N,N-dimethyl 1-(p-tolylsulfonyl)aziridine-2-carboxamide | 193634-85-4

• 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: N,N-dimethyl 1-(p-tolylsulfonyl)aziridine-2-carboxamide
• 英文别名: N,N-dimethyl-1-(p-tolylsulfonyl)aziridine-2-carboxamide；N,N-dimethyl-(1'-tosylaziridin-2'-yl)carboxamide；N,N-dimethyl-1-(4-methylphenyl)sulfonylaziridine-2-carboxamide
• CAS: 193634-85-4
• 化学式: C₁₂H₁₆N₂O₃S
• 分子量: 268.337
• InChiKey: MMYDHQBMHTXFSU-UHFFFAOYSA-N

物化性质

• 沸点：
  440.6±55.0 °C(Predicted)
• 密度：
  1.322±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  65.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl 1-(p-tolylsulfonyl)aziridine-2-carboxamide 在 N,N-二甲基乙醇胺 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以86%的产率得到3-(p-methylphenylsulfonylamino)-N,N-(dimethyl)propanamide
  参考文献：
  名称：

  Reduction of 2-Acylaziridines by Samarium(II) Iodide. An Efficient and Regioselective Route to β-Amino Carbonyl Compounds.

  摘要：

  DOI：

  10.1016/s0040-4020(97)00576-0
• 作为产物：
  描述：

  N,N-二甲基丙烯酰胺 、 [(N-tosylimino)iodo]benzene 在 tetrakis(acetonitrile)copper(I) perchlorate 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以87%的产率得到N,N-dimethyl 1-(p-tolylsulfonyl)aziridine-2-carboxamide
  参考文献：
  名称：

  Reduction of 2-Acylaziridines by Samarium(II) Iodide. An Efficient and Regioselective Route to β-Amino Carbonyl Compounds.

  摘要：

  DOI：

  10.1016/s0040-4020(97)00576-0

文献信息

• Aziridine-2-carboxylic acid derivatives and its open-ring isomers as a novel PDIA1 inhibitors
  作者：Irena Leite、Victor Andrianov、Diana Zelencova-Gopejenko、Einars Loza、Iveta Kazhoka-Lapsa、Ilona Domracheva、Marta Stoyak、Stefan Chlopicki、Ivars Kalvins

  DOI：10.1007/s10593-021-03034-x

  日期：2021.11

  Acyl derivatives of aziridine-2-carboxylic acid have been synthesized and tested as PDIA1 inhibitors. Calculations of charge value and distribution in aziridine ring system and some alkylating agents were performed. For the first time was found that acyl derivatives of aziridine-2-carboxylic acid are weak to moderately active PDIA1 inhibitors.

  氮丙啶-2-羧酸的酰基衍生物已被合成并作为 PDIA1 抑制剂进行测试。进行了氮丙啶环系统和一些烷化剂的电荷值和分布的计算。首次发现氮丙啶-2-羧酸的酰基衍生物是弱到中等活性的PDIA1抑制剂。
• Palladium(ii)-promoted aziridination of olefins with bromamine T as the nitrogen transfer reagent
  作者：Alexandra M. M. Antunes、Susana J. L. Marto、Paula S. Branco、Sundaresan Prabhakar、Ana M. Lobo

  DOI：10.1039/b008701g

  日期：——

  The palladium(II)-promoted reaction of a variety of olefins and bromamine T, as the nitrogen atom transfer reagent, provided N-tosyl-2-substituted aziridines under mild conditions.

  钯（II）促进的多种烯烃与溴胺T作为氮原子转移试剂的反应，在温和条件下生成了N-托烷磺酰-2-取代的氮杂环。
• [EN] AROMATIC SULPHONAMIDES DERIVATIVES THAT INHIBITS PDI A1, THEIR SYNTHESIS AND USE<br/>[FR] DÉRIVÉS DE SULFONAMIDES AROMATIQUES INHIBANT PDI A1, LEUR SYNTHÈSE ET LEUR UTILISATION
  申请人：UNIV JAGIELLONSKI

  公开号：WO2021141506A1

  公开（公告）日：2021-07-15

  The invention relates to a new group of aromatic sulphonamides derivatives of formula (I) and their synthesis and use for modulation of the activity of protein disulfide isomerase (PDI). More particularly, the invention provides small molecule inhibitors of PDI A1 that display antiplatelet, antithrombotic and anticancer activities.

  本发明涉及一种新的芳香磺酰胺衍生物组，其化学式为(I)，以及它们的合成和用于调节蛋白质二硫键异构酶（PDI）活性的用途。更具体地说，本发明提供了PDI A1的小分子抑制剂，具有抗血小板、抗血栓和抗癌活性。
• [EN] AROMATIC SULPHONAMIDES DERIVATIVES THAT INHIBITS PDI A3, THEIR SYNTHESIS AND USE<br/>[FR] DÉRIVÉS DE SULFONAMIDES AROMATIQUES INHIBANT PDI A3, LEUR SYNTHÈSE ET LEUR UTILISATION
  申请人：UNIV JAGIELLONSKI

  公开号：WO2021141507A1

  公开（公告）日：2021-07-15

  The invention relates to a new group of aromatic sulphonamides derivatives of formula (I) and their synthesis and use for modulation of the activity of protein disulfide isomerase (PDI). More particularly, the invention provides small molecule inhibitors of PDI A3 that display antiplatelet, antithrombotic and anticancer activities.

  本发明涉及一类新的芳香基磺酰胺衍生物组，其化学式为(I)，以及它们的合成和用于调节蛋白二硫键异构酶（PDI）活性的用途。更具体地，本发明提供了PDI A3的小分子抑制剂，具有抗血小板、抗血栓和抗癌活性。
• Copper‐Catalyzed Heterocyclic Recombination of Aziridine and Diazetidine for the Synthesis of Imidazolidine**
  作者：Daiki Higuchi、Satoshi Matsubara、Hiroki Kadowaki、Daisuke Tanaka、Kei Murakami

  DOI：10.1002/chem.202301071

  日期：2023.8

  goal in organic synthesis. Herein, the Cu-catalyzed synthesis of imidazolidine through heterocyclic recombination between aziridine and diazetidine is presented. The scope is sufficiently broad to form various imidazolidines, since the reaction conditions are suitable for many functional groups.Copper-Catalyzed Heterocyclic Recombination of Aziridine and Diazetidine for the Synthesis of Imidazolidine

  发现金属新的催化应用仍然是有机合成的一个重要目标。在此，提出了通过氮丙啶和二氮杂环丁烷之间的杂环重组，铜催化合成咪唑烷。由于反应条件适合许多官能团，其范围足够广泛，可以形成各种咪唑烷。铜催化氮丙啶和二氮杂环丁烷的杂环重组用于合成咪唑烷（Murakami 等人）