79560-27-3

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 13139-86-1 4-methoxyphenyl magnesium bromide 

Downstream Products

• 21855-80-1 4-(3,4-dihydronaphthalen-1-yl)phenyl methyl ether 
• 19353-89-0 1-(4-methoxyphenyl)-1,2,3,4-tetrahydronaphthalene 
• 79560-28-4 4-hydroxy-4-(4-methoxyphenyl)-1-tetralone 
• 79560-29-5 N-methyl-4-hydroxy-4-(4-methoxyphenyl)-1,2,3,4-tetrahydro-1-naphthalenamine 
• 79560-31-9 N-methyl-4-(4-methoxyphenyl)-1,2-dihydro-1-naphthalenamine hydrochloride 
• 79560-05-7 cis-N-methyl-4-(methoxyphenyl)-1,2,3,4-tetrahydro-1-naphthalenamine hydrochloride 
• 79836-63-8 trans-N-methyl-4-(methoxyphenyl)-1,2,3,4-tetrahydro-1-naphthalenamine hydrochloride 
• 3771-17-3 4-(1,2,3,4-tetrahydro-1-naphthyl)-phenol 
• 110690-19-2 2-(p-methoxyphenylhydroxymethyl)phenylpropanol 
• 117266-89-4 (p-methoxyphenyl)-1-homoisochroman 

Relevant academic research and scientific papers

Effect of methoxyl groups on the NMR spectra: configuration and conformation of natural and synthetic indanic and tetralinic structures

Here, we studied the influence of the methoxyl groups attached at C-7 and C-2′ of natural and synthetic 1-arylindanes on the chemical shift of the signal of bibenzylic hydrogen and carbon atoms and J1,2 coupling constants. This influence was also analysed in natural 1-aryltetralins and related compounds that possess methoxyl and/or hydroxyl groups bound at C-8 and C-2′. The methoxyl groups attached at C-7 in indanes or at C-8 in tetralins produce a deshielding signal at H-1 and shield at C-1 and a strong decrease in the value of J1,2 due to the pseudoequatorial location adopted by the aryl group bound at C-1, avoiding an ‘A1,3 strain’. Furthermore, compounds with hydroxyl or methoxyl groups in C-2′, in the absence of substituents of C-7 or C-8, present a strong deshielding signal at H-1, strong shield of the C-1 signal and a decrease in the value of J1,2. This is attributed to the stereoelectronic effects of the methoxyl or hydroxyl groups, which we have called ‘Asarone effect’. NOESY experiments were conducted to confirm the configuration and conformation of some of the compounds included in this work. This study shows that both effects, A1,3 strain and Asarone effect, must be taken into account when the structure of natural indanes and tetralins is analysed by using 1H-NMR and 13C-NMR spectra. Copyright

A mild dihydrobenzooxaphosphole oxazoline/iridium catalytic system for asymmetric hydrogenation of unfunctionalized dialins

Air-stable P-chiral dihydrobenzooxaphosphole oxazoline ligands were designed and synthesized. When they were used in the iridium-catalyzed asymmetric hydrogenation of unfunctionalized 1-aryl-3,4-dihydronaphthalenes under one atmosphere pressure of H2, up to 99:1 e.r. was obtained. High enantioselectivities were also observed in the reduction of the exocyclic imine derivatives of 1-tetralones.

Dynamic kinetic resolution-asymmetric transfer hydrogenation of 1-aryl-substituted cyclic ketones

A range of 1-aryl-2-tetranols, and 1-phenyl-2-indanol, have been generated in high yield and enantiomeric excess from the corresponding racemic ketones, via a dynamic kinetic resolution-transfer hydrogenation process, using Ru(II)-TsDPEN in formic acid/triethylamine (5:2). This provides a potential entry to an asymmetric total synthesis of benzazepines such as Sch 39166.

Hydroxy substituted phenyltetralines: compounds with affinity for estrogen and androgen receptors

Among nonsteroidal antiandrogens, mostly compounds of the Flutamide-type are described. For the development of new compounds with affinity to androgen receptors and antiandrogenic activity five new hydroxy-substituted phenyltetralines were prepared and te

ORTHO-SUBSTITUTED PHENYLPROPIONIC ACIDS. PART I. CYCLIZATION OF SOME 2-ACYLPHENYLPROPIONIC ACIDS TO HOMOISOCHROMAN DERIVATIVES

Some homoisochroman derivatives from the corresponding 2-(phenylhydroxymethyl)phenylpropanols were obtained.The latter compounds were prepared from 2-acylphenylpropionic acids.

Nontricyclic Antidepressant Agents Derived from cis- and trans-1-Amino-4-aryltetralins

The need for drugs that lack the obtrusive and limiting side effects of the tricyclic antidepressants has prompted the search for agents with greatly enhanced selectivity for specific mechanisms believed to be essential for antidepressant efficacy.The potential role of derangements of 5-HT pathways in the etiology of depression has long been suspected and has given impetus to the development of newer compounds that accentuate inhibition of serotonin reuptake.This paper presents structure-activity relationship for a series of cis-1-amino-4-(substituted-aryl)tetralins, which are surprisingly potent and selective inhibitors of serotonin uptake in in vitro models.These compounds are pharmacologically distinct from corresponding members of the trans series, which also potently block uptake of dopamine and norepinephrine.The activity in both cis and trans series is stereospecific, being restricted to the cis-(1S,4S) and the trans-(1R,4S) enantiomers.