N-(p-Cyanophenyl)dimethylsulfoximid | 56158-12-4

• 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: N-(p-Cyanophenyl)dimethylsulfoximid
• 英文别名: N-(4-cyanophenyl)-dimethyl-sulfoximide；4-{[Dimethyl(oxo)-lambda~6~-sulfanylidene]amino}benzonitrile；4-[[dimethyl(oxo)-λ6-sulfanylidene]amino]benzonitrile
• CAS: 56158-12-4
• 化学式: C₉H₁₀N₂OS
• 分子量: 194.257
• InChiKey: FYTRDWNKMKCQSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二甲基亚磺酰亚胺 、 4-氰基苯硼酸 在 copper diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 N-(p-Cyanophenyl)dimethylsulfoximid
  参考文献：
  名称：

  Sulfoximines from a Medicinal Chemist's Perspective: Physicochemical and in vitro Parameters Relevant for Drug Discovery

  摘要：

  Sulfoximines, sulfondiimides and sulfonimidamides are fascinating but not yet fully explored variants of the common sulfone or sulfonamide motif. In this study, we report the physicochemical and in vitro properties of sulfoximines and compare them with related analogs and isosteres. Furthermore, we present a matched molecular pair analysis of compounds from drug discovery projects within Boehringer Ingelheim. We demonstrate that the sulfoximine moiety is a chemically stable, comparatively polar and weakly basic functional group, often leading to favorable aqueous solubility, permeability and metabolic stability. Moreover, their additional vectors at nitrogen enable simple chemical modifications and thus facilitate exploration and fine-tuning of the molecular properties. We conclude that sulfoximines and their congeners do not exhibit any intrinsic flaw but significantly enrich the toolbox of medicinal chemists. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.09.091

文献信息

• Redox-Neutral Cross-Coupling Amination with Weak <i>N-</i>Nucleophiles: Arylation of Anilines, Sulfonamides, Sulfoximines, Carbamates, and Imines via Nickelaelectrocatalysis
  作者：Chen Zhu、Ajit Prabhakar Kale、Huifeng Yue、Magnus Rueping

  DOI：10.1021/jacsau.1c00148

  日期：2021.7.26

  A nickel-catalyzed cross-coupling amination with weak nitrogen nucleophiles is described. Aryl halides as well as aryl tosylates can be efficiently coupled with a series of weak N-nucleophiles, including anilines, sulfonamides, sulfoximines, carbamates, and imines via concerted paired electrolysis. Notably, electron-deficient anilines and sulfonamides are also suitable substrates. Interestingly, when

  描述了镍催化交叉偶联胺化与弱氮亲核试剂。芳基卤化物和芳基甲苯磺酸酯可以通过协同配对电解与一系列弱N-亲核试剂有效偶联，包括苯胺、磺酰胺、亚砜亚胺、氨基甲酸酯和亚胺。值得注意的是，缺电子苯胺和磺酰胺也是合适的底物。有趣的是，当二苯甲酮亚胺用于芳基化时，可以通过碱基开关来解决形成胺和亚胺产物的产物选择性。此外，交流模式也可以成功应用。DFT 计算支持简化的还原消除途径。

表征谱图