Base-Catalyzed Phenol-Mannich Condensation of Preformed Cesium Iminodiacetate. The Direct Synthesis of Calcein Blue AM and Related Acyloxymethyl Esters
Base-Catalyzed Phenol-Mannich Condensation of Preformed Cesium Iminodiacetate. The Direct Synthesis of Calcein Blue AM and Related Acyloxymethyl Esters
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DOI：
10.1021/acs.joc.3c00155
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发表时间：
2023-08-09
影响因子：
3.6
通讯作者：
Livinghouse，Tom
中科院分区：
文献类型：
--
作者：
Mikesell，Logan D.;Livinghouse，Tom
描述了一种快速且高度实用的单烧瓶程序，用于从亚氨基二乙酸和酚类中位置选择性制备（酰氧基）甲基N-（2-羟基苄基）亚氨基二乙酸酯和相关二酯。这种多组分苯酚-曼尼希缩合的关键在于使用亚氨基二乙酸铯作为反应伙伴。该方案已应用于细胞内荧光染料钙黄绿素蓝 AM 的异常直接合成，目前可用的实验和光谱数据很少。
A rapid and highly practical one-flask procedure for thepositionally selectivepreparation of (acyloxy)methylN-(2-hydroxybenzyl)iminodiacetate and related diesters from iminodiacetic acid and phenols is described. The key to this multicomponent phenol-Mannich condensation resides in the use of cesium iminodiacetate as the reaction partner. This protocol has been applied in an unusually direct synthesis of the intracellular fluorescent dye Calcein blue AM, for which scant experimental and spectroscopic data are presently available.