51268-88-3

Usage

Uses

Used in Chemical Synthesis:
(+)-CIS-1(R),2(S)-1,2-DIHYDROXY-1,2-DIHYDRONAPHTHALENE is used as a key intermediate in the synthesis of various organic compounds, particularly those with pharmaceutical and industrial applications. Its unique structure allows for the creation of novel molecules with potential benefits in these fields.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (+)-CIS-1(R),2(S)-1,2-DIHYDROXY-1,2-DIHYDRONAPHTHALENE is used as a building block for the development of new drugs. Its chemical properties make it a valuable component in the design and synthesis of innovative therapeutic agents.
Used in Environmental Applications:
Due to its origin from Naphthalene, a compound found in tobacco smoke and urban air, (+)-CIS-1(R),2(S)-1,2-DIHYDROXY-1,2-DIHYDRONAPHTHALENE can be utilized in environmental applications, such as the development of methods to detect and mitigate the presence of harmful pollutants in the atmosphere.
Used in Material Science:
The unique properties of (+)-CIS-1(R),2(S)-1,2-DIHYDROXY-1,2-DIHYDRONAPHTHALENE also make it a candidate for use in the development of new materials with specific characteristics, such as improved strength, durability, or chemical resistance.

InChI:InChI=1/C10H10O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6,9-12H/t9-,10+/m0/s1

Upstream product

• 573-57-9 1,4-epoxy-1,4-dihydronaphthalene 
• 447-53-0 1,2-Dihydronaphthalene 
• 91-20-3 naphthalene 
• 524-42-5 1,2-naphthoquinone 
• 123849-23-0 (R)-(+)-1-hydroxy-1,2-dihydronaphthalene 

Downstream Products

• 57495-92-8 (1R,2S)-1,2,3,4-tetrahydronaphthalene-1,2-diol 
• 817555-48-9 1,2,3,4-tetrahydro-1,2,3,4-tetrahydroxynaphthalene 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 14211-53-1 cis-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene 
• 574-00-5 1,2-Dihydroxynaphthalene 
• 90-15-3 α-naphthol 
• 17180-88-0 (1R,2S)-(+)-naphthalene 1,2-oxide 
• 17180-88-0 (-)-(1S,2R)-naphthalene 1,2-oxide 
• 460740-17-4 (2S)-2-p-toluenesulphonyloxy-1,2,3,4-tetrahydronaphthalene 
• 530-91-6 (S)-2-tetralol 
• 2217-42-7 (2R)-2-amino-1,2,3,4-tetrahydronaphthalene 
• 91-20-3 naphthalene 
• 135-19-3 β-naphthol 

Relevant academic research and scientific papers

Rhodium(I)-catalyzed domino asymmetric ring opening/enantioselective isomerization of oxabicyclic alkenes with water

Water-induced asymmetric ring opening: Enantio-enriched 2-hydroxy-1-tetralones are formed from oxabicyclic alkenes through a novel RhI-catalyzed domino reaction. The proposed mechanism involves water-induced asymmetric ring opening to generate chiral trans-1,2-diol intermediates and subsequent enantioselective isomerization (see scheme). Copyright

Hyperaromatic stabilization of arenium ions

Benzene-cis- and trans-1,2-dihydrodiols undergo acid-catalyzed dehydration at remarkably different rates: kcis/ktrans = 4500. This is explained by formation of a β-hydroxycarbocation intermediate in different initial conformations, one of which is stabilized by hyperconjugation amplified by an aromatic no-bond resonance structure (HOC6H6 + HOC6H5 H+). MP2 calculations and an unfavorable effect of benzoannelation on benzenium ion stability, implied by pKR measurements of -2.3, -8.0, and -11.9 for benzenium, 1-naphthalenium, and 9-phenanthrenium ions, respectively, support the explanation.

Bio-inspired arene cis-dihydroxylation by a non-haem iron catalyst modeling the action of naphthalene dioxygenase

Reported in this paper is the first example of a biomimetic iron complex, ([FeII(TPA)(NCMe)2]2+ (TPA = tris(2-pyridylmethyl)amine), that catalyses the cis-dihydroxylation of an aromatic double bond, mimicking the action of

Biotransformation of phenanthrene and 1-methoxynaphthalene with Streptomyces lividans cells expressing a marine bacterial phenanthrene dioxygenase gene cluster.

