rac-N-[(2-chloro)-phenyl]-S-phenyl-S-methylsulfoximine

• 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: rac-N-[(2-chloro)-phenyl]-S-phenyl-S-methylsulfoximine
• 英文别名: N-(2-chlorophenyl)-S-methyl-S-phenylsulfoximine；N-[(2-chloro)-phenyl]-S-phenyl-S-methylsulfoximine；(2-Chlorophenyl)imino-methyl-oxo-phenyl-lambda6-sulfane；(2-chlorophenyl)imino-methyl-oxo-phenyl-λ6-sulfane
• 化学式: C₁₃H₁₂ClNOS
• 分子量: 265.763
• InChiKey: GCMFTHZYZAMGGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  37.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-氯-2-碘苯 、 (甲基亚砜亚胺基)苯 在 iron(III) chloride 、 K₃PO₄ 、 N,N-二甲基乙二胺 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以74%的产率得到rac-N-[(2-chloro)-phenyl]-S-phenyl-S-methylsulfoximine
  参考文献：
  名称：

  铁催化的磺胺嘧啶与芳基碘化物的CN交叉偶联

  摘要：

  据报道，一种廉价且实验上简单的，铁催化的NH-亚磺酰亚胺与芳基碘化物的N-芳基化反应。这种与已知的钯和铜催化方法互补的方法，其特征在于使用环保的FeCl 3和N，N'-二甲基乙二胺（DMEDA）的组合作为催化体系，并可以高产率高效地制备各种N-芳基亚砜基。

  DOI：

  10.1002/adsc.200700508

文献信息

• Cu(OAc)₂-Catalyzed N-Arylations of Sulfoximines with Aryl Boronic Acids
  作者：Christian Moessner、Carsten Bolm

  DOI：10.1021/ol050816a

  日期：2005.6.1

  [reaction: see text] A simple and mild copper salt-catalyzed N-arylation of sulfoximines in high yields is reported. Cu(OAc)(2) activates aryl boronic acids for the reaction with NH-sulfoximines without additional base or heating. Furthermore, this new method allows the preparation of N-arylated sulfoximines, which have previously been more difficult to access.

  [反应：见正文]据报道，简单，温和的铜盐催化的亚砜亚胺的N-芳基化反应具有很高的收率。Cu（OAc）（2）可以活化芳基硼酸，使其与NH-亚磺酰亚胺反应，而无需额外的碱或加热。此外，这种新方法可以制备以前难以获得的N-芳基亚砜亚砜。
• Copper-catalyzed denitrogenative N-arylation of sulfoximines and sulfonamides with arylhydrazines
  作者：Wanrong Dong、Chaoyang Liu、Xinchi Ma、Yingjun Zhang、Zhihong Peng、Dexun Xie、Delie An

  DOI：10.1016/j.tet.2019.05.039

  日期：2019.7

  A Cu-mediated ligand-free arylation of NH-sulfoximines and sulfonamides by arylhydrazine hydrochlorides was herein demonstrated. The oxidative transformation provided an easy access towards N-aryl sulfoximines and sulfonamides in high yields (up to 93% yields) with broad functional groups tolerance (up to 36 examples). The protocol was proposed to take place through the free radical pathway based on

  本文证明了芳基肼盐酸盐的Cu介导的NH-亚砜亚胺和磺酰胺的无配体芳基化。氧化转化提供了高收率（最高93％的收率）和宽泛的官能团耐受性（最多36个实例），可轻松获得N-芳基亚磺酰亚胺和磺酰胺。根据控制反应和EPR分析的结果，提出了通过自由基途径进行实验的方案。
• Transition-Metal-Free N-(o-Halo)arylation of Sulfoximines/Sulfonimidamides
  作者：Ganesh Chandra Nandi、V. R. Padma Priya、C. P. Irfana Jesin

  DOI：10.1055/a-1921-0875

  日期：2023.4

  A transition-metal-free novel route to access N-(o-halo)arylsulfoximines/sulfonimidamides is achieved by the reaction of sulfoximine/sulfonimidamide, aryne precursor, and CCl4/CBr4 in the presence of KF/18-crown-6. The in situ generated benzyne intermediate (from silyl aryl triflate) reacts with the nucleophile (sulfoximine/sulfonimidamide) and halide source (CCl4/CBr4) to yield the product in moderate

  在 KF/18-crown-6 存在下，通过亚砜亚胺/亚磺酰亚胺、芳烃前体和 CCl 4 /CBr 4的反应，实现了一种获得N -( o -halo) 芳基亚砜亚胺/亚磺酰亚胺的无过渡金属新途径. 原位产生的苯中间体（来自三氟甲磺酸甲硅烷基芳基酯）与亲核试剂（亚砜亚胺/磺酰亚胺）和卤化物源（CCl 4 /CBr 4）反应，以中等至良好的产率产生产物。该协议展示了广泛的底物范围。由不对称芳烃前体形成的区域异构体通过柱色谱有效分离。
• Sulfoximines from a Medicinal Chemist's Perspective: Physicochemical and in vitro Parameters Relevant for Drug Discovery
  作者：Marcus Frings、Carsten Bolm、Andreas Blum、Christian Gnamm

  DOI：10.1016/j.ejmech.2016.09.091

  日期：2017.1

  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.
• Iron-Catalyzed CN Cross-Coupling of Sulfoximines with Aryl Iodides
  作者：Arkaitz Correa、Carsten Bolm

  DOI：10.1002/adsc.200700508

  日期：2008.2.22

  An inexpensive and experimentally simple, iron-catalyzed N-arylation reaction of NH-sulfoximines with aryl iodides is reported. This complementary method to the known palladium- and copper-catalyzed ones features the use of a combination of environmentally friendly FeCl3 and N,N′-dimethylethylenediamine (DMEDA) as catalytic system and allows the efficient preparation of various N-arylsulfoximines in

  据报道，一种廉价且实验上简单的，铁催化的NH-亚磺酰亚胺与芳基碘化物的N-芳基化反应。这种与已知的钯和铜催化方法互补的方法，其特征在于使用环保的FeCl 3和N，N'-二甲基乙二胺（DMEDA）的组合作为催化体系，并可以高产率高效地制备各种N-芳基亚砜基。