19216-89-8

Usage

Chirality

Chiral derivative of naphthalene

Optical activity

(1R,2R)-(-)indicates the specific configuration of the molecule and its optical activity

Synonyms

(R,R)-(+)-1,2-Dihydro-1,2-naphthalenediol

Applications

a. Organic synthesis
b. Chiral ligand in asymmetric catalysis
c. Pharmaceutical industry
d. Chemical industry
e. Production of fine chemicals and pharmaceutical intermediates

Biological activity

Exhibits biological activity with potential uses in medicinal applications

Upstream product

• 573-57-9 1,4-epoxy-1,4-dihydronaphthalene 
• 91-20-3 naphthalene 
• 524-42-5 1,2-naphthoquinone 

Downstream Products

• 90-15-3 α-naphthol 
• 574-00-5 1,2-Dihydroxynaphthalene 
• 135-19-3 β-naphthol 
• 14211-53-1 cis-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 91-20-3 naphthalene 

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.

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.