![(3R)-4-(4-Chlorophenyl)-3-({[(2-methyl-2-propanyl)oxy]carbonyl}amino)butanoic acid structure](https://static.chemtradehub.com/structs/218/218608-96-9-f871.webp "(3R)-4-(4-Chlorophenyl)-3-({[(2-methyl-2-propanyl)oxy]carbonyl}amino)butanoic acid structure")
(3R)-4-(4-Chlorophenyl)-3-({[(2-methyl-2-propanyl)oxy]carbonyl}amino)butanoic acid
CAS Number:
218608-96-9
Molecular Formula:
C15H20ClNO4
Modular synthesis of oligoacetylacetones via site-selective silylation of acetylacetone derivatives
Literature Information
Publication Date
2020-04-08
DOI
10.1039/D0OB00501K
Impact Factor
3.876
Authors
Parantap Sarkar, Yuya Inaba, Hayato Shirakura, Tomoki Yoneda
View Original
Abstract
Oligoacetylacetones consisting of 3,3-disubstituted pentane-2,4-diones were synthesized through a terminal silylation and oxidative coupling protocol. Highly selective formation of mono-enol silyl ethers of 3,3-disubstituted acetylacetones was achieved using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as a base. Subsequent silver(I) oxide mediated coupling reactions provided tetraketones. Unique substituent dependence was found for the terminal-selective silylation of tetraketones. Finally, octaketones (tetramers of acetylacetone derivatives) with three types of monomer sequences were prepared in their discrete forms. Single crystal X-ray analysis revealed that the solid-state conformations of oligoketone chains were predominantly governed by the ketone sequence rather than substituents. However, differences in the packing structures induced by alkyl substituents led to significant differences in melting points for the structural isomers of octaketones.
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Source Journal
Organic & Biomolecular Chemistry
CiteScore:
3.4
Self-citation Rate:
10.3%
Articles per Year:
1041
Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.
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