81187-86-2

Upstream product

• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 99-91-2 para-chloroacetophenone 
• 21133-98-2 ethyl 3-(4-chlorophenyl)-3-hydroxybutanoate 
• 1195-42-2 N-cyclohexylisopropylamine 
• 57025-65-7 2-(trimethylsilyl)butanoic acid 
• 32400-20-7 lithium cyclohexylisopropylamide 
• 104-88-1 4-chlorobenzaldehyde 
• 1712-70-5 1-chloro-4-(1-methylethenyl)-benzene 
• 4755-77-5 Ethyl oxalyl chloride 
• 97025-43-9 ethyl 3-(toluene-4-sulfonyloxy)but-2-enoate 
• 1679-18-1 4-Chlorophenylboronic acid 
• 1474-78-8 triethyl phosphonoformate 
• 106-39-8 bromochlorobenzene 
• 623-70-1 ethyl (E)-crotonate 

Downstream Products

• 106201-12-1 methyl 3-(4-chlorophenyl)-2-butenoate 
• 21758-07-6 3-(4-chloro-phenyl)-crotonic acid 
• 114566-93-7 ethyl 4-bromo-3-(4-chlorophenyl)-2-butenoate 
• 26717-53-3 4-(4-chlorophenyl)furan-2(5H)-one 
• 1309583-78-5 (E)-3-(4-chlorophenyl)-1-phenyl-2-buten-1-one 
• 93404-36-5 (2E)-3-(4'-chlorophenyl)but-2-en-1-ol 
• 1134201-72-1 (-)-(R)-3-(4-methoxyphenyl)butan-1-ol 
• 894421-57-9 (Z)-ethyl 4-azido-3-(4-chlorophenyl)but-2-enoate 
• 63701-55-3 (R)-(-)-baclofen hydrochloride 
• 123632-31-5 (S)-(+)-4-(4-chlorophenyl)pyrrolidin-2-one 
• 123632-35-9 (R)-(-)-4-(4-chlorophenyl)pyrrolidin-2-one 
• 1326755-40-1 C₁₂H₁₅ClO₂ 
• 1446100-81-7 3-(4-chlorophenyl)-3-methylindan-1-one 
• 1446100-82-8 3-(4-chlorophenyl)-3,6-dimethylindan-1-one 

Relevant academic research and scientific papers

Palladium-Catalyzed Allyl-Allyl Reductive Coupling of Allylamines or Allylic Alcohols with H2as Sole Reductant

Catalytic carbon-carbon bond formation building on reductive coupling is a powerful method for the preparation of organic compounds. The identification of environmentally benign reductants is key for establishing an efficient reductive coupling reaction. Herein an efficient strategy enabling H2 as the sole reductant for the palladium-catalyzed allyl-allyl reductive coupling reaction is described. A wide range of allylamines and allylic alcohols as well as allylic ethers proceed smoothly to deliver the C-C coupling products under 1 atm of H2. Kinetic studies suggested that the dinuclear palladium species was involved in the catalytic cycle.

Cobalt-Catalyzed Diastereo- And Enantioselective Reductive Allyl Additions to Aldehydes with Allylic Alcohol Derivatives via Allyl Radical Intermediates

Catalytic generation of ambiphilic π-allyl-metal complexes and their utility in enantioselective transformations constitutes a powerful approach for introduction of allyl groups to a molecule. Herein an unprecedented cobalt-catalyzed highly site-, diastereo-, and enantioselective protocol for stereoselective formation of nucleophilic allyl-Co(II) complexes followed by addition to aldehydes is presented. The reaction features diastereo- and enantioconvergent conversion of easily accessible allylic alcohol derivatives to diversified enantioenriched homoallylic alcohols with a remarkably broad scope of allyl groups that can be introduced. Mechanistic studies indicated that allyl radical intermediates were involved in this process. These new discoveries establish a new strategy for development of enantioselective transformations through capture of radicals by chiral Co complexes, pushing forward the frontier of Co complexes for enantioselective catalysis.

Metal-Free Hydropyridylation of Thioester-Activated Alkenes via Electroreductive Radical Coupling

An electrochemical hydropyridylation of thioester-activated alkenes with 4-cyanopyridines has been developed. The reactions experience a tandem electroreduction of both substrates on the cathode surface, protonation, and radical cross-coupling process, resulting in a variety of valuable pyridine variants, which contain a tertiary and even a quaternary carbon at the α-position of pyridines, in high yields. The employment of thioesters to the conjugated alkenes enables no requirement of catalyst and high temperature, representing a highly sustainable synthetic method.

