4-(N-phenylphenylsulfonimidoyl)morpholine | 5024-02-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 4-(N-phenylphenylsulfonimidoyl)morpholine
• 英文别名: Morpholin-4-yl-oxo-phenyl-phenylimino-lambda6-sulfane；morpholin-4-yl-oxo-phenyl-phenylimino-λ6-sulfane
• CAS: 5024-02-2
• 化学式: C₁₆H₁₈N₂O₂S
• 分子量: 302.397
• InChiKey: LGPUDQJVQXRYIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  50.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  benzenesulfinamide 在 N-氯代丁二酰亚胺 、 正丁基锂 、 chloro-(2-dicyclohexylphosphino-2’,6’-diisopropoxy-1,1‘-biphenyl)[2-(2-aminoethyl)phenyl] palladium(ll) methyl-tert-butyl ether adduct 、 三氟乙酸 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 47.83h， 生成 4-(N-phenylphenylsulfonimidoyl)morpholine
  参考文献：
  名称：

  Synthesis and arylation of unprotected sulfonimidamides

  摘要：

  Herein we evaluate different methodologies for the synthesis of unprotected sulfonimidamides. Three different procedures that allow orthogonal deprotection of the imine nitrogen under acidic, nucleophilic, and basic conditions were established. Moreover, we present a highly efficient methodology for functionalization of the imine nitrogen through Pd-catalyzed C-N arylation. RuPhos ligand was shown to allow short reaction time, excellent yields, and allowed coupling of both aryl halides and heteroaryl bromides. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.072

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。
• The Preparation of Iminosulfonic Acid Derivatives by Means of Sulfinamides and<i>N</i>-Bromosuccinimide
  作者：Hisashi Takei、Itaru Watanabe、Teruaki Mukaiyama

  DOI：10.1246/bcsj.38.1989

  日期：1965.11

  It has been found that N-substituted benzenesulfinamides (I) react with thionyl chloride to give benzenesulfinyl chloride and the corresponding N-sulfinylamines, and that they are oxidized by treatment with bromine in an alkaline solution to give N-substituted sulfonamides. When these benzenesulfinamides are treated with bromine or N-bromosuccinimide (NBS) in the presence of various primary or secondary

  已经发现N-取代的苯亚磺酰胺(I)与亚硫酰氯反应生成苯亚磺酰氯和相应的N-亚磺酰胺，并且通过在碱性溶液中用溴处理将它们氧化生成N-取代的磺酰胺。当这些苯亚磺酰胺在各种伯胺或仲胺的存在下用溴或 N-溴代琥珀酰亚胺 (NBS) 处理时，可以高产率地获得相应的苯亚氨基磺酰胺。类似地，I、NBS 和对硝基苯酚钠或苯甲酸钠的反应产生对硝基苯基苯亚氨基磺酸盐或 N-苯甲酰基苯磺酰胺。这些反应被认为是通过亚磺酰胺与溴或 NBS 氧化形成的苯亚氨基磺酰溴进行的。
• 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。
• N-Arylation of primary and tertiary sulfonimidamides (SIAs) with benzyne precursors under transition metal-free conditions
  作者：Srinivas Ambala、Kimberleigh B. Govender、Kamal K. Rajbongshi、Thavendran Govender、Hendrik G. Kruger、Tricia Naicker、Per I. Arvidsson

  DOI：10.1016/j.tetlet.2023.154583

  日期：2023.7

  Herein, we report an effective and efficient transition metal-free method wherein benzyne intermediates from silyl aryl triflates were successfully coupled with primary sulfonimidamides. The use of CsF in ACN proved to be the optimal condition for the N-arylation of various substituted primary sulfonimidamides, resulting in good to excellent yields. Further, the addition of 18-crown-6 to the present

  在此，我们报告了一种有效且高效的无过渡金属方法，其中来自甲硅烷基芳基三氟甲磺酸酯的苯炔中间体成功地与伯磺酰亚胺偶联。在 ACN 中使用 CsF 被证明是各种取代的伯磺酰亚胺酰胺的N-芳基化的最佳条件，从而产生良好到极好的收率。此外，在本方法中添加 18-crown-6 将范围扩展到以中低产率获得的叔磺酰亚胺。
• A mild and efficient copper-catalyzed N-arylation of unprotected sulfonimidamides using boronic acids
  作者：S.R.K. Battula、G.V. Subbareddy、I.E. Chakravarthy

  DOI：10.1016/j.tetlet.2013.11.084

  日期：2014.1

  An efficient and low cost copper catalyzed system for N-arylation of sulfonimidamides has been developed. The reaction proceeds at room temperature under base free conditions. Various N-aryl, N-heteroaryl, and N-cyclopropyl sulfonimidamides were obtained in good to excellent yields. (C) 2013 Elsevier Ltd. All rights reserved.