N-(p-nitrobenzenesulfonyl)-aziridine-2-carboxylic acid

• 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-(p-nitrobenzenesulfonyl)-aziridine-2-carboxylic acid
• 英文别名: N-nosylaziridine-2-carboxylic acid；1-(4-nitrophenyl)sulfonylaziridine-2-carboxylic acid
• 化学式: C₉H₈N₂O₆S
• 分子量: 272.238
• InChiKey: POMFFIUIYUKHPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  129
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl 1-((4-nitrophenyl)sulfonyl)aziridine-2-carboxylate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 生成 N-(p-nitrobenzenesulfonyl)-aziridine-2-carboxylic acid
  参考文献：
  名称：

  Aminolysis of Resin-Bound N-Nosylaziridine-2-carboxylic Acids

  摘要：

  Solid-phase synthesis is a rapidly developing area of organic chemistry, of particular importance for medicinal chemistry and chemical biology. Aziridines have previously only rarely been applied in solid-phase synthesis. In the present work, aminolysis of resin-bound, spring-loaded N-nitrobenzenesulfonyl-activated aziridine-2-carboxylic acids has been optimized and employed in the synthesis of a number of open-chain and heterocyclic scaffolds, including enantiopure products.

  DOI：

  10.1021/ol061304e

文献信息

• [EN] PROCESS FOR THE PREPARATION OF 2-[2-(2-AMINO-2-CARBOXY-ETHYLAMINO)-2-CARBOXY-ETHYLAMINO]-SUCCINIC ACID (AM-A) AND ANALOGS AND DERIVATIVES THEREOF<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION D'ACIDE 2-[2-(2-AMINO-2-CARBOXY-ÉTHYLAMINO)-2-CARBOXY-ÉTHYLAMINO]-SUCCINIQUE (AM-A) ET DES ANALOGUES ET DÉRIVÉS DE CELUI-CI
  申请人：UNIV MCMASTER

  公开号：WO2017070794A1

  公开（公告）日：2017-05-04

  The present application relates to processes for the preparation of the aspergillomarasmine A (AM-A) compound and analogs and derivatives thereof. The features of this process involves the use of a cyclic activated serine synthon in the construction of the poly-amino acid backbone. Also included are certain novel analogs of AM-A along with compositions comprising these compounds and uses thereof.
• Aminolysis of Resin-Bound <i>N</i>-Nosylaziridine-2-carboxylic Acids
  作者：Christian A. Olsen、Caspar Christensen、Birgitte Nielsen、Mohamed M. Farah、Matthias Witt、Rasmus P. Clausen、Jesper L. Kristensen、Henrik Franzyk、Jerzy W. Jaroszewski

  DOI：10.1021/ol061304e

  日期：2006.7.1

  Solid-phase synthesis is a rapidly developing area of organic chemistry, of particular importance for medicinal chemistry and chemical biology. Aziridines have previously only rarely been applied in solid-phase synthesis. In the present work, aminolysis of resin-bound, spring-loaded N-nitrobenzenesulfonyl-activated aziridine-2-carboxylic acids has been optimized and employed in the synthesis of a number of open-chain and heterocyclic scaffolds, including enantiopure products.