1-(N-phenylphenylsulfonimidoyl)piperidine | 5085-79-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-(N-phenylphenylsulfonimidoyl)piperidine
• 英文别名: Oxo-phenyl-phenylimino-piperidin-1-yl-lambda6-sulfane；oxo-phenyl-phenylimino-piperidin-1-yl-λ6-sulfane
• CAS: 5085-79-0
• 化学式: C₁₇H₂₀N₂OS
• 分子量: 300.425
• InChiKey: FEUUNRNNZXQPLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  41
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  tert-butyl (oxo(phenyl)(piperidin-1-yl)-λ⁶-sulfaneylidene)carbamate 在 copper diacetate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 39.0h， 生成 1-(N-phenylphenylsulfonimidoyl)piperidine
  参考文献：
  名称：

  A mild and efficient copper-catalyzed N-arylation of unprotected sulfonimidamides using boronic acids

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2013.11.084

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。
• Exploration of Novel Chemical Space: Synthesis and in vitro Evaluation of N-Functionalized Tertiary Sulfonimidamides
  作者：Flavia Izzo、Martina Schäfer、Philip Lienau、Ursula Ganzer、Robert Stockman、Ulrich Lücking

  DOI：10.1002/chem.201801557

  日期：2018.7.2

  products are reported. To gain further insight into the properties of sulfonimidamides relevant to medicinal chemistry, a variety of structurally diverse reaction products were tested in selected in vitro assays. The described N‐functionalization reactions provide a short and efficient approach to structurally diverse sulfonimidamides which have been the subject of recent, growing interest in the life

  通过叔 =NH 磺酰亚胺2 aa的各种 N 官能化反应，制备了一组前所未有的结构多样的磺酰亚胺（47 种化合物）。模型化合物2 aa的这些 N 官能化反应包括芳基化、烷基化、三氟甲基化、氰化、磺酰化、烷氧基羰基化（氨基甲酸酯形成）和氨基羰基化（脲形成）。报道了所选 N 功能化产物的小分子 X 射线分析。为了进一步了解磺酰亚胺与药物化学相关的特性，在选定的体外测定中测试了各种结构多样的反应产物。所描述的N-官能化反应为结构多样的磺酰亚胺酰胺提供了一种简短而有效的方法，这已成为生命科学领域最近日益增长的兴趣的主题。
• 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。