14211-53-1

Basic information

• Product Name: rel-Tetralin-1β*,2α*-diol
• Synonyms: rel-Tetralin-1β*,2α*-diol
• CAS NO: 14211-53-1
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.2011
• Mol File: 14211-53-1.mol
• Article Data: 33

Chemical Properties

• Boiling Point: 308.4°Cat760mmHg
• Flash Point: 151.7°C
• Appearance: /
• Density: 1.26g/cm³
• CAS DataBase Reference: rel-Tetralin-1β*,2α*-diol(CAS DataBase Reference)
• NIST Chemistry Reference: rel-Tetralin-1β*,2α*-diol(14211-53-1)
• EPA Substance Registry System: rel-Tetralin-1β*,2α*-diol(14211-53-1)

Safety Data

• Hazardous Substances Data: 14211-53-1(Hazardous Substances Data)

Upstream product

• 75-91-2 tert.-butylhydroperoxide 
• 447-53-0 1,2-Dihydronaphthalene 
• 18672-77-0 2-acetoxy-3,4-dihydronaphthalen-1(2H)-one 
• 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 
• 2461-34-9 1,2-epoxy-3,4-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 
• 2018-87-3 (+/-)-trans-1,2-dibromo-1,2,3,4-tetrahydronaphthalene 
• 771-16-4 cis-1,2-dihydroxy-1,2-dihydronaphthalene 

Downstream Products

• 776-79-4 2-(2-carboxyethyl)benzoic acid 
• 530-93-8 1,2,3,4-tetrahydronaphthalen-2-one 
• 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 
• 14807-28-4 2-(3-oxopropyl)benzaldehyde 
• 54311-89-6 2-benzyl-2,3,4,5-tetrahydro-1H-benzo[c]azepine 
• 1346228-96-3 (1R,2R)-1,2-bis(benzyloxy)-1,2,3,4-tetrahydronaphthalene 
• 1346229-04-6 benzyl (1R,2R)-2-(benzyloxy)-1,2,3,4-tetrahydronaphthalen-1-ylcarbamate 
• 7480-36-6 (+/-)-cis-1-amino-2-hydroxy-1,2,3,4-tetrahydronaphthalene 
• 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 

Relevant articles and documents

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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%).

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.

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.

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.

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.