25540-73-2

Upstream product

• 941-98-0 1'-naphthacetophenone 
• 630-18-2 tert-butyl isocyanide 
• 90-11-9 1-Bromonaphthalene 
• 3282-30-2 pivaloyl chloride 
• 79722-74-0 2-<<2,2-dimethyl-1-(1-naphthyl)propylidene>amino>-2,4,4-trimethylpentane 
• 703-55-9 1-naphthylmagnesiumbromide 
• 91-20-3 naphthalene 
• 74-88-4 methyl iodide 
• 61838-78-6 2-methyl-1-(1-naphthalenyl)-1-propanone 
• 71-43-2 benzene 
• 594-19-4 tert.-butyl lithium 
• 879-18-5 naphthalene-1-carbonic acid chloride 

Downstream Products

• 91-20-3 naphthalene 
• 754-10-9 2,2-dimethylpropionamide 

Relevant academic research and scientific papers

Configurational and conformational NMR study of enantiopure 2,2-dimethyl-1-(1-naphthyl)propanol via its carbamate derivatives

2,2-Dimethyl-1-(1-naphthyl)propanol was synthesized and the corresponding enantiomers were isolated by chiral HPLC. These enantiomers gave diastereoisomeric carbamates by reaction with (S)-(-)-1-phenylethylisocyanate, which were studied by NMR. The comparison of NMR data and molecular mechanics calculations allowed us to determine the absolute configuration of corresponding alcohols. Finally, x-ray results were in agreement with the absolute configuration proposed from the NMR spectra. Copyright

Copper-catalyzed remote C–H arylation of polycyclic aromatic hydrocarbons (PAHs)

The regioselective C–H arylation of substituted polycyclic aromatic hydrocarbons (PAHs) is a desired but challenging task. A copper-catalyzed C7–H arylation of 1-naphthamides has been developed by using aryliodonium salts as arylating reagents. This protocol does not need to use precious metal catalysts and tolerates wide variety of functional groups. Under standard conditions, the remote C–H arylation of other PAHs including phenanthrene-9-carboxamide, pyrene-1-carboxamide and fluoranthene-3carboxamide has also accomplished, which provides an opportunity for the development of diverse organic optoelectronic materials.

Chiral phosphoric acid catalyzed asymmetric transfer hydrogenation of bulky aryl ketones with ammonia borane

An asymmetric transfer hydrogenation of bulky aryl ketones with ammonia borane was successfully realized with chiral phosphoric acid (CPA) as catalyst and water as additive. A variety of optically active secondary alcohols were obtained in good to high yi

Ultrasound assisted Friedel-Crafts acylation of aromatics using ferric sulphate as catalyst

The use of ultrasound in the acylation reactions of various aromatics and polyaromatics with different acyl chlorides, in the presence of catalytic amount of ferric sulphate at room temperature, gives good yields of the respective ketones with a short reaction time. A facile and simple synthesis of various aromatic ketones using Friedel-Crafts acylation has been established from the corresponding acid chlorides and aromatic or polyaromatic compounds, respectively under mild reaction conditions with shorter reaction times (30-45 min) and in reasonable yields. This method offers the advantage of low cost and ease of purification of the products because of the small amount of ferric sulphate used in these reactions.

Phase-transfer alkylation of α-acetylnaphthalene

Reactions of 1-acetylnaphthalene with alkyl iodides in a two-phase system solid-liquid (benzene-solid potassium hydroxide) in the presence of 18-crown-6 as phase-transfer catalyst at room temperature yield mainly the corresponding 1-naphthyl dialkylmethyl ketones (41-78%). The regioselectivity of C-alkylation decreases with increasing length of the hydrocarbon chain in alkyl iodide. Alkylation of isopropyl 1-naphthyl ketone at elevated temperature results in formation of tert-butyl 1-naphthyl ketone.

A facile synthesis of pivalophenones by ultrasound assisted AlCl3 catalysed Friedel-Crafts reaction

Pivalophenones have been prepared by the acylation reaction of various aromatic and heterocyclic compounds with pivaloyl chloride using AlCl3 as catalyst under sonochemical conditions in a short reaction time and in reasonable yields.

