40316-60-7

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
Thiochroman-4-ol is used as a building block in the synthesis of pharmaceuticals and agrochemicals for its potential to contribute to the development of new therapeutic agents and agricultural products.
Used in Drug Discovery and Development:
Thiochroman-4-ol is utilized as a starting material for the production of novel compounds with therapeutic potential, owing to its diverse biological activities and unique molecular structure.
Used in Fragrance and Flavor Industry:
Due to its aromatic properties, Thiochroman-4-ol has been investigated for its potential use in the fragrance and flavor industry, where it could be employed to create new scents and tastes for various applications.

InChI:InChI=1/C9H10OS/c10-8-5-6-11-9-4-2-1-3-7(8)9/h1-4,8,10H,5-6H2

Upstream product

• 3528-17-4 2,3-dihydro-4H-[1]benzothiopyran-4-one 
• 76-86-8 Triphenylsilyl chloride 
• 94442-86-1 thiochroman-4-yl acetate 
• 108-05-4 vinyl acetate 
• 40316-60-7 (S)-3,4-dihydro-2H-thiochromen-4-ol 

Downstream Products

• 3528-17-4 2,3-dihydro-4H-[1]benzothiopyran-4-one 
• 40316-60-7 (R)-3,4-dihydro-2H-thiochromen-4-ol 
• 40316-60-7 (S)-3,4-dihydro-2H-thiochromen-4-ol 
• 1313511-66-8 C₂₇H₂₄OSSi 
• 94442-86-1 thiochroman-4-yl acetate 
• 106-44-5 p-cresol 
• 90-15-3 α-naphthol 
• 254-37-5 2H-thiochromene 
• 254-36-4 4H-thiochromene 

Relevant academic research and scientific papers

Studies on the intramolecular oxa-Pictet-Spengler rearrangement of 5-aryl-1,3-dioxolanes to 4-hydroxy-isochromans

The success and stereochemical outcome of the TiCl4-promoted oxa-Pictet-Spengler cyclization of 5-aryl-1,3-dioxolanes to produce 1,3-disubstituted-4-hydroxy-isochromans, is influenced by the length and nature of the side chains bound to C-2 and C-4 of the dioxolane. Methyl groups yield a mixture of 4-hydroxy-isochromans in which the 1,3-trans diastereomer predominates, while bulkier substituents give 1,3-cis diastereomers. Functional groups in the C-2 side chain of the dioxolane ring may hinder cyclization by complexation with the promoter.

Practical access to (S)-heterocyclic aromatic acetates via CAL-B/Na2CO3-deacylation and Mitsunobu reaction protocol

Herein, we report the preparation of enantiomerically pure forms of 2,3-dihydrobenzofuran-3-ol (1), chroman-4-ol (2), thiochroman-4-ol (3), 1-(furan-2-yl) ethanol (5) and 1-(thiophen-2-yl) ethanol (6), through a kinetic resolution catalysed by Candida antarctica lipase B/Na2CO3 hydrolysis sequence in organic media. The (R)-furnished alcohols and the (S)-remained acetates are recovered enantiopures (ee?>99%, E???200, Conv = 50%). Those ideal enzymatic kinetic resolution (EKRs) are well incorporated to the Mitsunobu inversion protocol in a one pot procedure to give (S)-heterocyclic acetates (1a–3a) in good to high enantiomeric excess (88%–92% ee). Whilst, the (S)-heteroaromatic acetates (5a and 6a) are given with moderate enantiomeric excess (51%–62% ee). All the (S)-acetates are given in good isolated chemical yields (>80%) allowing to overcome the maximum of 50% yield which could be usually reached in a regular kinetic resolution processes.

Dynamic Kinetic Resolution of Alcohols by Enantioselective Silylation Enabled by Two Orthogonal Transition-Metal Catalysts

A nonenzymatic dynamic kinetic resolution of acyclic and cyclic benzylic alcohols is reported. The approach merges rapid transition-metal-catalyzed alcohol racemization and enantioselective Cu-H-catalyzed dehydrogenative Si-O coupling of alcohols and hydrosilanes. The catalytic processes are orthogonal, and the racemization catalyst does not promote any background reactions such as the racemization of the silyl ether and its unselective formation. Often-used ruthenium half-sandwich complexes are not suitable but a bifunctional ruthenium pincer complex perfectly fulfills this purpose. By this, enantioselective silylation of racemic alcohol mixtures is achieved in high yields and with good levels of enantioselection.

Mechanochemical, Water-Assisted Asymmetric Transfer Hydrogenation of Ketones Using Ruthenium Catalyst

Asymmetric catalytic reactions are among the most convenient and environmentally benign methods to obtain optically pure compounds. The aim of this study was to develop a green system for the asymmetric transfer hydrogenation of ketones, applying chiral Ru catalyst in aqueous media and mechanochemical energy transmission. Using a ball mill we have optimized the milling parameters in the transfer hydrogenation of acetophenone followed by reduction of various substituted derivatives. The scope of the method was extended to carbo- and heterocyclic ketones. The scale-up of the developed system was successful, the optically enriched alcohols could be obtained in high yields. The developed mechanochemical system provides TOFs up to 168 h?1. Our present study is the first in which mechanochemically activated enantioselective transfer hydrogenations were carried out, thus, may be a useful guide for the practical synthesis of optically pure chiral secondary alcohols.

