28435-47-4

Upstream product

• 538-44-3 (E)-benzylidenepinacolone 
• 17474-12-3 4,4-dimethyl-1-phenyl-pent-2-yn-1-ol 
• 866562-21-2 4,4-dimethyl-1-phenylpent-2-ynyl acetate 
• 917-92-0 3,3-Dimethylbut-1-yne 
• 100-52-7 benzaldehyde 
• 1486-28-8 diphenyl(methyl)phosphine 
• 5469-26-1 1-Bromopinacolon 
• 32398-67-7 4,4-dimethyl-1-phenyl-1-pentyn-3-one 
• 75-97-8 3,3-dimethyl-butan-2-one 
• 68970-19-4 bis(3,3-dimethyl-2-oxobutyl)tellurium dichloride 
• 329-98-6 phenylmethylsulphonyl fluoride 
• 102-92-1 Cinnamoyl chloride 
• 132350-97-1 4,4-dimethyl-1-phenyl-pent-1-yn-3-ol 
• 64788-85-8 dimethyl-phenyl-((E)-styryl)-silane 

Downstream Products

• 55830-01-8 (Z)-3,4,4-Trimethyl-1-phenyl-pent-1-en-3-ol 
• 538-44-3 (E)-benzylidenepinacolone 
• 5195-24-4 4,4-dimethyl-1-phenylpentan-3-one 
• 31611-82-2 (1RS,2SR)-1,2-dibromo-4,4-dimethyl-1-phenyl-pentan-3-one 
• 101115-14-4 2,2-dimethyl-6-nitro-5-phenylhexane-3-one 
• 55830-03-0 2,2-dimethyl-5-phenylhexan-3-one 
• 55830-02-9 1,2-adduct from 7 
• 56068-54-3 2,2-Dimethyl-5,6,6,6-tetraphenyl-hexan-3-one 
• 69370-39-4 2,6,6-Trimethyl-5-oxo-3-phenylheptansaeure 
• 69370-40-7 2-Ethyl-6,6-dimethyl-5-oxo-3-phenylheptansaeure 
• 69370-41-8 2-Isopropyl-6,6-dimethyl-5-oxo-3-phenylheptansaeure 
• 69370-42-9 2-tert-Butyl-6,6-dimethyl-5-oxo-3-phenylheptansaeure 
• 97060-88-3 (E,3RS,1'RS)-3-(1'-tert-butyl-1'-hydroxy-3'-phenyl-2'-propenyl)-1-methyl-2-pyrrolidone 
• 122969-27-1 (3RS,1'RS)-3-(4',4'-dimethyl-3'-oxo-1'-phenylpentyl)-1-methyl-2-pyrrolidinone 

Relevant academic research and scientific papers

Mechanochemical Syntheses of N-Containing Heterocycles with TosMIC

A mechanochemical van Leusen pyrrole synthesis with a base leads to 3,4-disubstitued pyrroles in moderate to excellent yields. The developed protocol is compatible with a range of electron-withdrawing groups and can also be applied to the synthesis of oxazoles. Attempts to mechanochemically convert the resulting pyrroles into porphyrins proved to be difficult.

Borane-Catalyzed, Chemoselective Reduction and Hydrofunctionalization of Enones Enabled by B-O Transborylation

The use of stoichiometric organoborane reductants in organic synthesis is well established. Here these reagents have been rendered catalytic through an isodesmic B-O/B-H transborylation applied in the borane-catalyzed, chemoselective alkene reduction and formal hydrofunctionalization of enones. The reaction was found to proceed by a 1,4-hydroboration of the enone and B-O/B-H transborylation with HBpin, enabling catalyst turnover. Single-turnover and isotopic labeling experiments supported the proposed mechanism of catalysis with 1,4-hydroboration and B-O/B-H transborylation as key steps.

Chemoselective reduction of ?,￠-unsaturated carbonyl and carboxylic compounds by hydrogen iodide

The selective reduction of ?,￠-unsaturated carbonyl compounds was achieved to produce saturated carbonyl compounds with aqueous HI solution. The introduction of an aryl group at an ? or ￠ position efficiently facilitated the reduction with good yield. The reaction was applicable to compounds bearing carboxylic acids and halogen atoms. Through the investigation of the reaction mechanism, it was found that Michael-type addition of iodide occurred to produce ￠-iodo compounds followed by the reduction of C-I bond via anionic and radical paths.

