N-(4-甲苯磺酰基)-2-(4-甲基苯基)吡咯烷 | 104375-68-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(4-甲苯磺酰基)-2-(4-甲基苯基)吡咯烷
• 英文名称: 2-p-tolyl-1-tosylpyrrolidine
• 英文别名: N-(4-toluenesulfonyl)-2-(4-methylphenyl)pyrrolidine；2-(4-methylphenyl)-1-tosylpyrrolidine；(RS)-1-(toluene-4-sulfonyl)-2-p-tolyl-pyrrolidine；2-(4-Methylphenyl)-1-[(4-methylphenyl)sulfonyl]pyrrolidine；2-(4-methylphenyl)-1-(4-methylphenyl)sulfonylpyrrolidine
• CAS: 104375-68-0
• 化学式: C₁₈H₂₁NO₂S
• 分子量: 315.436
• InChiKey: WRLSSXDFVXDSKD-UHFFFAOYSA-N

物化性质

• 熔点：
  118-120 °C
• 沸点：
  469.4±55.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(4-toluenesulfonyl)-(Z)-4-(4-methylphenyl)but-3-enylamine 在 三氟甲磺酸 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以77%的产率得到N-(4-甲苯磺酰基)-2-(4-甲基苯基)吡咯烷
  参考文献：
  名称：

  Brønsted Acid-Catalyzed Intramolecular Hydroamination of Protected Alkenylamines. Synthesis of Pyrrolidines and Piperidines

  摘要：

  [GRAPHIC]The cyclization of aminoalkenes bearing an electron-withdrawing group on the nitrogen atom was catalyzed by triflic or sulfuric acid in toluene. Pyrrolidines and piperidines were formed in excellent yields. N-Phenylanilides also underwent cyclization to form gamma-lactams.

  DOI：

  10.1021/ol025659j

文献信息

• Gold- and Silver-Catalyzed Tandem Amination/Ring Expansion of Cyclopropyl Methanols with Sulfonamides as an Expedient Route to Pyrrolidines
  作者：Weidong Rao、Philip Wai Hong Chan

  DOI：10.1002/chem.200801242

  日期：2008.11.17

  An efficient synthetic route to pyrrolidines that relies on AuCl/AgOTf-catalyzed tandem amination/ring expansion of substituted cyclopropyl methanols with sulfonamides is reported herein. The reactions proceed rapidly at 100 degrees C with catalyst loadings as low as 2 mol % and produce the pyrrolidine products in yields of 30-95 %. The method was shown to be applicable to a broad range of cyclopropyl

  本文报道了依赖于AuCl / AgOTf催化的串联磺胺化/取代的环丙基甲醇与磺酰胺的环吡咯烷酮的有效合成途径。反应在100℃下以低至2mol％的催化剂负载快速进行，并以30-95％的产率产生吡咯烷产物。已证明该方法适用于多种环丙基甲醇，包括未活化的环丙基甲醇和含有吸电子，给电子和空间需求取代基的磺酰胺底物。提示该机理涉及通过AuCl / AgOTf催化剂活化醇底物，然后使原料电离，这引起环丙烷部分的开环并被磺酰胺亲核试剂捕获。
• 1-arenesulfonyl-2-aryl-pyrrolidine and pyridine derivatives
  申请人：Hoffmann- La Roche Inc.

  公开号：US06284785B1

  公开（公告）日：2001-09-04

  1-Arenesulfonyl-2-Aryl-pyrrolidine and pyridine derivatives having activity as ligands of metabotropic glutamate receptors of the formula are disclosed.

  本发明揭示了具有代谢型谷氨酸受体配体活性的公式为1-芳烃磺酰基-2-芳基吡咯烷和吡啶衍生物。
• Palladium-catalyzed inter- and intramolecular hydroamination of styrenes coupled with alcohol oxidation using N-fluorobenzenesulfonimide as the oxidant
  作者：Tao Xu、Shuifa Qiu、Guosheng Liu

  DOI：10.1016/j.jorganchem.2010.07.015

  日期：2011.1

  Palladium-catalyzed inter- and intramolecular hydroaminations of styrenes that are coupled to alcohol oxidation under oxidative condition are reported. The fluorination reagent NFSI is used as the nitrogen source as well as the oxidant. Bidental nitrogen ligand bathocuproine plays a crucial role in this transformation. (C) 2010 Elsevier B.V. All rights reserved.
• Gold(I)-Catalyzed Domino Ring-Opening Ring-Closing Hydroamination of Methylenecyclopropanes (MCPs) with Sulfonamides:  Facile Preparation of Pyrrolidine Derivatives
  作者：Min Shi、Le-Ping Liu、Jie Tang

  DOI：10.1021/ol0614830

  日期：2006.8.1

  Reaction of methylenecyclopropanes 1 with sulfonamides produces the corresponding pyrrolidine derivatives 3 in moderate to good yields under the catalysis of Au(I) via a domino ring-opening ring-closing hydroamination process.
• Synthesis of five- and six-membered nitrogen heterocycles via palladium(II)-catalyzed cyclization of unsaturated amides
  作者：Yoshinao Tamaru、Makoto Hojo、Shinichi Kawamura、Zenichi Yoshida

  DOI：10.1021/jo00371a041

  日期：1986.10