Chitosan as a chiral ligand and organocatalyst: Preparation conditions-property-catalytic performance relationships

Chitosan is an abundant and renewable chirality source of natural origin. The effect of the preparation conditions by alkaline hydrolysis of chitin on the properties of chitosan was studied. The materials obtained were used as ligands in the ruthenium-catalysed asymmetric transfer hydrogenation of aromatic prochiral ketones and oxidative kinetic resolution of benzylic alcohols as well as organocatalysts in the Michael addition of isobutyraldehyde to N-substituted maleimides. The degrees of deacetylation of the prepared materials were determined by 1H NMR, FT-IR and UV-vis spectroscopy, the molecular weights by viscosity measurements, their crystallinity by WAXRD, and their morphology by SEM and TEM investigations. The materials were also characterized by Raman spectroscopy. The biopolymers which have molecular weights in a narrow (200-230 kDa) range and appropriate (80-95%) degrees of deacetylation were the most efficient ligands in the enantioselective transfer hydrogenation, whereas in the oxidative kinetic resolution the activity of the complexes and the stereoselectivity increased with the degree of deacetylation. The chirality of the chitosan was sufficient to obtain enantioselection in the Michael addition of isobutyraldehyde to maleimides in the aqueous phase. Interestingly, the biopolymer afforded the opposite enantiomer in excess compared to the monomer, d-glucosamine. In this reaction, good correlation between the degree of deacetylation and the catalytic activity was found. These results are novel steps in the application of this natural, biocompatible and biodegradable polymer in developing environmentally benign methods for the production of optically pure fine chemicals.

Chiral amino-pyridine-phosphine tridentate ligand, manganese complex, and preparation method and application thereof

The invention discloses a chiral amino-pyridine-phosphine tridentate ligand, a manganese complex, and a preparation method and application thereof. The chiral amino-pyridine-phosphine tridentate ligand is shown as a formula II, and the manganese complex of the chiral amino-pyridine-phosphine tridentate ligand can be used for efficiently catalyzing and hydrogenating ketone compounds to prepare chiral alcohol compounds in a high enantioselectivity mode. The chiral amino-pyridine-phosphine tridentate ligand and the manganese complex are simple in synthesis process, good in stability, high in catalytic activity and mild in reaction conditions.

Highly Enantioselective Transfer Hydrogenation of Prochiral Ketones Using Ru(II)-Chitosan Catalyst in Aqueous Media

Unprecedentedly high enantioselectivities are obtained in the transfer hydrogenation of prochiral ketones catalyzed by a Ru complex formed in situ with chitosan chiral ligand. This biocompatible, biodegradable chiral polymer obtained from the natural chitin afforded good, up to 86 % enantioselectivities, in the aqueous-phase transfer hydrogenation of acetophenone derivatives using HCOONa as hydrogen donor. Cyclic ketones were transformed in even higher, over 90 %, enantioselectivities, whereas further increase, up to 97 %, was obtained in the transfer hydrogenations of heterocyclic ketones. The chiral catalyst precursor prepared ex situ was examined by scanning electron microscopy, FT-mid- and -far-IR spectroscopy. The structure of the in situ formed catalyst was investigated by 1H NMR spectroscopy and using various chitosan derivatives. It was shown that a Ru pre-catalyst is formed by coordination of the biopolymer to the metal by amino groups. This precursor is transformed in water insoluble Ru-hydride complex following hydrogen donor addition. The practical value of the developed method was verified by preparing over twenty chiral alcohols in good yields and optical purities. The catalyst was applied for obtaining optically pure chiral alcohols at gram scale following a single crystallization.

Ruthenium(II)-Chitosan, an Enantioselective Catalyst for the Transfer Hydrogenation of N-Heterocyclic Ketones

The present study aimed at extending the applicability of a recently developed stereoselective catalytic system to the preparation of optically enriched N-heterocyclic alcohols. Chiral ruthenium catalyst formed in situ using the chitosan biopolymer as ligand, which provided good results in the transfer hydrogenation of heterobicyclic compounds, such as 4-chromanone and 4-thiochromanone, was used in reactions of various N-containing prochiral ketones. High enantioselectivities were reached in transfer hydrogenations of bicyclic compounds bearing nitrogen either in aromatic or cycloaliphatic moieties, provided that the amino group was protected or shielded by a nearby substituent. Results were rationalized by interactions of the nitrogen with the metal and/or ligand. N-containing bicyclic compounds having heteroatoms in both rings were also prepared and tested. The detrimental effect of the pyridyl moiety was compensated by the beneficial influence of the heteroatom in the cycloaliphatic ring, as indicated by high rates and good enantioselectivities obtained in reactions of these compounds. Preparation of several N-heterocyclic alcohols, in good yields and high optical purities was achieved using Ru(II)-chitosan complex.

Enantioselective Hydrogenation of Ketones using Different Metal Complexes with a Chiral PNP Pincer Ligand

The synthesis of different metal pincer complexes coordinating to the chiral PNP ligand bis(2-((2R,5R)-2,5-dimethyl-phospholanoethyl))amine is described in detail. The characterized complexes with Mn, Fe, Re and Ru as metal centers showed good activities regarding the reduction of several prochiral ketones. Comparing these catalysts, the non-noble metal complexes produced best selectivities not only for aromatic substrates, but also for different kinds of aliphatic ones leading to enantioselectivities up to 99% ee. Theoretical investigations elucidated the mechanism and rationalized the selectivity. (Figure presented.).

CHIRAL METAL COMPLEX COMPOUNDS

The invention comprises novel chiral metal complex compounds of the formula (I) wherein M, PR2, R3 and R4 are outlined in the description, its stereoisomers, in the form as a neutral complex or a complex cation with a suitable counter ion. The chiral metal complex compounds can be used in asymmetric reactions, particularly in asymmetric reductions of ketones, imines or oximes.