20107-40-8

Usage

Uses

Used in Fragrance and Flavor Industry:
(S)-1,2,3,4-tetrahydronaphthalen-2-ol is used as a key component in the production of fragrances and flavors, capitalizing on its appealing scent and taste. Its natural, floral aroma makes it a popular choice for enhancing the sensory qualities of perfumes and personal care products.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, (S)-1,2,3,4-tetrahydronaphthalen-2-ol serves as a chiral synthesis intermediate. Its unique structure allows it to be a valuable building block in the creation of more complex organic compounds, contributing to the development of new medications and therapies.
Used in Chemical Synthesis:
Furthermore, (S)-1,2,3,4-tetrahydronaphthalen-2-ol is utilized as a fundamental building block in the synthesis of other organic compounds. Its chemical properties make it a suitable candidate for various chemical reactions, leading to the production of a wide range of products with diverse applications.

Upstream product

• 115276-22-7 1,2-naphthaquinone 1-<(2S,3S)-1,4-dimethoxy-2,3-butylene>acetal 
• 530-93-8 1,2,3,4-tetrahydronaphthalen-2-one 
• 447-53-0 1,2-Dihydronaphthalene 
• 766-77-8 Dimethylphenylsilane 
• 108-05-4 vinyl acetate 
• 530-91-6 1,2,3,4-tetrahydronaphthalen-2 ol 
• 51268-88-3 (1R,2S)-1,2-dihydronaphthalene-1,2-diol 
• 7576-04-7 (R)-(Indanylcarbinyl-1)-p-toluolsulfonat 
• 115276-25-0 2R-2-hydroxyl (2H)-naphthalenone (2S,3S)-1,4-dimethoxy-2,3-butylene acetal 
• 71601-10-0 (RS)-1,2,3,4-tetrahydro-2-naphthol acetate 
• 1130490-92-4 4,4,5,5-tetramethyl-2-(1,2,3,4-tetrahydronaphthalen-2-yl)-1,3,2-dioxaborolane 
• 939760-68-6 4,6-Difluoro-1a,2,3,7b-tetrahydro-1-oxa-cyclopropa[a]naphthalene 
• 173996-16-2 5,7-Difluoro-1,2,3,4-tetrahydro-naphthalen-1-ol 
• 939760-86-8 6,8-Difluoro-1,2-dihydro-naphthalene 

Downstream Products

• 1374428-96-2 (S)-((S)-1,2,3,4-tetrahydronaphthalen-2-yl) 3,3,3-trifluoro-2-methoxy-2-phenylpropanoate 
• 2217-42-7 (2R)-2-amino-1,2,3,4-tetrahydronaphthalene 

Relevant academic research and scientific papers

Organic-inorganic nanocrystal reductase to promote green asymmetric synthesis

An acetophenone reductase from Geotrichum candidum (GcAPRD) was immobilized by the organic-inorganic nanocrystal method. The GcAPRD nanocrystal presented improved stability and recyclability compared with those of the free GcAPRD. Moreover, the GcAPRD nanocrystal reduced broad kinds of ketones with excellent enantioselectivities to produce beneficial chiral alcohols such as (S)-1-(3′,4′-dichlorophenyl)ethanol with >99% yield and >99% ee. The robust and versatile properties of the GcAPRD nanocrystal demonstrated an approach to promote green asymmetric synthesis and sustainable chemistry. This journal is

Access to both enantiomers of substituted 2-tetralol analogs by a highly enantioselective reductase

Both (S) and (R) forms of enantiomerically pure 2-tetralols, and their substituted analogs, are fundamental pharmaceutical intermediates. Here, we utilized the wild type and an engineered form of a highly enantioselective acetophenone reductase from Geotrichum candidum NBRC 4597 (GcAPRD) to produce (S)- and (R)-2-tetralols, and their substituted analogs. All mutations targeted residue Trp288, which has been shown to restrict substrate binding, but not play a direct role in catalysis. The wild type produced (S)-alcohols with excellent enantioselectivity, while the engineered forms produced either (S)- or (R)- alcohols, depending on the substituent on the aromatic ring of the substrate, indicating that enantioselectivity can be rationally controlled. As a result, we were able to produce 6-hydroxy-2-tetralol, a potential antifungal drug intermediate, with 98% ee (S) and 81% ee (R) by wild type and Trp288Ser GcAPRD, respectively. To our knowledge, this is the first report of generating chiral 6-hydroxy-2-tetralol by rational enzyme design.

Identification of an Esterase Isolated Using Metagenomic Technology which Displays an Unusual Substrate Scope and its Characterisation as an Enantioselective Biocatalyst

Evaluation of an esterase annotated as 26D isolated from a marine metagenomic library is described. Esterase 26D was found to have a unique substrate scope, including synthetic transformations which could not be readily effected in a synthetically useful manner using commercially available enzymes. Esterase 26D was more selective towards substrates which had larger, more sterically demanding substituents (i. e. iso-propyl or tert-butyl groups) on the β-carbon, which is in contrast to previously tested commercially available enzymes which displayed a preference for substrates with sterically less demanding substituents (e.g. methyl group) at the β-carbon. (Figure presented.).

Chiral (cyclopentadienone)iron complexes with a stereogenic plane as pre-catalysts for the asymmetric hydrogenation of polar double bonds

In this paper, we describe a small library of easy-to-prepare chiral (cyclopentadienone)iron pre-catalysts for enantioselective C[dbnd]O and C[dbnd]N hydrogenations. Starting from readily accessible achiral materials, six chiral (cyclopentadienone)iron complexes (1a-f) possessing a stereogenic plane were synthesized in racemic form. Based on the screening of pre-catalysts (±)-1a-f in the hydrogenation of ketones and ketimines, we selected two complexes (1a and 1d) for resolution by semipreparative enantioselective HPLC. The absolute configuration of the separated enantiomers of 1a and 1d was assigned by XRD analysis (1a) and by comparison between experimental and DFT-calculated ECD and ORD spectra (1d). The enantiopure pre-catalysts (S)-1a and (R)-1d were tested in the asymmetric hydrogenation of several ketones and ketimines and showed good activity and modest enantioselectivity, the e.e. values ranging from very low to moderate (54%).

