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Usage

Uses

Used in Chemical Synthesis:
3-(oct-1-yn-1-yl)oxazolidin-2-one is used as a building block for the design of a wide range of chemical transformations. Its strong polarization and reactivity make it a versatile component in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
3-(oct-1-yn-1-yl)oxazolidin-2-one is used as a precursor to highly reactive keteniminium ions, which are valuable intermediates in the synthesis of pharmaceutical compounds. Its use in asymmetric synthesis also contributes to the development of enantioselective reactions, leading to the production of chiral drugs with improved efficacy and reduced side effects.
Used in Catalyst Design:
The reactivity and polarity of 3-(oct-1-yn-1-yl)oxazolidin-2-one make it a promising candidate for the design of novel catalysts. These catalysts can be employed in various chemical reactions, enhancing their efficiency and selectivity, and contributing to the development of greener and more sustainable chemical processes.

Upstream product

• 497-25-6 dimethylenecyclourethane 
• 38761-67-0 1-bromo-1-octyne 
• 629-05-0 n-octyne 
• 54502-24-8 copper(I) hexylacetylenide 
• 762-04-9 phosphonic acid diethyl ester 
• 17176-77-1 Dibenzyl phosphite 
• 1809-20-7 diisopropyl hydrogenphosphonate 
• 108756-88-3 (dicyclohexylphosphino)borane 
• 1013-88-3 Benzophenone imine 

Downstream Products

• 1259391-26-8 3-{1-[1-(2-oxo-oxazolidin-3-yl)meth-(E)-ylidene]heptyl}benzoic acid ethyl ester 

Relevant academic research and scientific papers

Palladium-Catalyzed Silylcyanation of Ynamides: Regio- and Stereoselective Access to Tetrasubstituted 3-Silyl-2-Aminoacrylonitriles

The palladium-catalyzed silylcyanation of ynamides is described. This reaction is fully regioselective, delivering tetrasubstituted 2-aminoacrylonitriles derivatives exclusively. Unexpectedly, the nature (aryl or alkyl) of the substituent located at the β-position of the ynamide directly controls the stereoselectivity. The reaction tolerates a number of functional groups and can be considered as the first general access to fully substituted 2-aminoacrylonitriles. Given the singular reactivity observed, a computational study was performed to shed light on the mechanism of this intriguing transformation. Relying on the specific reactivity of the newly installed vinylsilane functionality, the scope of 2-aminoacrylonitriles has been enlarged by postfunctionalization.

Fishing with copper acetylides: Selective alkynylation of heteronucleophiles

Copper acetylides are readily available and especially convenient reagents for the alkynylation of a broad range of heteronucleophiles. Upon simple activation with molecular oxygen in the presence of suitable ligands and solvents, they readily transfer th

Hydrative Aminoxylation of Ynamides: One Reaction, Two Mechanisms

Organic synthesis boasts a wide array of reactions involving either radical species or ionic intermediates. The combination of radical and polar species, however, has not been explored to a comparable extent. Herein we present the hydrative aminoxylation

Ynamide Preactivation Allows a Regio- and Stereoselective Synthesis of α,β-Disubstituted Enamides

A novel ynamide preactivation strategy enables the use of otherwise incompatible reagents and allows preparation of α,β-disubstituted enamides with high regio- and stereoselectivity. Mechanistic analysis reveals the intermediacy of a triflate-bound intermediate as a solution-stable, effective keteniminium reservoir, whilst still allowing subsequent addition of organometallic reagents.

Enantioselective Construction of Acyclic Quaternary Carbon Stereocenters: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Amide Enolates

We report a divergent and modular protocol for the preparation of acyclic molecular frameworks containing newly created quaternary carbon stereocenters. Central to this approach is a sequence composed of a (1) regioselective and -retentive preparation of allyloxycarbonyl-trapped fully substituted stereodefined amide enolates and of a (2) enantioselective palladium-catalyzed decarboxylative allylic alkylation reaction using a novel bisphosphine ligand.

Efficient and recyclable Cu2(BDC)2(BPY)-catalyzed oxidative amidation of terminal alkynes: Role of bipyridine ligand

We have described an efficient method for oxidative cross coupling reactions between activated N-H amines and terminal alkynes using heterogeneous Cu2(BDC)2(BPY) as recyclable catalyst (BDC = benzene-1,4-dicarboxylate; BPY = 4,4′-bipyridine). The optimal conditions involved the use of inexpensive NaHCO3 base and oxygen as terminal oxidant in toluene solvent at 80°C. Reactions proceeds efficiently, and high selectivity with only trace amount of diynes as well as good yields were achieved in a short reaction time. The Cu2(BDC)2(BPY) exhibited excellent catalytic activity and selectivity as compared to other Cu-MOFs on a broad reaction scope. Interestingly, the presence of bipyridine ligand was shown to enhance the catalyst stability. Thus, the Cu2(BDC)2(BPY) could be facilely separated from the reaction mixture by simple centrifugation and could be reused several times with only a slight decrease in catalytic activity.

Convenient and practical alkynylation of heteronucleophiles with copper acetylides

Copper acetylides, readily available reagents which are characterized by their lack of reactivity, can be simply activated by oxidation with oxygen in the presence of simple nitrogen ligands such as TMEDA or imidazole derivatives. Upon activation, these nucleophilic species undergo a formal umpolung and can transfer their alkyne subunit to a wide range of heteronucleophiles, including amides, oxazolidinones, imines, and dialkyl phosphites. This alkynylation, which provides one of the most practical entry to useful building blocks such as ynamides, ynimines, and alkynylphosphonates, proceeds under especially mild conditions and can be easily performed on a multigram scale. Georg Thieme Verlag Stuttgart, New York.

Heterogeneously catalyzed selective aerobic oxidative cross-coupling of terminal alkynes and amides with simple copper(ii) hydroxide

Simple copper(ii) hydroxide Cu(OH)2 could act as an efficient heterogeneous catalyst for selective oxidative cross-coupling of a broad range of terminal alkynes and amides using air as a sole oxidant, giving the corresponding ynamides in moderate to high yields (56-93% yields). The Royal Society of Chemistry 2012.

A green synthetic route to imides from terminal alkynes and amides by simple solid catalysts

An atom-efficient and green synthetic route to highly valuable imides (5492% yields) from terminal alkynes and amides has been developed. This new route is composed of two consecutive reactions, that is, (i) the reported Cu(OH)2-catalyzed cross-coupling o

Copper-catalyzed alkynylation of amides with potassium alkynyltrifluoroborates: A room-temperature, base-free synthesis of ynamides

(Figure Presented) An efficient copper-mediated method for the coupling of potassium alkynyltrifluoroborates with nitrogen nucleophiles is reported. This reaction provides the first base-free and room-temperature synthesis of ynamides and allows for an easy preparation of these useful building blocks.