4-((4-bromobenzyl)thio)phthalonitrile | 1415344-01-2

• 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: 4-((4-bromobenzyl)thio)phthalonitrile
• 英文别名: 4-[(4-Bromobenzyl)Sulfanyl]Phthalonitrile；4-[(4-bromophenyl)methylsulfanyl]benzene-1,2-dicarbonitrile
• CAS: 1415344-01-2
• 化学式: C₁₅H₉BrN₂S
• 分子量: 329.22
• InChiKey: BYMBXVDUMFYTBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-硝基邻苯二甲腈 、 4-溴苄硫醇 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 4-((4-bromobenzyl)thio)phthalonitrile
  参考文献：
  名称：

  化学传感器酞菁对 Pd2+ 离子的选择性；合成、表征、量子化学计算、光化学和光物理特性

  摘要：

  摘要 在本研究中，根据文献，通过（4-溴苯基）甲硫醇与 4-硝基邻苯二甲腈的亲核置换反应制备配体（1）及其新型外围取代四酞菁 [CuPc (2)、ZnPc (3) 和 GaPc (4)] 准备。从化合物 (1) 获得的酞菁通过 FT-IR、1H NMR、UV-Vis 光谱数据、元素分析和 MALDI-TOF 进行表征。新型酞菁 [CuPc (2)、ZnPc (3) 和 GaPc (4)] 高度可溶于常见有机溶剂，如 CHCl3、THF、CH2Cl2、DMSO 和 DMF。Pd2+ 离子对荧光发射和 UV-Vis 光谱的影响是通过添加越来越多的 Pd2+ 离子来进行的。由于特殊的化学结构，这种功能性酞菁对 Pd2+ 离子表现出 H 型聚集，可用作 Pd2+ 离子的选择性化学传感器。此外，还研究了配体 (1) 和相关金属酞菁 [CuPc (2)、ZnPc (3) 和 GaPc (4)] 的分子

  DOI：

  10.1016/j.molstruc.2018.11.094

文献信息

• Selective chemosensor phthalocyanines for Pd2+ ions; synthesis, characterization, quantum chemical calculation, photochemical and photophysical properties
  作者：Armağan Günsel、Erkan Kırbaç、Burak Tüzün、Ali Erdoğmuş、Ahmet T. Bilgiçli、M. Nilüfer Yarasir

  DOI：10.1016/j.molstruc.2018.11.094

  日期：2019.3

  phthalocyanines [CuPc (2), ZnPc (3) and GaPc (4)] were highly soluble in common organic solvents such as CHCl3, THF, CH2Cl2, DMSO and DMF. The effect of Pd2+ ions on the fluorescence emission and UV–Vis spectra were performed with addition of increasing amounts of Pd2+ ions. This functional phthalocyanines exhibited H-type aggregation versus Pd2+ ions due to special chemical structures, which can be used as a

  摘要 在本研究中，根据文献，通过（4-溴苯基）甲硫醇与 4-硝基邻苯二甲腈的亲核置换反应制备配体（1）及其新型外围取代四酞菁 [CuPc (2)、ZnPc (3) 和 GaPc (4)] 准备。从化合物 (1) 获得的酞菁通过 FT-IR、1H NMR、UV-Vis 光谱数据、元素分析和 MALDI-TOF 进行表征。新型酞菁 [CuPc (2)、ZnPc (3) 和 GaPc (4)] 高度可溶于常见有机溶剂，如 CHCl3、THF、CH2Cl2、DMSO 和 DMF。Pd2+ 离子对荧光发射和 UV-Vis 光谱的影响是通过添加越来越多的 Pd2+ 离子来进行的。由于特殊的化学结构，这种功能性酞菁对 Pd2+ 离子表现出 H 型聚集，可用作 Pd2+ 离子的选择性化学传感器。此外，还研究了配体 (1) 和相关金属酞菁 [CuPc (2)、ZnPc (3) 和 GaPc (4)] 的分子
• Sulfanylphthalonitrile analogues as selective and potent inhibitors of monoamine oxidase B
  作者：Mietha M. Van der Walt、Gisella Terre’Blanche、Anna C.U. Lourens、Anél Petzer、Jacobus P. Petzer

  DOI：10.1016/j.bmcl.2012.10.070

  日期：2012.12

  It has recently been reported that nitrile containing compounds frequently act as potent monoamine oxidase B (MAO-B) inhibitors. Modelling studies suggest that this high potency inhibition may rely, at least in part, on polar interactions between nitrile functional groups and polar moieties within the MAO-B substrate cavity. In an attempt to identify potent and selective inhibitors of MAO-B and to contribute to the known structure-activity relationships of MAO inhibition by nitrile containing compounds, the present study examined the MAO inhibitory properties of series of novel sulfanylphthalonitriles and sulfanylbenzonitriles. The results document that the evaluated compounds are potent and selective MAO-B inhibitors with most homologues possessing IC50 values in the nanomolar range. In general, the sulfanylphthalonitriles exhibited higher binding affinities for MAO-B than the corresponding sulfanylbenzonitrile homologues. Among the compounds evaluated, 4-[(4-bromobenzyl)sulfanyl]phthalonitrile is a particularly promising inhibitor since it displayed a high degree of selectivity (8720-fold) for MAO-B over MAO-A, and potent MAO-B inhibition (IC50 = 0.025 mu M). Based on these observations, this structure may serve as a lead for the development of therapies for neurodegenerative disorders such as Parkinson's disease. (C) 2012 Elsevier Ltd. All rights reserved.
• C-S coupling with nitro group as leaving group via simple inorganic salt catalysis
  作者：Maojie Xuan、Chunlei Lu、Bo-Lin Lin

  DOI：10.1016/j.cclet.2019.07.012

  日期：2020.1

  An efficient and practical synthetic protocol to synthesize nonsymmetrical aryl thioethers by nucleophilic aromatic substitution (SNAr) reaction of nitroarenes by thiols with potassium phosphate as the catalyst is described. Various moderate to strong electron-withdrawing functional groups are tolerated by the system to provide thioethers in a good to excellent yields. We also showed that the present method allows access to 3 drug examples in a short reaction time. Finally, mechanistic studies suggest that the reaction may form the classic Meisenheimer complex through a two-step addition elimination mechanism. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.