59304-44-8

Usage

Explanation

The molecular formula represents the number of atoms of each element present in a molecule. In this case, the compound has 9 carbon (C) atoms, 10 hydrogen (H) atoms, 1 oxygen (O) atom, and 1 sulfur (S) atom.

Explanation

A heterocyclic compound is a cyclic compound that contains atoms of at least two different elements as part of its ring structure. In this case, the thiophene ring contains sulfur in addition to carbon atoms.

Explanation

The thiophene ring is a five-membered ring with four carbon atoms and one sulfur atom. It is a common structural motif in many organic compounds and is known for its aromatic properties.

Explanation

The pent-4-en-1-one group is a five-carbon chain with a double bond between the second and third carbon atoms and a carbonyl group (C=O) at the first carbon atom. This group is attached to the thiophene ring, making the compound a substituted thiophene.

Explanation

1-(thiophen-2-yl)pent-4-en-1-one is used as a building block or intermediate in the synthesis of various organic compounds, including pharmaceuticals and agrochemicals. Its versatile structure allows for the creation of a wide range of products.

Explanation

Studies have shown that 1-(thiophen-2-yl)pent-4-en-1-one may have potential antifungal and antibacterial properties, making it a compound of interest for further research and development in the field of medicine and agriculture.

Explanation

The compound's structure and reactivity make it a valuable intermediate for the synthesis of a wide range of organic compounds. Its ability to participate in various chemical reactions allows for the creation of diverse products with different properties and applications.

Heterocyclic Compound

Yes

Thiophene Ring

Present

Pent-4-en-1-one Group

Present

Application

Organic Synthesis and Pharmaceutical/Agrochemical Preparation

Potential Properties

Antifungal and Antibacterial

Reactivity

Versatile Intermediate

Upstream product

• 591-80-0 pent-4-enoic acid 
• 7103-09-5 4-but-1-enylmagnesium bromide 
• 229970-94-9 N‐methoxy‐N‐methyl‐2‐thiophenecarboxamide 
• 5271-67-0 2-Thiophenecarbonyl chloride 
• 527-72-0 2-thiophenylcarboxylic acid 
• 88-15-3 2-Acetylthiophene 
• 13669-10-8 ethyl 2-thenoylacetate 
• 100117-82-6 2-(thiophene-2-carbonyl)-pent-4-enoic acid ethyl ester 
• 98-03-3 thiophene-2-carbaldehyde 
• 182143-04-0 1-(thiophen-2-yl)pent-4-en-1-ol 
• 5162-44-7 1-bromo-4-butene 

Downstream Products

• 101092-82-4 1-[2]thienyl-pent-4-en-1-one-(2,4-dinitro-phenylhydrazone) 
• 151476-60-7 1-(2-Thienyl)-4-(phenylseleno)-5-azidopentan-1-one 
• 151476-87-8 2-(2-Thienyl)-5-(phenylseleno)-3,4,5,6-tetrahydropyridine 
• 3319-99-1 2'-(2-thienyl)pyridine 

Relevant academic research and scientific papers

Radical-Mediated Distal Ipso-Migration of O/S-Containing Heteroaryls and DFT Studies for Migratory Aptitude

Herein we describe an efficient distal ipso-migration of O- and S-containing heteroaryls and the radical heteroarylation of unactivated alkenes. The migration is triggered by various fluoroalkyl radicals, leading to valuable multifunctionalized ketones. The comparisons of migratory aptitude for O-/S-containing heteroaryls are comprehensively investigated. The origin of the chemoselective migration could be partially attributed to the discrepancy in the energy level of the LUMO of each heteroaryl group.

Highly Enantioselective Construction of Dihydrooxazines via Pd-Catalyzed Asymmetric Carboetherification

A straightforward synthesis of highly enantioenriched 5,6-dihydro-4H-1,2-oxazines is realized by Pd-catalyzed asymmetric carboetherification of γ,δ-alkenyl oximes with (hetero)aryl and alkenyl halides in the presence of a commercially available bisphosphine ligand. The enantioenriched products can be facilely converted to functionalized alcohols with high fidelity of chiral transfer.

