Structure, reactivity, and application of some triketone derivatives

被引：46
作者：
Chen, You-Sheng [1 ]
Kuo, Pei-Yu [1 ]
Shie, Tien-Lan [1 ]
Yang, Ding-Yah [1 ]
机构：
[1] Tunghai Univ, Dept Chem, Taichung 407, Taiwan
来源：
TETRAHEDRON | 2006年 / 62卷 / 40期
关键词：
triketone; polarity-sensitive fluorescent probe; acidichromic colorant;
D O I：
10.1016/j.tet.2006.07.053
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The major tautomer of several triketone derivatives in organic and aqueous solutions has been determined. Their solvent- and base-sensitive properties have been applied in the design of a polarity-sensitive fluorescent probe and an acidichromic colorant, respectively. The regioselective acetylation and methylation of 2-acyldimedone, 3-acyl-4-hydroxycoumarin, and 2-acyl-1,3-indandione have also been investigated. The results indicated that acetylation and methylation of the first two occurred specifically at endocyclic enolic oxygens, whereas for the latter they occurred at exocyclic enolic oxygen. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：9410 / 9416
页数：7
相关论文
共 18 条
[1]  
AKHREM AA, 1979, J ORG CHEM USSR, V15, P2113
[2]  
BOHAC A, 1992, CHEM PAP, V46, P31
[3]   STRUCTURE ELUCIDATION OF ACETYLATION PRODUCTS OF 2-ACYL-1,3-INDANEDIONES BY CORRELATION OF INFRARED SPECTRAL DATA [J].
BOHAC, A ;
PERJESSY, A ;
LOOS, D ;
HRNCIAR, P .
MONATSHEFTE FUR CHEMIE, 1991, 122 (11) :943-948
[4]   INHIBITION OF PLANT ACETYL-COENZYME A CARBOXYLASE BY THE HERBICIDES SETHOXYDIM AND HALOXYFOP [J].
BURTON, JD ;
GRONWALD, JW ;
SOMERS, DA ;
CONNELLY, JA ;
GENGENBACH, BG ;
WYSE, DL .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1987, 148 (03) :1039-1044
[5]  
FOCKE M, 1987, Z NATURFORSCH C, V42, P1361
[6]   Reaction of cyclohexanone benzylimines with ethylidenemalonate diesters.: Diphenyl 2-ethylidenemalonate:: A highly electrophilic synthetic equivalent of crotonic esters [J].
Jabin, I ;
Revial, G ;
Monnier-Benoit, N ;
Netchitaïlo, P .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (01) :256-261
[7]   Interaction of (4-hydroxyphenyl)pyruvate dioxygenase with the specific inhibitor 2-[2-nitro-4-(trifluoromethyl)benzoyl]-1,3-cyclohexanedione [J].
Kavana, M ;
Moran, GR .
BIOCHEMISTRY, 2003, 42 (34) :10238-10245
[8]   SYNTHESES OF FLUORESCENT DYES .9. NEW 4-HYDROXYCOUMARINS, 4-HYDROXY-2-QUINOLONES, 2H,5H-PYRANO[3,2-C]BENZOPYRAN-2,5-DIONES AND 2H,5H-PYRANO[3,2-C]QUINOLINE-2,5-DIONES [J].
KNIERZINGER, A ;
WOLFBEIS, OS .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1980, 17 (02) :225-229
[9]   STRUCTURES OF 2 2-ACYL-1,3-INDANDIONES [J].
KORP, JD ;
BERNAL, I ;
LEMKE, TL .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1980, 36 (FEB) :428-434
[10]   Synthesis of novel triketone-based acidichromic colorants [J].
Lin, CT ;
Shih, JH ;
Chen, CL ;
Yang, DY .
TETRAHEDRON LETTERS, 2005, 46 (30) :5033-5037
12