57495-92-8

Usage

Uses

Used in Pharmaceutical Industry:
(+)-CIS-1(R),2(S)-1,2-DIHYDROXY-1,2,3,4-TETRAHYDRONAPHTHALENE is used as a chiral building block for the synthesis of various drugs, contributing to the development of new therapeutic agents.
Used as an Antiviral Agent:
In the field of antiviral research, (+)-CIS-1(R),2(S)-1,2-DIHYDROXY-1,2,3,4-TETRAHYDRONAPHTHALENE has shown potential as an antiviral agent, offering a promising direction for the treatment of viral infections.
Used in Organic Synthesis:
(+)-CIS-1(R),2(S)-1,2-DIHYDROXY-1,2,3,4-TETRAHYDRONAPHTHALENE is utilized as a chiral building block in organic synthesis, enabling the creation of enantiomerically pure compounds for various applications.
Used as a Ligand in Asymmetric Catalysis:
In the realm of asymmetric catalysis, (+)-CIS-1(R),2(S)-1,2-DIHYDROXY-1,2,3,4-TETRAHYDRONAPHTHALENE serves as a ligand, facilitating the synthesis of enantioselective products with improved yields and selectivity.

InChI:InChI=1/C10H12O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-4,9-12H,5-6H2

Upstream product

• 2461-34-9 1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 2461-34-9 (1R,2S)-1,2-epoxy-3,4-dihydronaphthalene 
• 51268-88-3 (1R,2S)-1,2-dihydronaphthalene-1,2-diol 
• 447-53-0 1,2-Dihydronaphthalene 
• 174814-12-1 (+)-cis-(1R,2S)-dihydroxy-1,2-dihydro-7-bromonaphthalene 
• 197140-92-4 (-)-(S)-1,2,3,4-tetrahydro-1-oxonaphthalen-2-yl acetate 
• 18672-77-0 2-acetoxy-3,4-dihydronaphthalen-1(2H)-one 
• 2018-87-3 1,2-dibromo-1,2,3,4-tetrahydro-naphthalene 
• 64-19-7 acetic acid 
• 7487-88-9 magnesium sulfate 
• 2018-87-3 (+/-)-trans-1,2-dibromo-1,2,3,4-tetrahydronaphthalene 
• 64245-04-1 2-bromo-1-hydroxy-1,2,3,4-tetrahydronaphthalene 
• 64559-97-3 2-hydroxy-1-tetralone 

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 
• 530-93-8 1,2,3,4-tetrahydronaphthalen-2-one 
• 89920-57-0 (1S,2R)-cis-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene 
• 7480-36-6 (+/-)-cis-1-amino-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 
• 776-79-4 2-(2-carboxyethyl)benzoic acid 
• 27916-44-5 3-(2-formylphenyl)propanoic acid 
• 25040-17-9 methyl 3-[2-(methoxycarbonyl)phenyl]propionate 
• 17180-88-0 (1R,2S)-(+)-naphthalene 1,2-oxide 
• 17180-88-0 (-)-(1S,2R)-naphthalene 1,2-oxide 
• 426262-25-1 (1S,2S)-2-p-toluenesulphonyloxy-1-azido-1,2,3,4-tetrahydronaphthalene 
• 460740-17-4 (2S)-2-p-toluenesulphonyloxy-1,2,3,4-tetrahydronaphthalene 

Relevant academic research and scientific papers

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.

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

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.

Enantioselective Dihydroxylation of Alkenes Catalyzed by 1,4-Bis(9-O-dihydroquinidinyl)phthalazine-Modified Binaphthyl–Osmium Nanoparticles

A series of unprecedented binaphthyl–osmium nanoparticles (OsNPs) with chiral modifiers were applied in the heterogeneous asymmetric dihydroxylation of alkenes. A remarkable size effect of the OsNPs, depending on the density of the covalent organic shells, on the reactivity and enantioselectivity of the dihydroxylation reaction was revealed. Successful recycling of the OsNPs was also demonstrated and high reaction efficiency and enantioselectivity were maintained.

Carbohydrate/DBU Cocatalyzed Alkene Diboration: Mechanistic Insight Provides Enhanced Catalytic Efficiency and Substrate Scope

A mechanistic investigation of the carbohydrate/DBU cocatalyzed enantioselective diboration of alkenes is presented. These studies provide an understanding of the origin of stereoselectivity and also reveal a strategy for enhancing reactivity and broadening the substrate scope.

Multivariate Metal-Organic Frameworks as Multifunctional Heterogeneous Asymmetric Catalysts for Sequential Reactions

The search for versatile heterogeneous catalysts with multiple active sites for broad asymmetric transformations has long been of great interest, but it remains a formidable synthetic challenge. Here we demonstrate that multivariate metal-organic frameworks (MTV-MOFs) can be used as an excellent platform to engineer heterogeneous catalysts featuring multiple and cooperative active sites. An isostructural series of 2-fold interpenetrated MTV-MOFs that contain up to three different chiral metallosalen catalysts was constructed and used as efficient and recyclable heterogeneous catalysts for a variety of asymmetric sequential alkene epoxidation/epoxide ring-opening reactions. Interpenetration of the frameworks brings metallosalen units adjacent to each other, allowing cooperative activation, which results in improved efficiency and enantioselectivity over the sum of the individual parts. The fact that manipulation of molecular catalysts in MTV-MOFs can control the activities and selectivities would facilitate the design of novel multifunctional materials for enantioselective processes.

Production Of Enantiopure alpha-Hydroxy Carboxylic Acids From Alkenes By Cascade Biocatalysis

The invention provides compositions comprising an alkene epoxidase and a selective epoxide hydrolase, such as a recombinant microorganism comprising a first heterologous nucleic acid encoding an alkene epoxidase and a second heterologous nucleic acid encoding a selective epoxide hydrolase. Exemplary alkene epoxidases include StyAB, while exemplary selective epoxide hydrolases include epoxide hydrolases from Sphingomonas, Solanum tuberosum, or Aspergillus. The invention also provides non-toxic methods of making enantiomerically pure vicinal diols or enantiomerically pure alpha-hydroxy carboxylic acids using these compositions and microorganisms.

Highly Enantioselective Iron-Catalyzed cis-Dihydroxylation of Alkenes with Hydrogen Peroxide Oxidant via an FeIII-OOH Reactive Intermediate

The development of environmentally benign catalysts for highly enantioselective asymmetric cis-dihydroxylation (AD) of alkenes with broad substrate scope remains a challenge. By employing [FeII(L)(OTf)2] (L=N,N′-dimethyl-N,N′-bis(2-methyl-8-quinolyl)-cyclohexane-1,2-diamine) as a catalyst, cis-diols in up to 99.8 % ee with 85 % isolated yield have been achieved in AD of alkenes with H2O2as an oxidant and alkenes in a limiting amount. This “[FeII(L)(OTf)2]+H2O2” method is applicable to both (E)-alkenes and terminal alkenes (24 examples >80 % ee, up to 1 g scale). Mechanistic studies, including18O-labeling, UV/Vis, EPR, ESI-MS analyses, and DFT calculations lend evidence for the involvement of chiral FeIII-OOH active species in enantioselective formation of the two C?O bonds.