dimethyl((4-(trifluoromethyl)phenyl)imino)-λ⁶-sulfanone

• 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: dimethyl((4-(trifluoromethyl)phenyl)imino)-λ⁶-sulfanone
• 英文别名: Dimethyl((4-(trifluoromethyl)phenyl)imino)-L6-sulfanone；dimethyl-oxo-[4-(trifluoromethyl)phenyl]imino-λ6-sulfane
• 化学式: C₉H₁₀F₃NOS
• 分子量: 237.246
• InChiKey: ACQYNKOCIXEMKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  37.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  二甲基亚磺酰亚胺 、 4-碘三氟甲苯 在 氯化镍二甲氧基乙烷 、 [Ir(dF(CF₃)ppy)₂(dtbbpy)](PF₆) 、 三乙胺 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以51%的产率得到dimethyl((4-(trifluoromethyl)phenyl)imino)-λ⁶-sulfanone
  参考文献：
  名称：

  光氧化还原介导的亚磺酰亚胺与芳基碘化物的C N交叉偶联

  摘要：

  已经开发了新的光氧化还原催化的亚砜亚砜与芳基卤化物的C N偶联反应，用于亚砜亚砜的一般N-芳基化。反应在具有高化学选择性水平的可见光存在下进行，并且宽泛的功能性是可以容忍的。在药物发现中，对亚砜亚砜作为药效团的兴趣迅速增长，这种新方法在高官能团耐受性和化合物的后期官能化方面提供了潜力。

  DOI：

  10.1016/j.tetlet.2019.151100

文献信息

• Nickel‐Catalyzed <i>N</i> ‐Arylation of <i>NH</i> ‐Sulfoximines with Aryl Halides via Paired Electrolysis
  作者：Dong Liu、Zhao‐Ran Liu、Cong Ma、Ke‐Jin Jiao、Bing Sun、Lei Wei、Julien Lefranc、Simon Herbert、Tian‐Sheng Mei

  DOI：10.1002/anie.202016310

  日期：2021.4.19

  A novel strategy for the N‐arylation of NH‐sulfoximines has been developed by merging nickel catalysis and electrochemistry (in an undivided cell), thereby providing a practical method for the construction of sulfoximine derivatives. Paired electrolysis is employed in this protocol, so a sacrificial anode is not required. Owing to the mild reaction conditions, excellent functional group tolerance and

  通过合并镍催化和电化学反应（在未分池中），开发了一种新的NH-亚砜肟亚胺的N-芳基化策略，从而为构建亚磺酰亚胺衍生物提供了一种实用的方法。在该协议中采用了配对电解，因此不需要牺牲阳极。由于温和的反应条件，获得了优异的官能团耐受性和产率。初步的机理研究表明，在室温下，Ni II物种的阳极氧化对于促进从所得Ni III物种中还原性消除C-N键至关重要。
• Decarboxylative sulfoximination of benzoic acids enabled by photoinduced ligand-to-copper charge transfer
  作者：Peng Xu、Wanqi Su、Tobias Ritter

  DOI：10.1039/d2sc05442f

  日期：——

  solution to decarboxylative sulfoximination of benzoic acids; although thoroughly investigated, limited substrate scope and harsh reaction conditions still hold back traditional thermal aromatic decarboxylative functionalization. Herein, we realize the first decarboxylative sulfoximination of benzoic acids via photo-induced ligand to copper charge transfer (copper-LMCT)-enabled decarboxylative carbometalation

  亚砜亚胺是重要的合成支架，在药物发现中起着重要作用。苯甲酸脱羧亚磺酰亚胺化目前尚无解决方案；尽管进行了彻底的研究，但有限的底物范围和苛刻的反应条件仍然阻碍了传统的热芳烃脱羧功能化。在此，我们通过光诱导配体到铜电荷转移（铜-LMCT）实现了苯甲酸的首次脱羧亚磺酰亚胺化作用。该转化在温和的反应条件下进行，具有广泛的底物范围，可应用于复杂小分子的后期功能化。
• Thermal Nickel-Catalyzed <i>N</i>-Arylation of NH-Sulfoximines with (Hetero)aryl Chlorides Enabled by PhPAd-DalPhos Ligation
  作者：Samuel A. Fisher、Connor M. Simon、Peter L. Fox、Michael J. Cotnam、Patrick L. DeRoy、Mark Stradiotto

  DOI：10.1021/acs.orglett.3c04152

  日期：2024.2.23

  cross-coupling of NH-sulfoximines with (hetero)aryl chlorides, as well as bromide and sulfonate electrophiles, that makes use of the air-stable, commercial precatalyst (PhPAd-DalPhos)Ni(o-tol)Cl. Under optimized conditions a diverse electrophile scope is established, including the N-arylation of the pharmaceutical Clozapine. While 5 mol % Ni and 80 °C are commonly employed in this chemistry, successful examples

  我们报告了一种使用空气稳定的商用预催化剂 (PhPAd-DalPhos)Ni( o -tol) 使NH -亚砜亚胺与（杂）芳基氯以及溴化物和磺酸盐亲电试剂交叉偶联的通用方法克莱。在优化条件下，建立了多种亲电试剂范围，包括药物氯氮平的N-芳基化。虽然该化学反应通常采用 5 mol% Ni 和 80 °C，但本文也介绍了使用 1 mol% Ni 和/或 25 °C 的成功示例。竞争实验证实了在这些条件下NH-亚磺酰亚胺作为亲核试剂优于伯磺酰胺。
• 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.
• Photoredox mediated C N cross coupling of sulfoximines with aryl iodides
  作者：Sudhir Hande、Adelphe Mfuh、Scott Throner、Ye Wu、Qing Ye、XiaoLan Zheng

  DOI：10.1016/j.tetlet.2019.151100

  日期：2019.10

  A new photoredox-catalyzed CN coupling reaction of sulfoximines with aryl halides has been developed for a general N-arylation of sulfoximines. The reactions proceed in the presence of visible light with high levels of chemoselectivity and a wide range of functionality is tolerated. There is a rapidly increasing interest in sulfoximines as pharmacophores in drug discovery and this new method offers

  已经开发了新的光氧化还原催化的亚砜亚砜与芳基卤化物的C N偶联反应，用于亚砜亚砜的一般N-芳基化。反应在具有高化学选择性水平的可见光存在下进行，并且宽泛的功能性是可以容忍的。在药物发现中，对亚砜亚砜作为药效团的兴趣迅速增长，这种新方法在高官能团耐受性和化合物的后期官能化方面提供了潜力。