N-(2-fluorobenzoyl)-S-methyl-S-phenylsulfoximine | 1426922-68-0

• 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-(2-fluorobenzoyl)-S-methyl-S-phenylsulfoximine
• 英文别名: 2-fluoro-N-(methyl(oxo)(phenyl)-λ6-sulfanylidene)benzamide；N-[2-fluorobenzoyl]-S-methyl-S-phenylsulfoximine
• CAS: 1426922-68-0
• 化学式: C₁₄H₁₂FNO₂S
• 分子量: 277.319
• InChiKey: VNCIUXNEXOUBBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.5
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(2-fluorobenzoyl)-S-methyl-S-phenylsulfoximine 、 二苯基乙炔 在 silver hexafluoroantimonate 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 copper(II) acetate monohydrate 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以82%的产率得到9-fluoro-5,6,13-triphenyl-8H-isoquinolino[3,2-a]isoquinolin-8-one
  参考文献：
  名称：

  杂芳基的Ru催化一锅径二环化：直接获得π共轭多环酰胺

  摘要：

  报道了具有对称和不对称炔烃的新型Ru催化的杂芳烃的氧化双环。首次展示了使用两个不同的炔烃进行杂芳烃不对称环氧化的一般方法。甲基苯基亚砜亚胺（MPS）在杂芳烃的环空中起重要作用，并允许通过一次操作形成多个C-C和C-N键来构建结构复杂的π-共轭杂芳烃稠合的多环酰胺骨架。该反应表现出优异的底物范围，并能耐受各种官能团。

  DOI：

  10.1021/acs.orglett.6b03314
• 作为产物：
  描述：

  (甲基亚砜亚胺基)苯 在 叔丁基过氧化氢 、 ferrous(II) sulfate heptahydrate 、 N-氯代丁二酰亚胺 作用下， 以 癸烷 、 乙腈 为溶剂， 反应 28.0h， 生成 N-(2-fluorobenzoyl)-S-methyl-S-phenylsulfoximine
  参考文献：
  名称：

  Iron-Catalyzed One-Pot N-Aroylation of NH-Sulfoximines with Methylarenes through Benzylic C–H Bond Oxidation

  摘要：

  An efficient catalytic method has been developed for the synthesis of N-aroylated sulfoximines from readily available toluenes (methylarenes) as source of the aroyl coupling partner and NH-sulfoximines, employing an environmentally benign iron catalyst. This protocol involves oxidation of benzylic C-H bonds of toluenes to generate aroyl radical intermediates followed by oxidative coupling with NH-sulfoximines to form N-aroylated sulfoximines in good to excellent yields. The intermediate aroyl radical is successfully trapped with TEMPO to prove the radical pathway of the reaction.

  DOI：

  10.1055/s-0035-1561402

文献信息

• Interweaving Visible‐Light and Iron Catalysis for Nitrene Formation and Transformation with Dioxazolones
  作者：Jing‐Jing Tang、Xiaoqiang Yu、Yi Wang、Yoshinori Yamamoto、Ming Bao

  DOI：10.1002/anie.202016234

  日期：2021.7.19

  transfer reactions with dioxazolones for intermolecular C(sp3)-N, N=S, and N=P bond formation are described. These reactions occur with exogenous-ligand-free process and feature satisfactory to excellent yields (up to 99 %), an ample substrate scope (109 examples) under mild reaction conditions. In contrast to intramolecular C−H amidations strategies, an intermolecular regioselective C−H amidation via

  本文描述了可见光驱动的铁催化氮烯转移反应与二恶唑酮分子间 C(sp 3 )-N、N=S 和 N=P 键的形成。这些反应在无外源配体的过程中发生，并且具有令人满意的优异产率（高达 99%），在温和的反应条件下具有足够的底物范围（109 个例子）。与分子内 C−H 酰胺化策略相反，设计了通过可见光诱导的氮烯转移反应的分子间区域选择性 C−H 酰胺化。机理研究表明该反应通过自由基途径进行。计算研究表明，二恶唑酮的脱羧取决于通过可见光照射将六重态二恶唑酮结合铁物质转化为四重旋态。
• Ruthenium-Catalyzed <i>ortho</i>-C–H Mono- and Di-imidation of Arenes with <i>N</i>-Tosyloxyphthalimide
  作者：M. Ramu Yadav、Majji Shankar、E. Ramesh、Koushik Ghosh、Akhila K. Sahoo

  DOI：10.1021/acs.orglett.5b00570

  日期：2015.4.17

  The Ru(II)-catalyzed imidation of the o-C–H bond in arenes with N-tosyloxyphthalimide is realized with the assistance of a methyl phenylsulfoximine (MPS) directing group. This method is applicable to access the hitherto difficult o-C–H di-imidation products. The sequential C–N and C–C bond formation of o-C–H arenes creates peripherally decorated benzoic acid derivatives. The readily removable MPS-DG

  N-甲苯磺酰氧基邻苯二甲酰亚胺在Ru（II）催化的芳烃中o -C-H键的酰亚胺化反应是通过甲基苯基亚磺酰亚胺（MPS）导向基团实现的。此方法适用于访问迄今困难的o -C–H二酰亚胺化产品。o -C–H芳烃的顺序C–N和C–C键形成会产生周边装饰的苯甲酸衍生物。易于除去的MPS-DG和易于修饰的邻苯二甲酰部分使该策略对于构建高度官能化的带有CN的芳烃和杂芳烃具有可行性。
• Visible light-induced C–C bond cleavage in a multicomponent reaction cascade allowing acylations of sulfoximines with ketones
  作者：Yongliang Tu、Duo Zhang、Peng Shi、Chenyang Wang、Ding Ma、Carsten Bolm

  DOI：10.1039/d1ob01411k

  日期：——

  Visible light (provided by blue LEDs) induces a very smooth C–C-bond cleavage (analogous to a Norrish Type 1 reaction), which allows to use simple ketones for N-aroylations of sulfoximines.

  可见光（由蓝色LED提供）诱导非常平滑的C-C键断裂（类似于Norrish Type 1反应），这使得可以使用简单的酮对亚砜胺进行N-芳基化。
• Sulfoximine-Directed Ruthenium-Catalyzed <i>ortho</i>-C–H Alkenylation of (Hetero)Arenes: Synthesis of EP3 Receptor Antagonist Analogue
  作者：M. Ramu Yadav、Raja K. Rit、Majji Shankar、Akhila K. Sahoo

  DOI：10.1021/jo5008465

  日期：2014.7.3

  The reusable sulfoximine directing-group-assisted Ru(II)-catalyzed chemo- and regioselective ortho-C-H alkenylation of arenes and heteroarenes with acrylates and alpha,beta-unsaturated ketones/vinyl sulfone is shown. The N-aroyl sulfoximine undergoes annulation with diphenylacetylene, delivering isoquinolinones and methyl phenyl sulfoxide. The present protocol is successfully employed for the synthesis of the EP3 receptor antagonist analogue.
• Sulfoximine Directed Intermolecular <i>o</i>-C–H Amidation of Arenes with Sulfonyl Azides
  作者：M. Ramu Yadav、Raja K. Rit、Akhila K. Sahoo

  DOI：10.1021/ol400411v

  日期：2013.4.5

  The Ru(II)-catalyzed Intermolecular o-C-H amidation of arenes in N-benzoylated sulfoximine with sulfonyl azides is demonstrated. The reaction proceeds with broad substrate scope and tolerates various functional groups. Base hydrolysis of the amidation product provides the anthranilic acid derivatives and methylphenyl sulfoximine (MPS) directing group. This method Is successfully employed for the synthesis of HMR 1766.