Synthesis method of beta-chloro acid ester and alpha, beta-unsaturated acid ester compound

The invention belongs to the technical field of organic chemistry, and particularly relates to a synthesis method of beta-chloro acid ester and an alpha, beta-unsaturated acid ester compound. The structure of the compound is characterized by 1H NMR and 13C NMR and is confirmed. The method comprises the steps of by taking acetonitrile as a solvent, carrying out fragmentation on olefin, chlorooxalic acid monoester and 2, 6-dimethyl pyridine under a photocatalytic condition to generate an alkoxyacyl free radical intermediate, carrying out free radical addition reaction on the alkoxyacyl free radical intermediate and the olefin to generate carbon free radicals, then carrying out chlorination reaction to obtain the beta-chloro acid ester compound, and carrying out dehydrochlorination reaction under a DBU condition to generate the alpha, beta-unsaturated acid ester compound. The preparation method of the compound disclosed by the invention has the advantages of starting from olefin, being mild in condition, simple and efficient, strong in functional group compatibility and wide in substrate application range, and various beta-chloro acid ester and alpha, beta-unsaturated acid ester compounds can be synthesized from highly commercialized raw materials. On the basis of photoreaction of fluid chemistry, a target product can also be obtained with a relatively good yield, and the method has very good industrial and medicinal chemistry application values.

Cobalt-Catalyzed Asymmetric 1,4-Hydroboration of Enones with HBpin

Herein, a series of new 8-OIQ cobalt complexes were synthesized and used for cobalt-catalyzed chemo- and enantioselective 1,4-hydroboration of enones with HBpin to access chiral β,β-disubstituted ketones with good to excellent chemo- and enantioselectivties. This protocol is operationally simple and shows a broad substrate scope.

Catalytic Asymmetric Transfer Hydrogenation of trans-Chalcone Derivatives Using BINOL-derived Boro-phosphates

Chiral phosphoric-acid-catalyzed asymmetric reductions of trans-chalcones have been investigated in this work. A BINOL-derived boro-phosphate-catalyzed asymmetric transfer hydrogenation of the carbon-carbon double bond of trans-chalcone derivatives employing borane as a hydride source was realized. This methodology provides a convenient procedure to access chiral dihydrochalone derivatives in high yields and with high enantioselectivities under mild conditions.

NHC-catalyzed asymmetric α-regioselective [4 + 2] annulation to construct α-alkylidene-δ-lactones

The unprecedented NHC-catalyzed [4 + 2] annulation of α-bromoenals with dioxopyrrolidines is described. This protocol features broad substrate scope and allows rapid assembly of α-alkylidene-δ-lactones in good to high yields with excellent enantioselectivities. Notably, this process includes α-regioselective activation of azolium dienolate intermediates, which has not yet been reported.

Synergistic N-Heterocyclic Carbene/Palladium-Catalyzed [3 + 2] Annulation of Vinyl Enolates with 1-Tosyl-2-vinylaziridine

The synergistic combination of N-heterocyclic carbene organocatalysis and transition-metal catalysis for a formal [3 + 2] annulation between 3-substituted but-2-enoates and 1-tosyl-2-vinylaziridine was developed. This cooperative strategy provides a facile and efficient access to various functionalized (E)-3-ethylidene-4-vinylpyrrolidin-2-ones in a regioselective and stereoselective manner. The preliminary asymmetric studies were also performed, which indicated a potential for enantioselective annulation of vinyl enolate intermediates with transition-metal-π-allyl species.

Dihydropyrrolones as bacterial quorum sensing inhibitors

Bacteria regulate their pathogenicity and biofilm formation through quorum sensing (QS), which is an intercellular communication system mediated by the binding of signaling molecules to QS receptors such as LasR. In this study, a range of dihydropyrrolone (DHP) analogues were synthesized via the lactone-lactam conversion of lactone intermediates. The synthesized compounds were tested for their ability to inhibit QS, biofilm formation and bacterial growth of Pseudomonas aeruginosa. The compounds were also docked into a LasR crystal structure to rationalize the observed structure-activity relationships. The most active compound identified in this study was compound 9i, which showed 63.1% QS inhibition of at 31.25 μM and 60% biofilm reduction at 250 μM with only moderate toxicity towards bacterial cell growth.

Nickel-Catalyzed Chemoselective Asymmetric Hydrogenation of α,β -Unsaturated Ketoimines: An Efficient Approach to Chiral Allylic Amines

An efficient synthetic route to chiral allylic amines has been developed by nickel/(S,S)-Ph-BPE complex catalyzed chemoselective asymmetric hydrogenation of α,β-unsaturated ketoimines. Varieties of α,β-unsaturated ketoimines have been well tolerated in this transformation to give chiral allylic amines with high yields and excellent ee values (up to 99% yield, up to 99% ee). A gram-scale reaction with 0.2 mol % catalyst loading has also been achieved.