1,3-dicarbonyl compounds
1,3-Dicarbonyl compounds are a class of organic compounds containing two carbonyl groups (C=O) on adjacent carbon atoms separated by one atom. These compounds play significant roles in various chemical reactions and applications due to their unique structural features. Examples include diacetyl (2,3-pentanedione), which is widely used as a flavoring agent and has been implicated in respiratory issues; and 1,3-butanedione, employed in the synthesis of certain pharmaceuticals and as a reagent in organic chemistry.
Structurally, these compounds can act as both electrophiles and nucleophiles depending on the reaction conditions. They are often intermediates in multistep synthetic sequences due to their ability to undergo various transformations such as aldol condensation, Michael addition, and intramolecular reactions leading to the formation of cyclic structures or new functional groups.
In the industrial sector, 1,3-dicarbonyl compounds find applications in the production of fragrances, food additives, pharmaceuticals, and polymers. Their reactivity makes them versatile precursors for complex organic molecules, contributing to their importance in both academic research and commercial manufacturing processes.
| Structure | Chemical Name | CAS | MF |
|---|---|---|---|
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2-Oxocyclopentanecarboxylic acid | 50882-16-1 | C6H8O3 |
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methyl 3-methyl-2-oxocyclopentane-1-carboxylate | 57964-61-1 | C8H12O3 |
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1,3-Hexanedione,5-methyl-1-(3-methyl-3-cyclohexen-1-yl)- | 72928-14-4 | C14H22O2 |
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9H,9H-Triacontafluoro-8,10-heptadecanedione | 36554-97-9 | C17H2F30O2 |
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2-Pyrrolidinone,3-acetyl- | 31536-38-6 | C6H9NO2 |
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1,1,1,2,2,3,3-Heptafluoroheptane-4,6-dione | 356-30-9 | C7H5F7O2 |
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ethyl 3-bromo-2-oxocyclohexane-1-carboxylate | 30132-23-1 | C9H13BrO3 |
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Propanediamide,2-fluoro- | 815-59-8 | C3H5FN2O2 |
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4-Pyrazolidineaceticacid, 3,5-dioxo- | 876508-60-0 | C5H6N2O4 |
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Ethyl-n-methyl malonamide | 71510-95-7 | C6H11NO3 |
Related Literature
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M. Sheykhan,S. Khani,S. Shaabanzadeh,M. Joafshan Green Chem., 2017,19, 5940-5948
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Michael Kappl,Paul M. Young,Daniela Traini,Sanyog Jain RSC Adv., 2016,6, 25789-25798
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Jieun Kim,Han-Saem Park,Tae-Hee Kim,Sung Yeol Kim,Hyun-Kon Song Phys. Chem. Chem. Phys., 2014,16, 5295-5300
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Chongyang Zhu,Xiaojia Bian,Xin Jia,Ning Tang,Yongqiang Cheng Food Funct., 2020,11, 10635-10644
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José M. Rivera,Mariana Martín-Hidalgo,Jean C. Rivera-Ríos Org. Biomol. Chem., 2012,10, 7562-7565
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