14211-53-1

Upstream product

• 2461-34-9 1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene 
• 64559-97-3 2-hydroxy-1-tetralone 
• 140134-31-2 (R)-(+)-2-hydroxy-3,4-dihydro-2H-naphthalen-1-one 
• 182822-22-6 (2S)-1-oxo-2-hydroxy-1,2,3,4-tetrahydronaphthalene 
• 529-33-9 1,2,3,4-Tetrahydro-1-naphthol 
• 447-53-0 1,2-Dihydronaphthalene 
• 7487-88-9 magnesium sulfate 
• 2018-87-3 1,2-dibromo-1,2,3,4-tetrahydro-naphthalene 
• 64-19-7 acetic acid 
• 524-42-5 1,2-naphthoquinone 
• 64245-04-1 2-bromo-1-hydroxy-1,2,3,4-tetrahydronaphthalene 
• 75-91-2 tert.-butylhydroperoxide 
• 2461-34-9 1,2-epoxy-3,4-dihydronaphthalene 
• 771-16-4 cis-1,2-dihydroxy-1,2-dihydronaphthalene 

Downstream Products

• 1346229-04-6 benzyl (1R,2R)-2-(benzyloxy)-1,2,3,4-tetrahydronaphthalen-1-ylcarbamate 
• 1346228-96-3 (1R,2R)-1,2-bis(benzyloxy)-1,2,3,4-tetrahydronaphthalene 
• 776-79-4 2-(2-carboxyethyl)benzoic acid 
• 530-93-8 1,2,3,4-tetrahydronaphthalen-2-one 
• 14807-28-4 2-(3-oxopropyl)benzaldehyde 
• 89920-57-0 (1S,2R)-cis-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene 
• 57495-92-8 (1R,2S)-1,2,3,4-tetrahydronaphthalene-1,2-diol 
• 7480-36-6 (+/-)-cis-1-amino-2-hydroxy-1,2,3,4-tetrahydronaphthalene 
• 54311-89-6 2-benzyl-2,3,4,5-tetrahydro-1H-benzo[c]azepine 
• 23190-43-4 (-)-(1S,2S)-trans-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene 
• 57496-61-4 (1R,2R)-trans-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene 
• 14211-53-1 cis-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene 
• 140134-31-2 (R)-(+)-2-hydroxy-3,4-dihydro-2H-naphthalen-1-one 
• 182822-22-6 (2S)-1-oxo-2-hydroxy-1,2,3,4-tetrahydronaphthalene 

Relevant academic research and scientific papers

Oxygenation of alkenes with t-BuOOH catalysed by β-cyclodextrin borate

β-Cyclodextrin borate catalyses oxygenation of aryl substituted alkenes in the presence of t-BuOOH to afford β-dioxy alcohols in good yields (63-86%).

Microbiological transformations. 31: Synthesis of enantiopure epoxides and vicinal diols using fungal epoxide hydrolase mediated hydrolysis

The enantioselective hydrolysis of epoxyindene and dihydronaphtalene epoxides by the fungus Beauveria sulfurescens (ATCC 7159) is described. This allowed the preparation of both these epoxides, as well as of the corresponding diols, in good to excellent enantiomeric purity.

β-Hydroxy carbocation intermediates in solvolyses of di- and tetra-hydronaphthalene substrates

Solvolysis of trichloroacetate esters of 2-methoxy-1,2-dihydro-1-naphthols shows a remarkably large difference in rates between the cis and trans isomers, kcis/ktrans = 1800 in aqueous acetonitrile. This mirrors the behaviour of the acid-catalysed dehydration of cis- and trans-naphthalene-1, 2-dihydrodiols to form 2-naphthol, for which kcis/ktrans = 440, but contrasts with that for solvolysis of tetrahydronaphthalene substrates, 1-chloro-2-hydroxy-1,2,3,4-tetrahydronaphthalenes, for which k cis/ktrans = 0.5. Evidence is presented showing that the trans isomer of the dihydro substrates reacts unusually slowly rather than the cis isomer unusually rapidly. Comparison of rates of solvolysis of 1-chloro-1,2,3,4-tetrahydronaphthalene and the corresponding (cis) substrate with a 2-hydroxy group indicates that a β-OH slows the reaction by nearly 2000-fold, which represents a typical inductive effect characteristic also of cis-dihydrodiol substrates. The slow reaction of the trans-dihydrodiol substrate is consistent with initial formation of a β-hydroxynaphthalenium carbocation with a conformation in which a C-OH occupies an axial position β to the carbocation centre preventing stabilisation of the carbocation by C-H hyperconjugation, which would occur in the conformation initially formed from the cis isomer. It is suggested that C-H hyperconjugation is particularly pronounced for a β-hydroxynaphthalenium ion intermediate because the stability of its no-bond resonance structure reflects the presence of an aromatic naphthol structure.

