𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Synthesis and fluorescence properties of substituted 7-aminocoumarin-3-carboxylate derivatives

✍ Scribed by John E. T. Corrie; V. Ranjit N. Munasinghe; Wolfgang Rettig

Publisher
Journal of Heterocyclic Chemistry
Year
2000
Tongue
English
Weight
834 KB
Volume
37
Category
Article
ISSN
0022-152X

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

4‐Trifluoromethyl‐ or 6‐bromo‐substituted 7‐diethylaminocoumarin‐3‐carboxamide derivatives 2 and 3, each containing a maleimide have been synthesized as potential fluorescent labeling reagents for thiol groups in proteins and their fluorescence properties have been determined. The 4‐trifluoromethyl substituted compound 2 has a significantly greater Stokes shift than the comparable compound lacking this group, but both the new coumarins have low fluorescence quantum yields (ϕ~f~). When a 4‐trifluoromethyl substituent is present, the 3‐carboxamide is unusually labile to hydrolysis. Bromination of ethyl 7‐diethylaminocoumarin‐3‐carboxylate 17 gave the 6‐ and 8‐bromo derivatives 18 and 19 respectively, and also the 8‐bromo‐7‐monoethylamino compound 20. ϕ~f~ for the latter compound is 100‐fold greater than for its diethylamino analogue 19. Fluorescence lifetime measurements support an interpretation based on the twisted intramolecular charge transfer (TICT) model to explain these large differences in ϕ~f~.

📜 SIMILAR VOLUMES

ChemInform Abstract: Synthesis and Fluor
ChemInform Abstract: Synthesis and Fluorescence Properties of Substituted 7-Aminocoumarin-3-carboxylate Derivatives.
✍ John E. T. Corrie; V. Ranjit N. Munasinghe; Wolfgang Rettig 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 30 KB 👁 2 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v

3-Aminoacetylthiazolidine-4-carboxylate
3-Aminoacetylthiazolidine-4-carboxylate esters and their l-thia-4-azaspiro[4.5]decane-3-carboxylate derivatives. Synthesis and stereochemical properties
✍ N. Pellegrini; B. Refouvelet; J.-C. Rouland; J.-F. Robert; B. Bachet 📂 Article 📅 1997 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 481 KB

## Abstract Dimethyl thiazolidine‐2,4‐dicarboxylate 2 and ethyl l‐thia‐4‐azaspiro[4.5]decane‐3‐carboxylates 3‐5 were obtained as a diastereoisomeric mixture while their 3‐aminoacetyl derivatives were isolated in only one isomeric form. These reactions of __N__‐acylation were stereoselective, which