Facile synthesis of pivalophenones by an ultrasound assisted iodine catalysed Friedel-Crafts acylation reaction

The use of ultrasound in the acylation reactions of various aromatics and heterocyclics with pivaloyl chloride in the presence of catalytic amount of iodine, without any added solvent and at room temperature, gives excellent yields of the respective pivalophenones in a short reaction time.

The Nitration of α- and β-Acylnaphthalenes

The nitration of α- and β-acylnaphthalenes with copper(II) nitrate in acetic anhydride or nitric acid/acetic acid mixtures gives high yields of the corresponding mononitro compounds.The assignment of constitution to these products is made on the basis of extensive 1H n.m.r. chemical shift and coupling constant data.In the case of α-acylnaphthalenes, with the notable exception of α-pivalonaphthone, nitration occurs in the α-positions of the unsubstituted ring to give mixtures of 5- and 8-nitro compounds. α-Pivalonaphthone gives appreciable amounts of the 4-nitro compound and also of the 8-nitro compound.This result indicates that the pivaloyl group does not shield the 8-position sterically to any significant extent and is effectively electronically neutral, unlike the other acyl substituents, in allowing attack at the α-position (position 4) of the acylated ring.This result is ascribable to the lack of coplanarity of the pivaloyl group with the naphthalene system.All of the β-acylnaphthalenes gave mixtures of 4-, 5- and 8-nitro derivatives in proportions that did not vary significantly with the nature of the acyl group.

Synthesis of potential inhibitors of squalenepoxidase with conformationanl fixation of the structural elements of Butenafine

The synthesis of the naphthalinemethanamines 6b-h is reported. To obtain products with conformative rigidity, substituents with gradually increased space demand were placed into the α-position. Since the direct reductive amination of the naphthylalkanones 3 with the amines 9 or 10 was only of very limited use the α-substituted naphthalinmethanamines 2 and 4 were synthesized as useful intermediates by various methods and the desired N-substitution pattern of the target compounds was subsequently built up applying - mostly reductive - alkylation methods.

Application of Force Field Calculations, 7. - Synthesis and Thermolysis of 1,1'-Disubstitueted trans-Azoneopentanes. - Steric and Resonance Effects of the Substituents on the Thermal Stability of Secondary Azoalkanes

A number of secondary azoalkanes 1, R1R2CH-N=N-CHR1R2, R1 = t-C4H9, R2 = aryl (meso- and D,L-1a-i) and R2 = cyclo-C6H11 (D,L-1k), have been synthesized by partial catalytic hydrogenation of the corresponding ketazines.The configuration of 1 was elucidated by photolysis of crystalline samples of 1, which yielded the dimers 6 with retention of configuration.The kinetics of thermal fragmentation of 1a-k and of 1n (R1 = CH3, R2 = C6H5) into the radicals 7 was followed by DSC.The activation parameters were determined by fitting theoretical curves to the experimental data with the help of a computer program. - The rate of decomposition of 1 with R1, R2 = alkyl is sterically accelarated by increasing size of the substituents (back strain), but the fragmentation of 1a-i (R2 = aryl) is sterically inhibited, e.g. k 2 = C6H5, R1 = t-C4H9)>/k 2 = C6H5, R1 = CH3)> = 10-2.The strain enthalpies Hs of 1 and 7 were calculated by the force field method.The results show that both steric effects are a result of the change in strain during the reaction s = 2Hs(7) - Hs(1)>.A fraction of 0.5 - 0.6 of Ds contributes to ΔG excit. (150 deg C), thus effecting the rate of the reaction.The large positiv value of Ds for R2 = aryl e.g.Ds (1a) = 7.8 kcal/mol, results from a strong repulsion between R1 and R2 in 7 due to the coplanar arrangement of the aryl ring with the radical center. - The resonance effect on the rate of thermolysis has a similar magnitude for R2 = phenyl, p-X-C6H4 (X = Cl, OCH3, t-C4H9, C6H5) and 2-naphthyl, but is considerable stronger for R2 = 1-naphthyl.The measured effect corresponds to a resonance stabilisation of 1-naphthylmethyl radicals by additional 4.5 kcal/mol, compared to benzyl radicals.