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。
• 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
• Brønsted Acid-Catalyzed Intramolecular Hydroamination of Protected Alkenylamines. Synthesis of Pyrrolidines and Piperidines
  作者：Björn Schlummer、John F. Hartwig

  DOI：10.1021/ol025659j

  日期：2002.5.1

  [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.