4-(phenethylthio)benzonitrile | 1415344-09-0

• 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-(phenethylthio)benzonitrile
• 英文别名: 4-[(2-Phenylethyl)Sulfanyl]Benzonitrile；4-(2-phenylethylsulfanyl)benzonitrile
• CAS: 1415344-09-0
• 化学式: C₁₅H₁₃NS
• 分子量: 239.341
• InChiKey: RGMRPDCULUSBNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  2-苯乙硫醇 、 对硝基苯甲腈 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 50.25h， 以25%的产率得到4-(phenethylthio)benzonitrile
  参考文献：
  名称：

  Sulfanylphthalonitrile analogues as selective and potent inhibitors of monoamine oxidase B

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2012.10.070

文献信息

• Thioetherification via Photoredox/Nickel Dual Catalysis
  作者：Matthieu Jouffroy、Christopher B. Kelly、Gary A. Molander

  DOI：10.1021/acs.orglett.6b00208

  日期：2016.2.19

  Hypervalent alkylsilicates represent new and readily accessible precursors for the generation of alkyl radicals under photoredox conditions. Alkyl radicals generated from such silicates serve as effective hydrogen atom abstractors from thiols, furnishing thiyl radicals. The reactive sulfur species generated in this manner can be funneled into a nickel-mediated cross-coupling cycle employing aromatic

  高价烷基硅酸盐代表了在光氧化还原条件下产生烷基自由基的新的和易于获得的前体。由这种硅酸盐产生的烷基自由基可作为有效的氢原子从硫醇中提取出氢原子，从而提供了噻吩基。可以将以这种方式产生的反应性硫物质漏入镍介导的交叉偶联循环中，该循环使用芳族溴化物提供硫醚。描述了该反应的偶然发现及其用于将各种芳族硫醇与各种芳基和杂芳基溴化物进行硫醚化的过程。S–H选择性H原子抽象事件使宽泛的官能团（包括带有质子部分的官能团）能够被耐受。