4-(9-fluorenylmethyloxycarbonyl)phenylhydrazine (FmPH): a new chromophoric reagent for quantitative monitoring of solid-phase aldehydes(1-3).
4-(9-fluorenylmethyloxycarbonyl)phenylhydrazine (FmPH): a new chromophoric reagent for quantitative monitoring of solid-phase aldehydes(1-3).
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4-(9-芴甲氧基羰基)苯肼 (FmPH)：一种用于固相醛定量监测的新型发色试剂 (1-3)。
DOI：
10.1021/jo049830b
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发表时间：
2004
期刊：
影响因子：
--
通讯作者：
Barany,George
中科院分区：
文献类型：
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作者：
Shannon,SimonK;Barany,George
使用新试剂 4-(9-芴基甲氧基羰基)苯肼 (FmPH) 开发了一种定量固相醛的直接方法。 FmPH 试剂由市售对肼苯甲酸分三步合成（总收率 24%）。在原甲酸三甲酯 (TMOF) 作为脱水剂的情况下，树脂结合的醛与 FmPH 进行定量反应，形成高度共轭的固定化 FmPH-腙。接下来，用过量的哌啶-N,N-二甲基甲酰胺 (1:1) 温和处理腙，从载体上释放哌啶-二苯并富烯加合物发色团 (ε301nm= 7800 M-1cm-1)。醛的 FmPH 定量被证明是一种直接、灵敏且可重复的技术，用于监测树脂结合的醛（尽管其反应性不足以对酮进行可靠的定量）。 FmPH 醛测定适用于一系列固体支持物，特别适用于聚（乙二醇）-聚苯乙烯 (PEG-PS)、氨甲基聚苯乙烯 (AMP) 和交联乙氧基化丙烯酸酯树脂 (CLEAR)。
A direct method for quantifying solid-phase aldehydes has been developed, using a new reagent, 4-(9-fluorenylmethyloxycarbonyl)phenylhydrazine (FmPH). The FmPH reagent was synthesized in three steps (24% overall yield) from commercially availablep-hydrazinobenzoic acid. Resin-bound aldehydes reacted quantitatively with FmPH, in the presence of trimethylorthoformate (TMOF) as a dehydrating agent, to form a highly conjugated, immobilized FmPH-hydrazone. Next, mild treatment of the hydrazone with an excess of piperidine−N,N-dimethylformamide (1:1) released the piperidine−dibenzofulvene adduct chromophore (ε301nm= 7800 M-1cm-1) from the support. FmPH quantitation of aldehydes proved to be a straightforward, sensitive, and reproducible technique for monitoring resin-bound aldehydes [albeit insufficiently reactive to allow reliable quantification of ketones]. The FmPH aldehyde assay is applicable to a range of solid supports, as demonstrated specifically for poly(ethylene glycol)-polystyrene (PEG-PS), aminomethylpolystyrene (AMP), and cross-linked ethoxylate acrylate resin (CLEAR).