4-((4-bromobenzyl)thio)benzonitrile | 1320161-18-9

• 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: 4-((4-bromobenzyl)thio)benzonitrile
• 英文别名: 4-[(4-Bromobenzyl)Sulfanyl]Benzonitrile；4-[(4-bromophenyl)methylsulfanyl]benzonitrile
• CAS: 1320161-18-9
• 化学式: C₁₄H₁₀BrNS
• 分子量: 304.21
• InChiKey: VGSIRAQVBHNNJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 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：
  49.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-溴苄硫醇 、 对硝基苯甲腈 在 potassium phosphate 、 18-冠醚-6 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以44%的产率得到4-((4-bromobenzyl)thio)benzonitrile
  参考文献：
  名称：

  C-S coupling with nitro group as leaving group via simple inorganic salt catalysis

  摘要：

  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.

  DOI：

  10.1016/j.cclet.2019.07.012

文献信息

• ADDP facilitates C–S bond formation from sulfonyl chlorides with alcohols
  作者：Gang Sun、Xin Liu、Jing Li、Jian-Xin Yang、Jun-Kai Xie、Xiaoan Wen、Hongbin Sun、Qing-Long Xu

  DOI：10.1039/d2nj06287a

  日期：——

  The formation of C–S bonds using cheap, stable and odorless sulfonyl chlorides and widely sourced and less toxic alcohols with the assistance of ADDP is reported. This method is suitable for a broad substrate scope and tolerates a broad range of functional groups. Additionally, our protocol provides a green and convenient methylating method utilizing methanol or methanol-d4 and allows trideuteromethylthiolation

  据报道，在 ADDP 的帮助下，使用廉价、稳定且无味的磺酰氯和来源广泛且毒性较低的醇形成 C-S 键。这种方法适用于广泛的底物范围，并且可以容忍范围广泛的官能团。此外，我们的方案提供了一种使用甲醇或甲醇-d 4的绿色便捷甲基化方法，并允许使用磺酰氯进行三氘甲基硫醇化。该方法可应用于天然产物和药物类似物的后期多样化。
• 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.
• Organophosphorus-Catalyzed “Dual-Substrate Deoxygenation” Strategy for C–S Bond Formation from Sulfonyl Chlorides and Alcohols/Acids
  作者：Gang Sun、Jing Li、Xin Liu、Yiting Liu、Xiaoan Wen、Hongbin Sun、Qing-Long Xu

  DOI：10.1021/acs.joc.3c00532

  日期：2023.7.7
• 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.