Discovery of trisubstituted pyrazolines as a novel scaffold for the development of selective phosphodiesterase 5 inhibitors

Celecoxib, is a selective cyclooxygenase-2 (COX2) inhibitor with a 1,5-diaryl pyrazole scaffold. Celecoxib has a better safety profile compared to other COX2 inhibitors having side effects of systemic hypertension and thromboembolic complications. This may be partly attributed to an off-target activity involving phosphodiesterase 5 (PDE5) inhibition and the potentiation of NO/cGMP signalling allowing coronary vasodilation and aortic relaxation. Inspired by the structure of celecoxib, we synthesized a chemically diverse series of compounds containing a 1,3,5-trisubstituted pyrazoline scaffold to improve PDE5 inhibitory potency, while eliminating COX2 inhibitory activity. SAR studies for PDE5 inhibition revealed an essential role for a carboxylic acid functionality at the 1-phenyl and the importance of the non-planar pyrazoline core over the planar pyrazole with the 5-phenyl moiety tolerating a range of substituents. These modifications led to new PDE5 inhibitors with approximately 20-fold improved potency to inhibit PDE5 and no COX-2 inhibitory activity compared with celecoxib. PDE isozyme profiling of compound 11 revealed a favorable selectivity profile. These results suggest that trisubstituted pyrazolines provide a promising scaffold for further chemical optimization to identify novel PDE5 inhibitors with potential for less side effects compared with available PDE5 inhibitors used for the treatment of penile erectile dysfunction and pulmonary hypertension.

Asymmetric transfer hydrogenation of cycloalkyl vinyl ketones to allylic alcohols catalyzed by ruthenium amido complexes

A chemoselective 1,2-reduction of cycloalkyl vinyl ketones via asymmetric transfer hydrogenation is described. The reduction proceeded smoothly with a chiral diamine ruthenium complex as a catalyst and a HCOOH-NEt3 azeotrope as both a hydrogen source and solvent under mild conditions. A wide range of 1-cycloalkyl chiral allylic alcohols were obtained in good yields and up to 87% ee. It was found that the alkyl group plays an important role in the enantioselectivity.

Allyl-Nickel Catalysis Enables Carbonyl Dehydrogenation and Oxidative Cycloalkenylation of Ketones

We herein disclose the first report of a first-row transition metal-catalyzed α,β-dehydrogenation of carbonyl compounds using allyl-nickel catalysis. This development overcomes several limitations of previously reported allyl-palladium-catalyzed oxidation, and is further leveraged for the development of an oxidative cycloalkenylation reaction that provides access to bicycloalkenones with fused, bridged, and spirocyclic ring systems using unactivated ketone and alkene precursors.

Visible Light-Induced Aerobic Epoxidation of α,β-Unsaturated Ketones Mediated by Amidines

An aerobic photoepoxidation of α,β-unsaturated ketones driven by visible light in the presence of tetramethylguanidine (3b), tetraphenylporphine (H2TPP), and molecular oxygen under mild conditions was revealed. The corresponding α,β-epoxy ketones were obtained in yields of up to 94% in 96 h. The reaction time was shortened to 4.6 h by flow synthesis. The mechanism related to singlet oxygen was supported by experiments and density functional theory (DFT) calculations.

Chalcone and cinnamate synthesis via one-pot enol silane formation-Mukaiyama aldol reactions of ketones and acetate esters

Aryl alkyl ketones, acetate esters, and acetamides undergo facile one-pot enol silane formation, Mukaiyama aldol addition, and dehydrosilyloxylation in the presence of an amine base and excess trimethylsilyl trifluoromethanesulfonate. The chalcone and cinnamate products are generally recovered in high yield. The relative stoichiometry of the trimethylsilyl trifluoromethanesulfonate and amine base reagents determines whether the reaction yields the β-silyloxy carbonyl product or the α,β-unsaturated carbonyl.

Stereospecific Decarboxylative Nazarov Cyclization Mediated by Carbon Dioxide for the Preparation of Highly Substituted 2-Cyclopentenones

Highly substituted 2-cyclopentenones were stereospecifically and regioselectively constructed with high catalytic efficiency through Lewis-acid catalyzed decarboxylative Nazarov cyclization of the cyclic carbonate derivative, which is prepared by reacting the propargyl alcohol with carbon dioxide in the presence of a silver catalyst. The stereochemistry of the 2-cyclopentenone is strictly controlled by the geometry of the alkene in the starting material. This method is applicable for various substrates.