4-[N-(4-fluorophenyl)-S-p-tolylsulfonimidoyl]morpholine

• 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: 4-[N-(4-fluorophenyl)-S-p-tolylsulfonimidoyl]morpholine
• 英文别名: 4-[N-(4-fluorophenyl)-4-methylphenylsulfonimidoyl]morpholine；(4-Fluorophenyl)imino-(4-methylphenyl)-morpholin-4-yl-oxo-lambda6-sulfane；(4-fluorophenyl)imino-(4-methylphenyl)-morpholin-4-yl-oxo-λ6-sulfane
• 化学式: C₁₇H₁₉FN₂O₂S
• 分子量: 334.414
• InChiKey: RLIWENDWGHOFBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  50.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-氟苯硼酸 、 4-(4-methylphenylsulfonimidoyl)morpholine 在 copper diacetate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以86%的产率得到4-[N-(4-fluorophenyl)-S-p-tolylsulfonimidoyl]morpholine
  参考文献：
  名称：

  Cu(OAc)2 promoted Chan–Evans–Lam C–N cross coupling reactions on the N- and N′-nitrogen atoms of sulfonimidamides with aryl boronic acids

  摘要：

  We report a highly efficient and mild protocol for Chan-Evans-Lam C-N cross coupling of sulfonimidamides and aryl boronic acids using Cu(OAc)(2) as mediator, triethylamine (TEA) as base and acetonitrile as solvent. The reaction proceeds at room temperature and provides high to excellent yields for a variety of boronic acids, allowing N-arylation of both N-protected (N-amine nitrogen) and N-deprotected (N'-imine nitrogen) sulfonimidamides. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.06.122

文献信息

• Copper‐Catalyzed Transsulfinamidation of Sulfinamides as a Key Step in the Preparation of Sulfonamides and Sulfonimidamides
  作者：Hao Yu、Zhen Li、Carsten Bolm

  DOI：10.1002/anie.201810548

  日期：2018.11.19

  sulfinamides are prepared by copper‐catalyzed transsulfinamidation of primary sulfinamides with O‐benzoyl hydroxylamines. Subsequent oxidations of the resulting products lead to the corresponding sulfonamides. Treatment of N‐aryl sulfinamides with O‐benzoyl hydroxylamines under copper catalysis provides N‐aryl sulfonimidamides.

  仲或叔磺酰胺是通过伯亚磺酰胺与O-苯甲酰基羟胺的铜催化转磺酰胺化而制备的。所得产物的随后氧化产生相应的磺酰胺。在铜催化下用O-苯甲酰基羟胺处理N-芳基亚磺酰胺可提供N-芳基磺酰亚胺酰胺。
• Cu(OAc)2 promoted Chan–Evans–Lam C–N cross coupling reactions on the N- and N′-nitrogen atoms of sulfonimidamides with aryl boronic acids
  作者：Ganesh C. Nandi、Sudhakar R. Kota、Thavendran Govender、Hendrik G. Kruger、Per I. Arvidsson

  DOI：10.1016/j.tet.2014.06.122

  日期：2014.9

  We report a highly efficient and mild protocol for Chan-Evans-Lam C-N cross coupling of sulfonimidamides and aryl boronic acids using Cu(OAc)(2) as mediator, triethylamine (TEA) as base and acetonitrile as solvent. The reaction proceeds at room temperature and provides high to excellent yields for a variety of boronic acids, allowing N-arylation of both N-protected (N-amine nitrogen) and N-deprotected (N'-imine nitrogen) sulfonimidamides. (C) 2014 Elsevier Ltd. All rights reserved.