N-(2,4,6-trimethylphenyl)-S,S-methylphenylsulfoximine | 1200799-52-5

• 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-(2,4,6-trimethylphenyl)-S,S-methylphenylsulfoximine
• 英文别名: Methyl-oxo-phenyl-(2,4,6-trimethylphenyl)imino-lambda6-sulfane；methyl-oxo-phenyl-(2,4,6-trimethylphenyl)imino-λ6-sulfane
• CAS: 1200799-52-5
• 化学式: C₁₆H₁₉NOS
• 分子量: 273.399
• InChiKey: PFQQHUXRMAKBGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-溴戊酸乙酯 、 N-(2,4,6-trimethylphenyl)-S,S-methylphenylsulfoximine 在 正丁基锂 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.5h， 以31%的产率得到(E)-(mesitylimino)(phenyl)((tetrahydro-2H-pyran-2-ylidene)methyl)-l6-sulfanone
  参考文献：
  名称：

  Consecutive reactions with sulfoximines: a direct access to 2-sulfonimidoylylidene tetrahydrofurans and 6-sulfonimidoylmethyl-3,4-dihydro-2H-pyrans

  摘要：

  2-Sulfonimidoylylidene tetrahydrofurans and 2-sulfonimidoylylidene-5-vinyl tetrahydrofurans were readily synthesized via a consecutive acylation/SN2 sequence with total regio- and chemoselectivity from Johnson's sulfoximine derivatives. The same consecutive reaction could also be applied to the expeditious synthesis of 6-sulfonimidoylmethyl-3,4-dihydro-2H-pyrans. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.080
• 作为产物：
  描述：

  2-溴-1,3,5-三甲基苯 、 (甲基亚砜亚胺基)苯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium tert-butylate 、 1,3-双(2,6-二异丙基苯基)氯化咪唑鎓 作用下， 以 1,4-二氧六环 为溶剂， 以96%的产率得到N-(2,4,6-trimethylphenyl)-S,S-methylphenylsulfoximine
  参考文献：
  名称：

  Consecutive reactions with sulfoximines: a direct access to 2-sulfonimidoylylidene tetrahydrofurans and 6-sulfonimidoylmethyl-3,4-dihydro-2H-pyrans

  摘要：

  2-Sulfonimidoylylidene tetrahydrofurans and 2-sulfonimidoylylidene-5-vinyl tetrahydrofurans were readily synthesized via a consecutive acylation/SN2 sequence with total regio- and chemoselectivity from Johnson's sulfoximine derivatives. The same consecutive reaction could also be applied to the expeditious synthesis of 6-sulfonimidoylmethyl-3,4-dihydro-2H-pyrans. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.080

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。