2-(2-bromophenylsulfanyl)propionitrile | 819071-81-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(2-bromophenylsulfanyl)propionitrile
• 英文别名: 2-((2-bromophenyl)thio)propanenitrile；2-(2-Bromophenyl)sulfanylpropanenitrile
• CAS: 819071-81-3
• 化学式: C₉H₈BrNS
• mdl: MFCD13417129
• 分子量: 242.139
• InChiKey: FXNSLUAKEYCSGE-UHFFFAOYSA-N

物化性质

• 沸点：
  311.7±27.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-bromophenylsulfanyl)propionitrile 在 四(三苯基膦)钯 、 sodium methylate 、 sodium carbonate 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 反应 110.0h， 生成 2-[1-(Biphenyl-2-ylsulfanyl)-ethyl]-4,5-dihydro-1H-imidazole
  参考文献：
  名称：

  α₂-Adrenoreceptors Profile Modulation. 2. Biphenyline Analogues as Tools for Selective Activation of the α_2C-Subtype

  摘要：

  A series of derivatives structurally related to biphenyline (3) was designed with the aim to modulate selectivity toward the alpha(2)-AR subtypes. The results obtained demonstrated that the presence of a correctly oriented function with positive electronic effect (+sigma) in portion X of the ligands is an important factor for significant alpha(2C)-subtype selectivity (imidazolines 5, 13, 16, and 19). Homology modeling and docking studies support experimental data and highlight the crucial role for the hydrogen bond between the pyridine nitrogen in. position 3 of 5 and the NH-indole ring of Trp6.48, which is favorably oriented in the alpha(2C)-subtype, only.

  DOI：

  10.1021/jm0408215
• 作为产物：
  描述：

  2-氯丙腈 、 2-溴硫代苯酚 在 potassium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 8.0h， 以58%的产率得到2-(2-bromophenylsulfanyl)propionitrile
  参考文献：
  名称：

  α₂-Adrenoreceptors Profile Modulation. 2. Biphenyline Analogues as Tools for Selective Activation of the α_2C-Subtype

  摘要：

  A series of derivatives structurally related to biphenyline (3) was designed with the aim to modulate selectivity toward the alpha(2)-AR subtypes. The results obtained demonstrated that the presence of a correctly oriented function with positive electronic effect (+sigma) in portion X of the ligands is an important factor for significant alpha(2C)-subtype selectivity (imidazolines 5, 13, 16, and 19). Homology modeling and docking studies support experimental data and highlight the crucial role for the hydrogen bond between the pyridine nitrogen in. position 3 of 5 and the NH-indole ring of Trp6.48, which is favorably oriented in the alpha(2C)-subtype, only.

  DOI：

  10.1021/jm0408215

文献信息

• Enantioselective Synthesis of α‐Thiocarboxylic Acids by Nitrilase Biocatalysed Dynamic Kinetic Resolution of α‐Thionitriles
  作者：Kate Lauder、Silvia Anselmi、James D. Finnigan、Yuyin Qi、Simon J. Charnock、Daniele Castagnolo

  DOI：10.1002/chem.202001108

  日期：2020.8.17

  The enantioselective synthesis of α‐thiocarboxylic acids by biocatalytic dynamic kinetic resolution (DKR) of nitrile precursors exploiting nitrilase enzymes is described. A panel of 35 nitrilase biocatalysts were screened and enzymes Nit27 and Nit34 were found to catalyse the DKR of racemic α‐thionitriles under mild conditions, affording the corresponding carboxylic acids with high conversions and

  描述了利用腈水解酶通过腈前体的生物催化动态动力学拆分 (DKR) 对映选择性合成 α-硫代羧酸。筛选了一组 35 种腈水解酶生物催化剂，发现酶 Nit27 和 Nit34 在温和条件下催化外消旋 α-硫腈的 DKR，提供具有高转化率和良好至优异ee的相应羧酸。生物催化转化过程中原位产生的氨有利于腈对映体的外消旋化，进而有利于 DKR 的外消旋化，无需任何外部添加剂碱。