rac-N-(phenyl)-S-[4-(bromo)phenyl]-S-methylsulfoximine

• 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: rac-N-(phenyl)-S-[4-(bromo)phenyl]-S-methylsulfoximine
• 英文别名: rac-N-(phenyl)-S-4-bromo-phenyl-S-methylsulfoximine；N-phenyl-S-(4-bromo)phenyl-S-methylsulfoximine；N-phenyl-S-(4-bromophenyl)-S-methylsulfoximine；(4-Bromophenyl)-methyl-oxo-phenylimino-lambda6-sulfane；(4-bromophenyl)-methyl-oxo-phenylimino-λ6-sulfane
• 化学式: C₁₃H₁₂BrNOS
• 分子量: 310.214
• InChiKey: IINJLLOQDKDBAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 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：

  4-溴茴香硫醚 在 叔丁基过氧化氢 、 potassium fluoride 、 sodium azide 、 18-冠醚-6 、 硫酸 、 copper(ll) bromide 作用下， 以 四氢呋喃 、 氯仿 、 水 、 乙腈 为溶剂， 反应 12.0h， 生成 rac-N-(phenyl)-S-[4-(bromo)phenyl]-S-methylsulfoximine
  参考文献：
  名称：

  Metal-Free Approach for the Synthesis of N-Aryl Sulfoximines via Aryne Intermediate

  摘要：

  A metal-free and operationally simple N-arylation of NH-sulfoximines with precursors is reported. Transition metal-free reaction conditions and Shorter reaction times are the highlights of the present method. The mild optimized condition was :also found to be suitable with enantiopure substrates.

  DOI：

  10.1021/acs.orglett.5b02804

文献信息

• 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-Mediated Cross-Coupling Reactions of N-Unsubstituted Sulfoximines and Aryl Halides
  作者：Gae Young Cho、Pauline Rémy、Jenny Jansson、Christian Moessner、Carsten Bolm

  DOI：10.1021/ol048806h

  日期：2004.9.1

  [reaction: see text] Copper-mediated cross-coupling reactions of sulfoximines with aryl iodides and aryl bromides provide N-arylated sulfoximines in high yields. The method is complementary to the known palladium-catalyzed N-arylation and allows the preparation of N-arylated sulfoximines, which have previously been inaccessible.

  [反应：见正文]铜介导的亚砜亚砜与芳基碘化物和芳基溴化物的交叉偶联反应可提供高收率的N-芳基亚砜基亚砜。该方法是对已知的钯催化的N-芳基化的补充，并且允许制备以前难以获得的N-芳基化的亚磺酰亚胺。
• 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.
• Metal-Free Approach for the Synthesis of <i>N</i>-Aryl Sulfoximines via Aryne Intermediate
  作者：Sravan Kumar Aithagani、Saidulu Dara、Gurunadham Munagala、Hariprasad Aruri、Mahipal Yadav、Shweta Sharma、Ram A. Vishwakarma、Parvinder Pal Singh

  DOI：10.1021/acs.orglett.5b02804

  日期：2015.11.20

  A metal-free and operationally simple N-arylation of NH-sulfoximines with precursors is reported. Transition metal-free reaction conditions and Shorter reaction times are the highlights of the present method. The mild optimized condition was :also found to be suitable with enantiopure substrates.