The phdABCD gene cluster in a marine bacterium Nocardioides sp. strain KP7 codes for the multicomponent enzyme phenanthrene dioxygenase. phdA encoding an iron-sulfur protein large subunit alpha, phdB encoding its small subunit beta, phdC encoding ferredoxin, and phdD encoding ferredoxin reductase, were replaced in such a way that the termination codons of the preceding open reading frames were overlapped with the initiation codons of the following genes. This manipulated phdABCD gene cluster was positioned downstream of the thiostrepton-inducible promoter PtipA in a high-copy-number vector pIJ6021, and introduced into the gram-positive, soil-inhabiting, filamentous bacterium Streptomyces lividans. The recombinant S. lividans cells converted phenanthrene into a cis-diol form, which was determined to be cis-3,4-dihydroxy-3,4-dihydrophenanthrene by its UV spectral data as well as HPLC property, using the authentic sample for comparison. This biotransformation proceeded very efficiently; 200 microM and 2 mm of phenanthrene were almost completely converted to its cis-diol form in 6 h and 32 h, respectively. In addition, the S. lividans cells carrying the phdABCD gene cluster were found to transform 1-methoxynaphthalene to two products, which were identified to be 8-methoxy-2-naphthol in addition to 8-methoxy-1,2-dihydro-1,2-naphthalenediol by their EI-MS, 1H- and 13C-NMR spectral data.

Bioconversion of substituted naphthalenes to the corresponding 1,2-dihydro derivatives by Escherichia coli recombinant strains

1,2-dihydroxynaphthalenes are produced by bioconversion of the corresponding hydrocarbons using Escherichia coli recombinant strains containing the naphthalene dioxygenase and dehydrogenase genes cloned from pseudomonas fluorescens N3. Conversions are lead by a two step procedure without isolation of the dihydrodiol intermediate. Conversion rates depend on the position and nature of the naphthalene substituent.

Dioxygenase-catalysed oxidation of dihydronaphthalenes to yield arene hydrate and cis-dihydro naphthalenediols

Biotransformation of 1,2- and 1,4-dihydronaphthalene substrates, using growing cultures of Pseudomonas putida UV4, resulted in dioxygenase-catalysed benzylic monohydroxylation, cis-tetrahydro diol and cis-dihydro diol formation, trihydroxylation and dehydrogenation. The arene hydrates, (R)-1,2-dihydronaphthalen-1-ol 5 and (R)-1,4-dihydronaphthalen-1-ol 7, were isolated as enantiopure metabolites while 1,2-dihydronaphthalen-2-ol 8 was found in almost racemic form. The structure, enantiopurity and absolute stereochemistry of these arene hydrates of naphthalene were confirmed by chemical synthesis. Deuterium labelling studies, and the use of enantiomerically pure arene hydrates 5 and 7 as substrates, were used to establish the metabolic pathways for the formation of (1R,2S)-1,2-dihydronaphthalene-1,2-diols 2, from both 1,2-dihydronaphthalene 3 and 1,4-dihydronaphthalene 6 substrates.

Stereospecific Benzylic Hydroxylation of Bicyclic Alkenes by Pseudomonas putida: Isolation of (+)-R-1-Hydroxy-1,2-dihydronaphthalene, an Arene Hydrate of Naphthalene from Metabolism of 1,2-Dihydronaphthalene

Metabolism of the bicyclic alkenes 1,2-dihydronaphthalene, indene, and 1,2-benzocyclohepta-1,3-diene by a mutant strain of Pseudomonas putida yields benzylic monols (exclusively with R configuration) as metabolites and vicinal cis diols as minor products having an excess of the S configuration at the benzylic position.

Reduction of ortho-Quinones to Dihydrodiols

1,2-Naphthaquinone, 5-bromo-1,2-naphthaquinone and dibenzanthracene-3,4-quinone in the form of dibromo-intermediates were reduced to a mixture of cis- and trans-diols by the action of sodium borohydride in ethanol.An alternative synthesis of trans-3,4-dihydroxy-3,4-dihydrodibenzanthracene is also reported.