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4-Nitrophenyl Chloroformate: A Versatile Coupling Reagent
Synlett ( IF 1.7 ) Pub Date : 2009-10-23 , DOI: 10.1055/s-0029-1218291
Benedikt Sammet

4-Nitrophenyl chloroformate (4-NPC; CAS: 7693-46-1) is one of the most common reagents for the activation of alcohols, thiols and amines for the formation of carbonates and carbamates. It is a colorless, crystalline solid, which is easy to handle and well-storable. It was introduced into literature for the synthesis of t-butyl 4-nitrophenyl carbonate as a reagent for the Boc-protection of amines. [¹] Today, however, its range of application is very broad and has led to considerably safer chemistry, replacing phosgene in many reactions. The obtained 4-NP carbonates and carbamates are often stable and can be purified by column chromatography or recrystallization. Nevertheless, one-pot procedures for the in situ substitution of the 4-nitrophenyl moiety are regularly employed. Due to the increasing demand for bioconjugates containing different natural product classes, stable carbonate and carbamate linker systems are conveniently synthesized by applying this reagent. [²] In addition, the substance is used for covalent protein immobilization on surfaces [³] and polymer peptide linkages. [4]



中文翻译:

4-硝基苯基氯甲酸酯:一种多功能偶联剂

氯甲酸4-硝基苯酯(4-NPC; CAS:7693-46-1)是用于活化醇,硫醇和胺以形成碳酸盐和氨基甲酸酯的最常用试剂之一。它是一种无色结晶固体,易于处理且易于储存。将其引入用于合成丁基碳酸4-硝基苯酯作为胺的Boc保护试剂的文献中。[ ¹然而,今天,它的应用范围非常广泛,并导致了相当安全的化学反应,在许多反应中代替了光气。所获得的4-NP碳酸盐和氨基甲酸酯通常是稳定的,可以通过柱色谱法或重结晶法纯化。然而,通常使用一锅法原位取代4-硝基苯基部分。由于对包含不同天然产物类别的生物缀合物的需求不断增加,因此通过应用该试剂可方便地合成稳定的碳酸盐和氨基甲酸酯连接体系。[ ² ]此外,该物质还用于将共价蛋白固定在表面[ ³ ]和聚合物肽键上。[ 4 ]

更新日期:2009-10-23
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