Investigations on the synthesis and chemiluminescence of novel 2-coumaranones - II

被引：19

作者：

Schramm, Stefan ^{[1
]}

Monteiro Leite Ciscato, Luiz Francisco ^{[2
]}

Oesau, Pascal ^{[1
]}

Krieg, Reimar ^{[3
]}

Richter, Jan Frank ^{[3
]}

Navizet, Isabelle ^{[4
]}

Roca-Sanjuan, Daniel ^{[5
]}

Weiss, Dieter ^{[1
]}

Beckert, Rainer ^{[1
]}

机构：

[1] Univ Jena, Inst Organ Chem & Makromol Chem, Humboldtstr 10, D-07743 Jena, Germany

[2] Univ Fed ABC, Ctr Ciencias Nat & Humanas, BR-09210170 Santo Andre, SP, Brazil

[3] Univ Klinikum Jena, Inst Anat 2, D-07743 Jena, Germany

[4] Univ Paris Est, Lab Modelisat & Simulat Multi Echelle, MSME UMR 8208, CNRS, F-77454 Marne La Vallee, France

[5] Uppsala Univ, Dept Chem Angstrom, Theoret Chem Programme, S-75002 Uppsala, Sweden

来源：

ARKIVOC | 2015年

基金：

巴西圣保罗研究基金会;

关键词：

2-Coumaranone; chemiluminescence; chemiexcitation; 1,2-dioxetanones; alpha-peroxylactones; CIEEL; firefly bioluminescence; ACYL-ALPHA-ARYLGLYCINES; INTERMEDIATE;

D O I：

10.3998/ark.5550190.p009.044

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The optimized one-pot synthesis of 16 new 2-coumaranones containing a carbamate side-chain is described. Furthermore, the quantum yields for the base-activated chemiluminescence in the presence of oxygen was determined for all compounds, with a maximum of 5.9 +/- 0.1 x 10(-2) E mol(-1), and the application of these compounds as substitutes for usual bioluminescent and chemiluminescent reagents in bioassays is anticipated. A preliminary mechanistic pathway is also suggested, making use of recent developments regarding aspects of organic chemiluminescence, in agreement with both experimental and theoretical data available on the induced 1,2-dioxetanone decomposition as well as with the high efficiency of this reaction.

引用

页码：44 / 59

页数：16

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