4-(benzylthio)phthalonitrile | 496783-57-4

• 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-(benzylthio)phthalonitrile
• 英文别名: 4-(Benzylsulfanyl)Phthalonitrile；4-benzylsulfanylbenzene-1,2-dicarbonitrile
• CAS: 496783-57-4
• 化学式: C₁₅H₁₀N₂S
• 分子量: 250.324
• InChiKey: DZQBBCRLXMGVGW-UHFFFAOYSA-N

物化性质

• 沸点：
  453.8±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 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

• 作为反应物：
  描述：

  4-(benzylthio)phthalonitrile 在 aluminum (III) chloride 作用下， 以 苯 为溶剂， 以42 %的产率得到4-mercapto-1,2-dicyanobenzene
  参考文献：
  名称：

  硫族取代锌(II)酞菁的光物理学案例研究

  摘要：

  描述了硫属原子对 30 种定制的含硫属元素的四取代锌 (II) 酞菁的光物理性质（吸收和荧光光谱、激发态寿命和单线态双氧光生）的影响的全面系统分析。系统间交叉率常数通过几种独立的方法进行估计，并显示出依赖性缩放为Z 0.4和ze 0.2 。

  DOI：

  10.1002/chem.202304083
• 作为产物：
  描述：

  4-硝基邻苯二甲腈 、 苄硫醇 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.25h， 以92%的产率得到4-(benzylthio)phthalonitrile
  参考文献：
  名称：

  在α和β位置被芳硫基四取代的酞菁氰基氧钛（IV）配合物的合成，电化学和光物理性质

  摘要：

  以下四取代基的合成，电化学和光物理性质 硫醇 氧钛 酞菁类首次报道：1，（4）-（四苯基硫代邻苯二甲酸氰基钛）氧化钛（IV）（5a）；1，（4）-（四苄硫基酞菁钛）氧化钛（IV）（5b）; 2 ,,（3）-（四苯基硫代酞菁钛）四氧化钛（6a）和2，（3）-（苄基硫代酞菁锡）四氧化钛（6b）。所有四个复合物的循环伏安图均相似，其中三个可逆减少每一对都涉及一个电子转移过程。通过光谱电化学证实前两次还原是基于金属的还原，这是由于Ti IV Pc -2 / Ti III Pc -2和Ti III Pc -2 / Ti II Pc -2的氧化还原过程，而最后一次还原被确认是Ti II Pc -2 / Ti II Pc -3导致的基于环的还原。观察到较低的荧光量子产率（0.05–0.14），相对较长的三重态寿命（150–210 µs）和三重态产率（0.31至0.82）。

  DOI：

  10.1039/b607538j

文献信息

• Synthesis and electrochemical properties of benzyl-mercapto and dodecyl-mercapto tetrasubstituted manganese phthalocyanine complexes
  作者：Bolade Agboola、Kenneth I. Ozoemena、Philippe Westbroek、Tebello Nyokong

  DOI：10.1016/j.electacta.2006.09.002

  日期：2007.2

  Manganese tetrakis (benzyl-mercapto) phthalocyanine (MnTBMPc) and manganese tetrakis (dodecyl-mercapto) phthalocyanine (MnTDMPc) complexes were synthesized and their spectral and electrochemical properties are reported. Cyclic voltammetric data showed three reversible to quasi-reversible and two irreversible redox processes for both complexes. Ring substituents influenced the positions of both oxidation

  合成了锰四（苄基巯基）酞菁（MnTBMPc）和锰四（十二烷基巯基）酞菁（MnTDMPc）配合物，并报道了它们的光谱和电化学性质。循环伏安数据显示两种配合物的三个可逆至准可逆和两个不可逆氧化还原过程。环取代基影响氧化和还原氧化还原对的位置。光谱电化学证实前两个减少是由于Mn III Pc 2- / Mn II Pc 2-和Mn II Pc 3- / Mn II Pc 2-流程。提出了使用硫醇取代的MnPc配合物形成自组装单分子层（SAMs）的第一个例子，发现该SAMs具有对某些法拉第反应的阻断特性。
• 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.
• Synthesis and electrochemical characterisation of benzylmercapto and dodecylmercapto tetra substituted cobalt, iron, and zinc phthalocyanines complexes
  作者：Bolade Agboola、Kenneth I. Ozoemena、Tebello Nyokong

