V2EX tosyl chloride

Tosyl Chloride

定义 Definition

对甲苯磺酰氯(常写作 TsCl),一种常用的有机合成试剂,主要用于把醇(ROH)转化为对甲苯磺酸酯(tosylate, ROTs),从而把羟基变成更好的离去基;也可用于某些胺、杂环等的磺酰化反应。(该词也常出现在“保护/活化羟基”“亲核取代”等语境中。)

发音 Pronunciation (IPA)

/tsl klrad/(也常见 /tsl klrad/)

例句 Examples

Tosyl chloride is used to convert alcohols into tosylates.
对甲苯磺酰氯用于把醇转化为对甲苯磺酸酯。

After treating the secondary alcohol with tosyl chloride and pyridine, the product underwent an SN2 substitution with sodium azide.
用对甲苯磺酰氯和吡啶处理该二级醇后,产物又与叠氮化钠发生了 SN2 取代反应。

词源 Etymology

Tosyl 来自 p-toluenesulfonyl(对甲苯磺酰基,常用缩写 Ts),而 chloride 表示其“氯化物”形式:对甲苯磺酰氯(p-toluenesulfonyl chloride)。因此 tosyl chloride 字面意思就是“对甲苯磺酰基的氯化物”。

相词 Related Words

文学与著作 Notable Works

  • Organic Chemistry(Clayden, Greeves & Warren):在“将醇转化为良好离去基/磺酸酯化”章节中常提及 TsCl。
  • Protective Groups in Organic Synthesis(Greene & Wuts):在醇的衍生化与保护基策略中频繁出现。
  • March’s Advanced Organic Chemistry:在亲核取代与官能团转化的机理讨论中常用 TsCl 作为经典试剂示例。
  • Organic Syntheses(期刊/丛书):多条实验步骤中会使用对甲苯磺酰氯进行活化或制备磺酸酯。
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