N-(4-chlorophenyl)-S-methyl-S-phenylsulfoximine | 56158-15-7

• 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-chlorophenyl)-S-methyl-S-phenylsulfoximine
• 英文别名: [(4-Chlorophenyl)imino](methyl)phenyl-lambda6-sulfanone；(4-chlorophenyl)imino-methyl-oxo-phenyl-λ6-sulfane
• CAS: 56158-15-7
• 化学式: C₁₃H₁₂ClNOS
• 分子量: 265.763
• InChiKey: KMWBPZPYEAXRFF-UHFFFAOYSA-N

物化性质

• 熔点：
  64-66 °C
• 沸点：
  403.6±47.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

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：

  (±)-N-(4-chlorophenyl)methanesulfinamide 在 亚碘酰苯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 N-(4-chlorophenyl)-S-methyl-S-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 N-Arylation of Sulfoximines with Arylboronic Acids under Mild Conditions
  作者：Surabhi Gupta、Siddharth Baranwal、Nalluchamy Muniyappan、Shahulhameed Sabiah、Jeyakumar Kandasamy

  DOI：10.1055/s-0037-1612216

  日期：2019.5

  optimized reaction conditions are well suited to the task of N-vinylation of sulfoximine with trans-2-phenylvinylboronic acid. N-Arylation of sulfoximines with different arylboronic acids, including sterically hindered boronic acids, is achieved using copper(I) iodide and 4-DMAP at room temperature. Moreover, N-arylation of biologically relevant l-methionine sulfoximine is demonstrated for the first time

  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。
• 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。
• N-Arylated Sulfoximines as Cross-Coupling Building Blocks
  作者：Anne-Katrin Bachon、Anne-Dorothee Steinkamp、Carsten Bolm

  DOI：10.1002/adsc.201701394

  日期：2018.3.20

  The application of borylated N‐aryl sulfoximines as newly designed synthetic building blocks in Suzuki‐type cross coupling reactions offers rapid access to a wide range of N‐biaryl derivatives with potential relevance for medicinal chemistry and crop protection in good to excellent yields (up to 98%).

  在Suzuki型交叉偶联反应中应用硼化的N-芳基亚砜亚胺作为新设计的合成构件，可以快速获得广泛的N-联芳基衍生物，对药物化学和作物保护具有潜在的相关性，且产量高至优异（可达98％）。
• 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.