  DOI：10.1016/j.electacta.2005.12.017

  日期：2006.6

  The work reports on cyclic voltammetry (CV), square wave voltammetry and spectroelectrochemistry of the following complexes: tetrakis (benzylmercapto) phthalocyanine complexes of Zn(II) (ZnTBMPc, 4a), Co(II) (CoTBMPc, 5a), and Fe(II) (FeTBMPc 6a); tetrakis (dodecylmercapto) phthalocyanine complexes of Zn(II) (ZnTDMPc, 4b), Co(II) (CoTDMPc, 5b), and Fe(II) (FeTDMPc, 6b). More reversible CV couples were observed for complexes 4a, 5a, and 6a containing thiol phenyl ring substituents. Complexes 4b, 5b, and 6b containing long chain thiol substituents showed less reversible couples. Complexes 6a and 6b showed a relatively large number of redox processes (5 for 6a and 6 for 6b) within the potential window employed in this work. The processes for FePc derivatives (6a) are assigned to (FePc-1)-Pc-II/(FePc-2)-Pc-III, (FePc-2)-Pc-III/(FePc-2)-Pc-II, (FePc-2)-Pc-II/(FePc-2)-Pc-I, (FePc-2)-Pc-I/(FePc-3)-Pc-I, and (FePc-3)-Pc-I/(FePc-4)-Pc-I and for the CoPc derivative (5a) to (CoPc-1)-Pc-III/(CoPc-2)-Pc-III, (CoPc-2)-Pc-III/(CoPc-2)-Pc-II, (CoPc-2)-Pc-II/(CoPc-2)-Pc-I, and (CoPc-2)-Pc-I/(CoPc-3)-Pc-I. (c) 2005 Elsevier Ltd. All rights reserved.
• Electrochemical properties of benzylmercapto and dodecylmercapto tetra substituted nickel phthalocyanine complexes: Electrocatalytic oxidation of nitrite
  作者：Bolade O. Agboola、Kenneth I. Ozoemena、Tebello Nyokong

  DOI：10.1016/j.electacta.2006.04.033

  日期：2006.9

  Nickel tetrakis(benzylmercapto)phthalocyanine (NiTBMPc) and nickel tetrakis(dodecylmercapto)phthalocyanine (NiTDMPc) complexes were synthesized and their spectral and electrochemical properties reported. The CV showed four or five redox processes for NiTBMPc and NiTDMPc, respectively. For the first time, spectroelectrochemistry gave evidence for the formation of Ni-II/Ni-I process in a NiPc complex. The rest of the processes were ring based. The NiTBMPc complex was successfully deposited on both gold and glassy carbon electrodes by electropolymerisation while NiTDMPc complex was deposited on gold electrode only. The films were electro-transformed in aqueous 0.1 M NaOH solution to the O-Ni-O oxo bridged form. The modified electrodes were characterized using electrochemical impedance spectroscopy and the results showed typical behavior for modified electrodes. Electrodes with poly-Ni(OH)Pcs films exhibited higher charge transfer resistance values, RP than their corresponding poly-NiPcs films counterparts. All the modified electrodes showed improved catalytic activities than the unmodified electrodes towards nitrite ions electrooxidation. Better catalytic activities were observed for the modified electrodes when they were transformed to O-Ni-O oxo bridge form. All the modified electrodes exhibited high resistance to electrode surface passivation. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis, characterization and application of monocarboxy-phthalocyanine-single walled carbon nanotube conjugates in electrocatalysis
  作者：Tawanda Mugadza、Tebello Nyokong

  DOI：10.1016/j.poly.2011.04.020

  日期：2011.6

  In this paper we report on the synthesis, characterization and use of monocarboxy-phthalocyanine-single walled carbon nanotube conjugates in the electrocatalysis of amitrole and diuron. UV-Vis, FTIR and XRD spectroscopies were used in the characterization of cobalt(II)-tris(benzyl-mercapto)-mono(carboxyphenoxy)-phthalocyanine conjugates (CoMCPc-PA-SWCNT(linked)), while AFM was used to show changes in surface morphologies of the modified electrodes. Cyclic voltammetry and chronoamperometry were used for the electrocatalytic oxidation of amitrole and diuron on the modified glassy carbon electrode. The catalytic rate constants for amitrole and diuron were found to be 1.83 x 10(6) and 1.99 x 106 M(-1) s(-1), respectively. The linear range for both was 1.0 x 10(-5)-2.0 x 10(-4) M, with sensitivities of 5.10 and 3.70 A mol(-1) L cm(-2) for amitrole and diuron, respectively. The limits of detection were estimated to be 0.14 and 0.20 mu M for amitrole and diuron, respectively, using the 38 notation. (C) 2011 Elsevier Ltd. All rights reserved.