碱催化预先形成的亚氨基二乙酸铯的苯酚-曼尼希缩合反应。钙黄绿素蓝AM及相关酰氧基甲基酯的直接合成。

Base-Catalyzed Phenol-Mannich Condensation of Preformed Cesium Iminodiacetate. The Direct Synthesis of Calcein Blue AM and Related Acyloxymethyl Esters.

作者信息

Mikesell Logan D, Livinghouse Tom

机构信息

Department of Chemistry and Biochemistry, Montana State University, Bozeman, Montana 59717, United States.

出版信息

J Org Chem. 2023 Aug 18;88(16):12064-12068. doi: 10.1021/acs.joc.3c00155. Epub 2023 Aug 9.

DOI:10.1021/acs.joc.3c00155

PMID:37556402

Abstract

A rapid and highly practical one-flask procedure for the preparation of (acyloxy)methyl -(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.

摘要

本文描述了一种从亚氨基二乙酸和酚类化合物快速制备（酰氧基）甲基-（2-羟基苄基）亚氨基二乙酸酯及相关二酯的高度实用的单瓶法。这种多组分酚类-曼尼希缩合反应的关键在于使用亚氨基二乙酸铯作为反应底物。该方法已被用于细胞内荧光染料钙黄绿素蓝AM的异常直接合成，目前关于该染料的实验和光谱数据很少。