Enantioselective Synthesis of Boryl Tetrahydroquinolines via Cu-Catalyzed Hydroboration

A Cu-catalyzed regio- and enantioselective hydroboration of 1,2-dihydroquinolines with high yields and excellent enantioselectivities (up to 98% ee) was presented. This method could be applied in the asymmetric synthesis of the important intermediates used in the enantioselective synthesis of the potential agent Sumanirole for the treatment of Parkinson's disease and of the potentially interesting positive inotropic agent (S)-903.

Asymmetric Transfer Hydrogenation of (Hetero)arylketones with Tethered Rh(III)-N-(p-Tolylsulfonyl)-1,2-diphenylethylene-1,2-diamine Complexes: Scope and Limitations

A series of new tethered Rh(III)/Cp? complexes containing the N-(p-tolylsulfonyl)-1,2-diphenylethylene-1,2-diamine ligand have been prepared, characterized, and evaluated in the asymmetric transfer hydrogenation (ATH) of a wide range of (hetero)aryl ketones. The reaction was performed under mild conditions with the formic acid/triethylamine (5:2) system as the hydrogen source and provided enantiomerically enriched alcohols with good yields and high to excellent enantioselectivities. Although the nature of the substituents on the phenyl tethering ring did not alter the stereochemical outcome of the reaction, complexes bearing electron-donating groups exhibited a higher catalytic activity than those having electron-withdrawing groups. A scale-up of the ATH of 4-chromanone to the gram scale quantitatively delivered the reduced product with excellent enantioselectivity, demonstrating the potential usefulness of these new complexes.

Ansa-Ruthenium(II) Complexes of R2NSO2DPEN-(CH2)n(η6-Aryl) Conjugate Ligands for Asymmetric Transfer Hydrogenation of Aryl Ketones

New 3rd generation designer ansa-ruthenium(II) complexes featuring N,C-alkylene-tethered N,N-dialkylsulfamoyl-DPEN/η6-arene ligands, exhibited good catalytic performance in the asymmetric transfer hydrogenation (ATH) of various classes of (het)aryl ketones in formic acid/triethylamine mixture. In particular, benzo-fused cyclic ketones furnished 98 to >99.9% ee using a low catalyst loading.

Chiral Cyclopentadienone iron complexes for the catalytic asymmetric hydrogenation of ketones

Three chiral (cyclopentadienone)iron complexes derived from (R)-BINOL (CK1-3) were synthesized and their structures unambiguously confirmed by X-ray analysis (CK3). Under suitable conditions for the in situ conversion into the corresponding (hydroxycyclopentadienyl)iron hydrides (Me3NO, H2), the new chiral complexes were tested in the catalytic asymmetric hydrogenation of ketones, showing moderate to good enantioselectivity. In particular, the complex bearing methoxy substituents at the 3,3-positions of the binaphthyl moiety (CK2) proved remarkably more enantioselective than the unsubstituted one (CK1) and reached the highest level of enantioselectivity (up to 77% ee) ever obtained with chiral (cyclopentadienone)iron complexes. Reducto! Chiral (cyclopentadienone)iron complexes were synthesized and tested, after in situ activation, in the catalytic asymmetric hydrogenation of ketones leading to the highest enantiomeric excesses ever obtained with this type of catalysts.

Preparation of chiral ligands connected with quaternary ammonium group for recyclable catalytic asymmetric transfer hydrogenation in ionic liquid

Reuse of chiral ruthenium catalyst in catalytic asymmetric transfer hydrogenation (CATH) has attracted attention from economic and environmental viewpoints, and reactions using ionic liquids (ILs) as solvent are recognized as one of the most useful methods for reuse of the catalyst. We synthesized (1 S,2 S )- N-( p - toluenesulfonyl)-1,2-diphenylethylenediamine (TsDPEN) derivatives with various ionic moieties, and investigated the effect of their structure with respect to catalytic ability and recyclability in CATH with ILs. Ligand 3a having an imidazolium group showed the best results, and significant differences were observed depending on the structure of the ionic moiety or the length of the alkyl chain connecting the ligand site and the ionic moiety. Among various prochiral ketones used as substrates at various cycles, 3a showed a relatively good result.

Synthesis of (R)-BINOL-Derived (Cyclopentadienone)iron Complexes and Their Application in the Catalytic Asymmetric Hydrogenation of Ketones

A family of chiral (cyclopentadienone)iron complexes, featuring an (R)-BINOL-derived backbone, and their application in the asymmetric hydrogenation of ketones are described. The complexes differ from each other in the substituents at the 3,3′-positions of the binaphthyl residue (H, OH, OR, OCOR, OSO2R) or at the 2,5-positions of the cyclopentadienone ring [trimethylsilyl (TMS) or Ph]. Remarkably, eight precatalysts with different 3,3′-binaphthyl substitution [(R)-1c-1j] were synthesized from a common parent complex [(R)-1b] through direct functional group interconversion reactions of the complexes. The 3,3′-(bis)methoxy-substituted precatalyst (R)-1b gave the best catalytic performance, and its application scope was assessed in the hydrogenation of several ketones. The observed ee values (up to 77%) are much higher than those previously reported for other chiral (cyclopentadienone)iron complexes.