30780-30-4

Upstream product

• 590-90-9 1-Hydroxy-3-butanone 
• 121-69-7 N,N-dimethyl-aniline 
• 5432-53-1 4-p-dimethylaminophenyl-3-buten-2-one 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 78-94-4 methyl vinyl ketone 
• 598-32-3 2-hydroxy-3-butene 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 29546-14-3 4-((1H-benzo[d][1,2,3]triazol-1-yl)methyl)-N,N-dimethylaniline 
• 123-54-6 acetylacetone 

Downstream Products

• 81580-13-4 5-{2-[3-(4-Dimethylamino-phenyl)-1-methyl-propylamino]-1-hydroxy-ethyl}-2-hydroxy-benzamide 
• 13026-64-7 <3-(4-Dimetylamino-phenyl)-1-methyl-propyl>-<3,3-diphenylpropyl>-amin 

Relevant academic research and scientific papers

Gold-catalyzed hydroarylation of alkenes with dialkylanilines

Anti-Bredt di(amino)carbene supported gold(I) chloride complexes are readily prepared in two steps from the corresponding isocyanide complexes. In the presence of KB(C6F5)4as chloride scavenger, they promote the unprecedented hydroarylation reaction of alkenes with N,N-dialkylanilines with high para-selectivity. The latter are challenging arenes for Friedel-Craft reactions, due to their high basicity.

Boron-Catalyzed Dehydrative Friedel-Crafts Alkylation of Arenes Using β-Hydroxyl Ketone as MVK Precursor

Boron-catalyzed environmentally benign dehydrative Friedel-Crafts alkylation of indole/pyrrole and aniline derivatives with β-hydroxyl ketones has been developed for the first time. This method provides an efficient and green replacement of toxic and unst

Michael Additions Catalyzed by a β-Diketiminate-Supported Aluminum Complex

A β-diketiminate-supported aluminum bistriflate complex (DipLAl(OTf)2·Na[BArCl4]; DipL = CH(CMe)2(N-C6H3-iPr2)2; Tf = O2SCF

B(C6F5)3-Catalyzed Michael Reactions: Aromatic C-H as Nucleophiles

The Michael reaction is a widely used reaction for the C-C coupling of electron-poor olefins and C(sp3)-H pronucleophiles. Herein we report the Michael reaction between alkenes and aromatic as well as heteroaromatic compounds as aromatic C(sps

A Hantzsch Amido Dihydropyridine as a Transfer Hydrogenation Reagent for α,β-Unsaturated Ketones

An improved synthesis of the bis-methylamido Hantzsch dihydropyridine is described. The Hantzsch amide is demonstrated to be an effective transfer hydrogenation reagent using α,β-unsaturated ketones as the test case. Unreacted Hantzsch amide and the bis-methylamidopyridine byproduct are effectively removed by extraction in contrast to the commonly used Hantzsch diethyl ester. Several examples are given with the reaction being more effective for conjugated aromatic substrates than for aliphatics.

Controlling olefin isomerization in the heck reaction with neopentyl phosphine ligands

The use of neopentyl phosphine ligands was examined in the coupling of aryl bromides with alkenes. Di-tert-butylneopentylphosphine (DTBNpP) was found to promote Heck couplings with aryl bromides at ambient temperature. In the Heck coupling of cyclic alkenes, the degree of alkene isomerization was found to be controlled by the choice of ligand with DTBNpP promoting isomerization to a much greater extent than trineopentylphosphine (TNpP). Under optimal conditions, DTBNpP provides high selectivity for 2-aryl-2,3-dihydrofuran in the arylation of 2,3-dihydrofuran, whereas TNpP provided high selectivity for the isomeric 2-aryl-2,5-dihydrofuran. A similar complementary product selectivity is seen in the Heck coupling of cyclopentene. Heck coupling of 2-bromophenols or 2-bromoanilides with 2,3-dihydrofurans affords 2,5-epoxybenzoxepin and 2,5-epoxybenzazepins, respectively.

Novel diarylheptanoids as inhibitors of TNF-α production

Synthesis and anti-inflammatory activity of novel diarylheptanoids [5-hydroxy-1-phenyl-7-(pyridin-3-yl)-heptan-3-ones and 1-phenyl-7-(pyridin-3-yl) hept-4-en-3-ones] as inhibitors of tumor necrosis factor-α (TNF-α) production is described in the present article. The key reactions involve the formation of a β-hydroxyketone by the reaction of substituted 4-phenyl butan-2-ones with pyridine-3-carboxaldehyde in presence of LDA and the subsequent dehydration of the same to obtain the α,β-unsaturated ketones. Compounds 4i, 5b, 5d, and 5g significantly inhibit lipopolysaccharide (LPS)-induced TNF-α production from human peripheral blood mononuclear cells in a dose-dependent manner. Of note, the in vitro TNF-α inhibition potential of 5b and 5d is comparable to that of curcumin (a naturally occurring diarylheptanoid). Most importantly, oral administration of 4i, 5b, 5d, and 5g (each at 100 mg/kg) but not curcumin (at 100 mg/kg) significantly inhibits LPS-induced TNF-α production in BALB/c mice. Collectively, our findings indicate that these compounds may have potential therapeutic implications for TNF-α-mediated auto-immune/inflammatory disorders.

Ionic hydrogenation of α,β-unsaturated ketones with cyclohexane in the presence of aluminum halides

4-Methyl-3-penten-2-one, 3-hepten-2-one, 3-methyl-1-phenyl-2-buten-1-one, 4-(2,4-dichlorophenyl)-, 4-(4-hydroxyphenyl)-, 4-(4-methoxyphenyl)-, 4-(2-hydroxyphenyl)-, and 4-(4-dimethylaminophenyl)-3-buten-2-ones, and 3-(4-methoxyphenyl)-1-phenyl-2-propenone react with cyclohexane in the presence of excess aluminum chloride or aluminum bromide in CH2Cl2 or CH2Br2, respectively, at room temperature to form the corresponding saturated ketones in high yields. Using 4-phenyl-and 4-(4-methoxyphenyl)-3-buten-2-ones as examples, it was shown that the reaction pattern does not change in going from the Lewis acids AlCl3, and AlBr3 to proton-donor acid system CF3SO3H-SbF5. The reactive intermediates are likely to be C-protonated complexes of α,β-unsaturated ketones with aluminum halides or their O,C-diprotonated analogs.

Effect of charge distribution on selective hydrogenation of conjugated enones catalyzed by iridium complexes

Chemoselectivity in the reduction of substituted conjugated enones catalyzed by iridium/phosphine systems appears to be slightly dependent on the charge distribution around the carbonyl group of the substrates: electron, withdrawing groups enhance the reduction rate of the ketonic function. Enantioselectivity, in the case of the catalytic system studied, appears to be related essentially to the steric hindrance in the substrate.

Benzotriazole as a Synthetic Auxiliary: Advantageous Syntheses of Substituted Diarylmethanes and Heterocyclic Analogues

4-(Benzotriazol-1-ylmethyl)-N,N-dimethylaniline (1b) can be substituted at the CH2 link via lithiation.Both the parent and substituted derivatives react with a variety of electron-rich benzenoid and heteroaromatic compounds in a novel approach to leuco dy