N-phenyl-S-methyl-S-(4-methyl)phenylsulfoximine | 1374007-19-8

• 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-phenyl-S-methyl-S-(4-methyl)phenylsulfoximine
• 英文别名: (±)-Methyl(phenylimino)(p-tolyl)-λ⁶-sulfanone；N-phenyl-S-(4-methylphenyl)-S-methylsulfoximine；methyl(phenylimino)(p-tolyl)-λ⁶-sulfanone；Methyl-(4-methylphenyl)-oxo-phenylimino-lambda6-sulfane；methyl-(4-methylphenyl)-oxo-phenylimino-λ6-sulfane
• CAS: 1374007-19-8
• 化学式: C₁₄H₁₅NOS
• 分子量: 245.345
• InChiKey: VOSFNUPYRRXWLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  (±)-N-phenylmethanesulfinamide 在 亚碘酰苯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 N-phenyl-S-methyl-S-(4-methyl)phenylsulfoximine
  参考文献：
  名称：

  磺酰亚胺盐：通过C–S键形成的磺胺嘧啶合成有用的中间体

  摘要：

  医药上相关的亚砜肟类可从亚磺酰胺盐与市售有机镁试剂的CS偶联中获得。磺酰亚胺盐可通过容易获得的亚磺酰胺的氧化烷氧基化方便地合成。这构成了合成亚砜肟类的常规C–S偶联方法。

  DOI：

  10.1021/acs.orglett.8b01473

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。
• Copper-Catalyzed Ultrasound-Expedited N-Arylation of Sulfoximines using Diaryliodonium Salts
  作者：Buchireddy Vaddula、John Leazer、Rajender S. Varma

  DOI：10.1002/adsc.201100808

  日期：2012.4.16

  An ultrasound‐accelerated route for an expeditious N‐arylation of NH‐sulfoximines is described that involves the use of diaryliodonium salts in aqueous polyethylene glycol‐400 and copper(I) bromide as catalyst at room temperature. The high yields of the products and simple work‐up are the highlights of the protocol.

  本文介绍了一种超声波加速NH-亚砜肟亚胺N-芳基化的方法，该方法涉及在室温下在聚乙二醇400和溴化铜（I）水溶液中使用二芳基碘鎓盐作为催化剂。该产品的重点是产品的高产量和简单的后处理。
• Ultrafast <i>N</i>-arylation of sulfoximines enabled by micellar catalysis in water
  作者：Mingyu Song、Lei Zhang、Diandian Wei、Yu He、Jiajia Jia、Heng Li、Bingxin Yuan

  DOI：10.1039/d2gc01919a

  日期：——

  Sustainable and ultrafast N-arylation of sulfoximines in water enabled by micellar catalysis.

  在胶束催化的水相条件下，实现了持续和超快速的亚磺酰亚胺的N-芳基化。
• 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。
• 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.