA affinities for rigid-rod molecules were observed. Compounds 10a, 10b, 10d, 18a, and 18b show IC50 values of 5 nM or less against Trypanosoma brucei rhodesiense ( T. b. r.) and 10a, 10b, 10e, 18a, and 18b gave similar ones against Plasmodium falciparum ( P. f.). The dications, 10a, 10d, 10f, and 10g are more active than furamidine in vivo. The prodrugs are only moderately effective on oral administration. Mouse liver microsome bioconversion of the methamidoxime prodrugs is significantly reduced from that of pafuramidine and suggests that the in vivo efficacy of these prodrugs is, in part, due to poor bioconversion.

  DOI：

  10.1021/jm060470p
• 作为产物：
  描述：

  对苯二甲醚 在 四(三苯基膦)钯 、 萘 、 溴 、 lithium 、 zinc(II) chloride 作用下， 以 溶剂黄146 为溶剂， 反应 29.0h， 生成 2,5-bis-(4-cyanophenyl)-1,4-dimethoxybenzene
  参考文献：
  名称：

  Efficient Synthesis of Symmetrical 2,5-Disubstituted Benzoquinones via Palladium-Catalyzed Double Negishi Coupling

  摘要：

  DOI：

  10.1021/jo9721812

文献信息

• On/off electrochemical switches based on quinone-bisketals
  作者：Noelia Fuentes、Luis Álvarez de Cienfuegos、Andrés Parra、Duane Choquesillo-Lazarte、Juan M. García-Ruiz、M. Luisa Marcos、Elena Buñuel、Maria Ribagorda、M. Carmen Carreño、Diego J. Cárdenas、Juan M. Cuerva

  DOI：10.1039/c0cc04388e

  日期：——

  The synthesis and anodic oxidation of a variety of 2,5-diaryl or dialkynylaryl substituted 1,4-dialkoxybenzenes to quinone bisketals is described. The study of the X-ray structures and electrochemical and spectroscopic properties evidenced that these pairs constitute a first approach to the concept of a molecular nanofuse.

  描述了多种2,5-二芳基或二炔基芳基取代的1,4-二烷氧基苯合成及其阳极氧化为醌双酮的过程。X射线结构、 electrochemical和光谱特性的研究表明，这些配体构成了分子纳米保险丝概念的首次尝试。
• Synthesis, DNA Affinity, and Antiprotozoal Activity of Linear Dications:  Terphenyl Diamidines and Analogues
  作者：Mohamed A. Ismail、Reem K. Arafa、Reto Brun、Tanja Wenzler、Yi Miao、W. David Wilson、Claudia Generaux、Arlene Bridges、James E. Hall、David W. Boykin

  DOI：10.1021/jm060470p

  日期：2006.8.1

  Diamidines 10a-g and 18a, b were obtained from dinitriles 9a-g and 15a, b by treatment with lithium trimethylsilylamide or upon hydrogenation of bis-O-acetoxyamidoximes. Dinitriles 9a-g were prepared via Suzuki reactions between arylboronic acids and arylnitriles. Potential prodrugs 12a-f and 17 were prepared via methylation of the diamidoximes 11a-f and 16a. Significant DNA affinities for rigid-rod molecules were observed. Compounds 10a, 10b, 10d, 18a, and 18b show IC50 values of 5 nM or less against Trypanosoma brucei rhodesiense ( T. b. r.) and 10a, 10b, 10e, 18a, and 18b gave similar ones against Plasmodium falciparum ( P. f.). The dications, 10a, 10d, 10f, and 10g are more active than furamidine in vivo. The prodrugs are only moderately effective on oral administration. Mouse liver microsome bioconversion of the methamidoxime prodrugs is significantly reduced from that of pafuramidine and suggests that the in vivo efficacy of these prodrugs is, in part, due to poor bioconversion.
• Efficient Synthesis of Symmetrical 2,5-Disubstituted Benzoquinones via Palladium-Catalyzed Double Negishi Coupling
  作者：Andreas Palmgren、Atli Thorarensen、Jan-E. Bäckvall

  DOI：10.1021/jo9721812

  日期：1998.5.1