Verification of the Major Metabolic Oxidation Path for the Naphthoyl Group in Chemoattractant Receptor-Homologous Molecule Expressed on Th2 Cells (CRTh2) Antagonist 2-(2-(1-Naphthoyl)-8-fluoro-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)acetic Acid (Setipiprant/ACT-129968)

Various racemic and enantioenriched (trans)-X,Y-dihydroxy-X,Y-dihydronaphthoyl analogues as well as X-hydroxy-naphthoyl analogues of CRTh2 antagonist 2-(2-(1-naphthoyl)-8-fluoro-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)acetic acid (1, Setipiprant/ACT-129968) were synthesized in order to gain insight into regio- and enantioselectivity of the metabolic oxidation of 1 and to verify the structures of four metabolites that were proposed earlier in a clinical ADME study. Analytical data of the synthetic standards were compared with data from samples of biological origin. The two major metabolites M7 and M9 were unambiguously verified as 2-(2-((trans)-3,4-dihydroxy-3,4-dihydronaphthalene-1-carbonyl)- and 2-(2-((trans)-5,6-dihydroxy-5,6-dihydronaphthalene-1-carbonyl)-8-fluoro-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)acetic acid, respectively, each composed of two enantiomers with 68% and 44% ee in favor of (+)-(3S,4S)-M7 and (+)-(5S,6S)-M9, respectively. Likewise, minor metabolites M3 and M13 were identified as 2-(8-fluoro-2-(5-hydroxy-1-naphthoyl)- and 2-(8-fluoro-2-(4-hydroxy-1-naphthoyl)-1,2,3,4-tetrahydro-5H-pyrido[4,3-b]indol-5-yl)acetic acid, respectively.

New chiral synthons from the microbial oxidation of bromonaphthalenes

1-Bromo- and 2-bromonaphthalene were subjected to bio-oxidation with whole cells of Pseudomonas putida NCIB 9816-11. The major metabolites were isolated and spectroscopically characterized as (+)-cis-(1R,2S)-Dihydroxy-1,2-dihydro-8-bromonaphthalene 1, (+)-cis-(1R,2S)-Dihydroxy-1,2-dihydro-5-bromonaphthalene 2 from 1-bromonaphthalene and (+)-cis-(1R,2S)-Dihydroxy-1,2-dihydro-7-bromonaphthalene 8 from 2-bromonaphthalene. The absolute stereochemistry and enantiomeric excess were determined by conversion of each metabolite to the known (-)-cis-tetrahydronaphthalene diol 6.

A de novo synthetic method to the access of N-substituted benzazepines

A novel, convenient procedure has been described for the construction of fluorine-containing benzazepines. The synthetic protocol starting from readily available dihydronaphthalene regioisomers is based on oxidative ring olefin bond cleavage followed by r

Enantioselective, Stereoconvergent Resolution Copolymerization of Racemic cis-Internal Epoxides and Anhydrides

Unprecedented enantioselective resolution copolymerization of racemic cis-internal epoxides and anhydrides was mediated by dinuclear aluminum complexes with multiple chirality, affording optically active polyesters with two contiguous stereogenic centers, and the unreacted substrates in good enantioselectivity. Unexpected stereoconvergence is observed in this resolution copolymerization, where the selectivity factor for the enantioselective formation of copolymer significantly exceeds the kinetic resolution coefficient based on the unreacted epoxide at various conversions. Catalytic activity and copolymer enantioselectivity are strongly influenced by the phenolate ortho-substituents of the ligand set, as well as the axial linker and its chirality. An enantiopure binaphthol-linked bimetallic AlIII complex allows stereoconvergent access to the stereoregular semi-crystalline polyesters and a concomitant kinetic resolution of the epoxide substrates.

Iodine-Initiated Dioxygenation of Aryl Alkenes Using tert-Butylhydroperoxides and Water: A Route to Vicinal Diols and Bisperoxides

An environment-friendly and efficient dioxygenation of aryl alkenes for the construction of vicinal diols has been developed in water with iodine as the catalyst and tert-butylhydroperoxides (TBHPs) as the oxidant. The protocol was efficient, sustainable, and operationally simple. Detailed mechanistic studies indicated that one of the hydroxyl groups is derived from water and the other one is derived from TBHP. Additionally, the bisperoxides could be obtained in good yields with iodine as the catalyst, Na2CO3 as the additive, and propylene carbonate as the solvent, instead.

Regioselective biocatalytic self-sufficient Tishchenko-type reactionviaformal intramolecular hydride transfer

A self-sufficient nicotinamide-dependent intramolecular bio-Tishchenko-type reaction was developed. The reaction is catalyzed by alcohol dehydrogenases and proceeds through formal intramolecular hydride transfer on dialdehydes to deliver lactones. Regioselectivity on [1,1′-biphenyl]-2,2′-dicarbaldehyde substrates could be controlledviathe electronic properties of the substituents. Preparative scale synthesis provided access to substituted dibenzo[c,e]oxepin-5(7H)-ones.

Oxidative β-Halogenation of Alcohols: A Concise and Diastereoselective Approach to Halohydrins

β-Halohydrins bearing transformable halo- and hydroxyl groups, are easily converted into various valuable blocks in organic and pharmaceutical synthesis. A diastereoselective β-halogenation of benzylic alcohols was achieved under simple and low-cost conditions, which provided a direct synthesis of β-halohydrins. The simple reaction conditions, easily available reagents, high diastereoselectivities, and additional oxidant-free make this reaction very attractive and practical.