20107-40-8

Basic information

• Product Name: (S)-1,2,3,4-tetrahydronaphthalen-2-ol
• Synonyms: (S)-1,2,3,4-tetrahydronaphthalen-2-ol
• CAS NO: 20107-40-8
• Molecular Formula: C₁₀H₁₂O
• Molecular Weight: 148.20168
• Mol File: 20107-40-8.mol
• Article Data: 50

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-1,2,3,4-tetrahydronaphthalen-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1,2,3,4-tetrahydronaphthalen-2-ol(20107-40-8)
• EPA Substance Registry System: (S)-1,2,3,4-tetrahydronaphthalen-2-ol(20107-40-8)

Safety Data

• Hazardous Substances Data: 20107-40-8(Hazardous Substances Data)

Usage

Description

(S)-1,2,3,4-tetrahydronaphthalen-2-ol, also known as tetrahydronaphthalenol, is a chemical compound with the molecular formula C10H12O. It is a colorless liquid characterized by a slightly sweet, floral odor. (S)-1,2,3,4-tetrahydronaphthalen-2-ol is recognized for its versatility and holds significant importance across various industries due to its multiple applications.

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

• 766-77-8 Dimethylphenylsilane 
• 530-93-8 1,2,3,4-tetrahydronaphthalen-2-one 
• 57495-92-8 (1R,2S)-1,2,3,4-tetrahydronaphthalene-1,2-diol 
• 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 
• 115276-22-7 1,2-naphthaquinone 1-<(2S,3S)-1,4-dimethoxy-2,3-butylene>acetal 
• 71601-10-0 (RS)-1,2,3,4-tetrahydro-2-naphthol acetate 
• 530-91-6 1,2,3,4-tetrahydronaphthalen-2 ol 
• 939760-86-8 6,8-Difluoro-1,2-dihydro-naphthalene 
• 447-53-0 1,2-Dihydronaphthalene 
• 124867-52-3 C₁₆H₂₂O₅ 
• 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 

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 articles and documents

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.

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.