1-(p-tolylsulfonyl)aziridine-2-carbonitrile | 20588-32-3

• 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: 1-(p-tolylsulfonyl)aziridine-2-carbonitrile
• 英文别名: 1-(4-Methylphenyl)sulfonylaziridine-2-carbonitrile
• CAS: 20588-32-3
• 化学式: C₁₀H₁₀N₂O₂S
• 分子量: 222.268
• InChiKey: NHDPDKLSWPSYCR-UHFFFAOYSA-N

物化性质

• 沸点：
  418.6±55.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  69.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(p-tolylsulfonyl)aziridine-2-carbonitrile 在 甲醇 、 magnesium 作用下， 反应 2.0h， 以83%的产率得到N-(2-cyanoethyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Regiospecific Reductive Cleavage of the C(2)−N Bond of Aziridines Substituted with an Electron Acceptor Mediated by Mg/MeOH

  摘要：

  DOI：

  10.1021/jo9806963
• 作为产物：
  描述：

  bromamine T 在 Pd(MeCN)3Cl₂ sodium hydride 作用下， 以 乙腈 为溶剂， 生成 1-(p-tolylsulfonyl)aziridine-2-carbonitrile
  参考文献：
  名称：

  Palladium(ii)-promoted aziridination of olefins with bromamine T as the nitrogen transfer reagent

  摘要：

  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。

  DOI：

  10.1039/b008701g

文献信息

• Synthesis of Functionalized<i>N</i>‐Arylsulfonyl Aziridines from α,β‐Unsaturated Esters, Amides, Ketones, and Nitriles Using<i>N</i>,<i>N</i>‐Dichloroarylsulfonamides as Nitrogen Source
  作者：Upender K. Nadir、Anamika Singh

  DOI：10.1081/scc-120030324

  日期：2004.12.31

  process has been developed for the synthesis of functionalized N‐arylsulfonylaziridines bearing an alkoxycarbonyl, acyl, cyano, and carboxamide group at C2. The two‐step sequence involves addition of N,N‐dichloroarylsulfonamide to the appropriate olefin in the presence of Cu(acac)2, treatment of the resultant chlorosulfonamide with Na2SO3, followed by cyclization with NaOH to give the appropriate aziridine

  摘要 已经开发了一种方便和通用的氮丙啶化方法，用于合成在 C2 上带有烷氧基羰基、酰基、氰基和甲酰胺基团的功能化 N-芳基磺酰基氮丙啶。两步序列包括在 Cu(acac)2 存在下将 N,N-二氯芳基磺酰胺加成到合适的烯烃中，用 Na2SO3 处理所得氯磺酰胺，然后用 NaOH 环化，以良好的收率得到合适的氮丙啶。发现该反应是一种反立体选择性。
• [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。
• Application of the Evans aziridination procedure to 2-substituted acrylates and cinnamates: An expedient route to α-substituted α- and β-amino acids
  作者：Philippe Dauban、Robert H. Dodd

  DOI：10.1016/s0040-4039(98)01132-0

  日期：1998.8

  Reaction of the title compounds with Phl=NSO2Ar (Ar = p-tolyl or p-nitrophenyl) in the presence of catalytic copper (II) triflate in acetonitrile gave the corresponding 2 and/or 3-substituted aziridine-2-carboxylates in generally; good yields. The latter, on reaction with nucleophiles, gave alpha-substituted alpha- or beta-amino acids depending on the pattern of substitution on the aziridine ring. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Titanium Tetraiodide Mediated Reductive Opening of Aziridines, Leading to the Aldol and Mannich-Type Reactions
  作者：Makoto Shimizu、Hiroshi Kurokawa、Shuji Nishiura、Iwao Hachiya

  DOI：10.3987/com-06-s(w)9

  日期：——

  Reductive ring-opening of N-tosylazirindes was readily carried out with titanium tetraicidide to form the titanium enolates, which in turn were subjected to addition reaction with aldehydes or imines to give aldol or Mannich-type products in good yields.