An α-Cyclopropanation of Carbonyl Derivatives by Oxidative Umpolung

The reactivity of iodine(III) reagents towards nucleophiles is often associated with umpolung and cationic mechanisms. Herein, we report a general process converting a range of ketone derivatives into α-cyclopropanated ketones by oxidative umpolung. Mechanistic investigation and careful characterization of side products revealed that the reaction follows an unexpected pathway and suggests the intermediacy of non-classical carbocations.

Saturated Bioisosteres of ortho-Substituted Benzenes

Saturated bioisosteres of ortho-disubstituted benzenes (bicyclo[2.1.1]hexanes) were synthesized, characterized and validated. These cores were incorporated into the bioactive compounds Valsartan, Boskalid and Fluxapyroxad instead of the benzene ring. The

Iron-catalyzed carbonylative cyclization of γ,δ-unsaturated aromatic oxime esters to functionalized pyrrolines

Herein, a new method of iron-catalyzed carbonylative cyclization of γ,δ-unsaturated aromatic oxime esters to functionalized pyrrolines has been developed. By using readily available substrates, 32 examples of functionalized pyrrolines were prepared in moderate to good yields. Notably, examples of reduction and cycloaddition reactions of the obtained product were given as well. This journal is

Radical Aza-Cyclization of α-Imino-oxy Acids for Synthesis of Alkene-Containing N-Heterocycles via Dual Cobaloxime and Photoredox Catalysis

Nitrogen-containing heterocycles are prevalent in both naturally and synthetically bioactive molecules. We report herein an unprecedented protocol for radical aza-cyclization of α-imino-oxy acids with pendant alkenes via synergistic photoredox and cobaloxime catalysis. With or without alkenes as the intermolecular cross-coupling partners, the transformation provides a variety of corresponding alkene-containing dihydropyrrole products in satisfactory yields. In the presence of external alkenes, the tandem reaction generates E-selective coupling products with excellent chemo- and stereoselectivity.

Iron-catalyzed acylation-functionalization of unactivated alkenes with aldehydes

Herein, an iron-catalyzed acylation-functionalization of unactivated alkenes with aldehydes via distal group ipso-migration is reported. This strategy overcame the energy barrier and reversibility in the difunctionalization of unactivated alkenes with nuc

Iminyl Radicals by Reductive Cleavage of N-O Bond in Oxime Ether Promoted by SmI2: A Straightforward Synthesis of Five-Membered Cyclic Imines

A new generation method of N-centered radicals from the reductive cleavage of the N-O bond in oxime ether promoted by SmI2 is reported for the first time. The in-situ-generated N-centered radicals underwent intramolecular cyclization to afford five-membered cyclic imines in two manners: N-centered radical addition and N-centered anion nucleophilic substitution. From a synthetic point of view, an efficient synthetic method of five-membered cyclic imines was developed. A mechanism of the transformation was proposed.

Palladium-Catalyzed Hydrocarbonylative Cyclization of 1,5-Dienes

A novel and atom-economic palladium-catalyzed isomerization-hydrocarbonylative cyclization reaction of 1,5-dienes to 2-alkylidenecyclopentanones has been developed, which provides a rapid and straightforward approach to 2-alkylidenecyclopentanones with high stereoselectivity. The reaction was found to proceed via alkene isomerization and selective hydrocarbonylative cyclization to generate 2-alkylidenecyclopentanones with high selectivity.

Oximinotrifluoromethylation of unactivated alkenes under ambient conditions

An efficient protocol for oximinotrifluoromethylation of unactivated alkenes was developed via trifluoromethyl radical-induced intramolecular remote oximino migration under mild reaction conditions, providing a wide range of β-trifluoromethylated oximes. Other fluoroalkyl radicals were also applicable for this transformation. This method provided access to synthetically challenging medium-sized ring scaffolds and the 6,7,5-fused lactam skeleton.