N-(4-fluoro)phenyl-S-phenyl-S-methylsulfoximine | 1140233-93-7

• 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-(4-fluoro)phenyl-S-phenyl-S-methylsulfoximine
• 英文别名: (4-Fluorophenyl)imino-methyl-oxo-phenyl-lambda6-sulfane；(4-fluorophenyl)imino-methyl-oxo-phenyl-λ6-sulfane
• CAS: 1140233-93-7
• 化学式: C₁₃H₁₂FNOS
• 分子量: 249.309
• InChiKey: FSYCTHZHAQITQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：
  3

反应信息

• 作为产物：
  描述：

  4-氟苯硼酸 、 (甲基亚砜亚胺基)苯 在 4-二甲氨基吡啶 、 copper(l) iodide 作用下， 以 甲醇 为溶剂， 反应 0.75h， 以86%的产率得到N-(4-fluoro)phenyl-S-phenyl-S-methylsulfoximine
  参考文献：
  名称：

  在温和条件下铜催化的亚砜基亚砜与亚砜基亚砜的亚甲基化

  摘要：

  抽象的 在室温下，使用碘化亚铜（I）和4-DMAP可将亚砜基与不同的芳基硼酸（包括位阻硼酸）进行N-芳基化反应。此外，首次证明了生物学上相关的1-甲硫氨酸亚磺酰亚胺的N-芳基化。所有这些反应在短时间内以优异的产率提供了所需的产物。优化的反应条件非常适合磺胺嘧啶与反式-2-苯基乙烯基硼酸进行N-乙烯基化的任务。 在室温下，使用碘化亚铜（I）和4-DMAP可将亚砜基与不同的芳基硼酸（包括位阻硼酸）进行N-芳基化反应。此外，首次证明了生物学上相关的1-甲硫氨酸亚磺酰亚胺的N-芳基化。所有这些反应在短时间内以优异的产率提供了所需的产物。优化的反应条件非常适合磺胺嘧啶与反式-2-苯基乙烯基硼酸进行N-乙烯基化的任务。

  DOI：

  10.1055/s-0037-1612216

文献信息

• 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。
• 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。
• Ligand-to-Copper Charge-Transfer-Enabled C–H Sulfoximination of Arenes
  作者：Wanqi Su、Peng Xu、Roland Petzold、Jiyao Yan、Tobias Ritter

  DOI：10.1021/acs.orglett.3c00256

  日期：2023.2.17

  photoinduced sulfoximine-to-copper charge-transfer-enabled generation of sulfoximinyl radicals directly from NH-sulfoximines for C–H sulfoximination of arenes via radical addition. Through copper-LMCT, N-arylation of NH-sulfoximines was achieved for the first time using arenes of different electronic structures as the aryl donors.

  在此，我们报道了一种光诱导的亚砜亚胺到铜电荷转移，能够直接从NH-亚砜亚胺生成亚砜亚胺自由基，用于通过自由基加成对芳烃进行 C-H 亚磺酰亚胺化。通过铜-LMCT，首次使用不同电子结构的芳烃作为芳基供体实现了NH-亚砜亚胺的N-芳基化。
• 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.
• Mild Copper–TBAF-Catalyzed <i>N</i>-Arylation of Sulfoximines with Aryl Siloxanes
  作者：Jaeeun Kim、Jinpyo Ok、Sanghyuck Kim、Wonseok Choi、Phil Ho Lee

  DOI：10.1021/ol502174n

  日期：2014.9.5

  An efficient copper-TBAF-catalyzed C-N bond formation of sulfoximines with arylsiloxanes in dichloromethane at room temperature, affording the desired N-aryl sulfoximines in good to excellent yields under an oxygen atmosphere, is reported. This method complements the existing synthetic approaches due to some advantageous properties of arylsiloxanes such as availability, low toxicity, ease of handling, high stability, and environmental benignity under mild reaction conditions, thus opening a new approach to practical C-N bond formation.