66838-42-4

Basic information

• Product Name: (R)-Tetrahydro-3-furancarboxylic acid
• Synonyms: (R)-Tetrahydro-3-furancarboxylic acid;(R)-Tetrahydrofuran-3-carboxylic acid;(R)-Tetrahydrofuran-3-car...;(R)-Tetrahydro-3-furoic acid;(3R)-oxolane-3-carboxylic acid;3-Furancarboxylic acid, tetrahydro-, (3R)-;(R)-Tetrahydro-3-furoic acid >=97.0%;(3R)-Tetrahydrofuran-3-carboxylic acid
• CAS NO: 66838-42-4
• Molecular Formula: C₅H₈O₃
• Molecular Weight: 116.11522
• Product Categories: Heterocycle-other series
• Mol File: 66838-42-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 252.1°C at 760 mmHg
• Flash Point: 113.2°C
• Appearance: /
• Density: 1.262g/cm³
• Vapor Pressure: 0.00618mmHg at 25°C
• Refractive Index: 1.48
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.33±0.20(Predicted)
• BRN: 1281202
• CAS DataBase Reference: (R)-Tetrahydro-3-furancarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-Tetrahydro-3-furancarboxylic acid(66838-42-4)
• EPA Substance Registry System: (R)-Tetrahydro-3-furancarboxylic acid(66838-42-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 66838-42-4(Hazardous Substances Data)

Usage

Description

(R)-Tetrahydro-3-furancarboxylic acid, also known as (R)-THFCA, is a chiral organic compound belonging to the tetrahydrofuran carboxylic acid family. It is characterized by its unique (R)-configuration, which is crucial for its biological activity and potential applications. (R)-Tetrahydro-3-furancarboxylic acid exhibits a distinctive chemical structure, featuring a tetrahydrofuran ring fused with a carboxylic acid group, which endows it with specific properties and reactivity.

Uses

Used in Pharmaceutical Industry:
(R)-Tetrahydro-3-furancarboxylic acid is used as a key intermediate in the synthesis of various pharmaceutical compounds, particularly for the preparation of zeste enhancer homolog 2 (EZH2) inhibitors. These inhibitors are of significant interest due to their potential role in the treatment of various cancers by targeting the epigenetic regulation of gene expression.
(R)-Tetrahydro-3-furancarboxylic acid is used as a building block for the development of EZH2 inhibitors, which are designed to modulate the activity of the EZH2 enzyme. This enzyme is a component of the polycomb repressive complex 2 (PRC2), which is involved in the regulation of gene expression by catalyzing the methylation of histone H3 at lysine 27 (H3K27me3). Dysregulation of EZH2 has been implicated in various cancers, making it an attractive target for therapeutic intervention.
In the context of cancer treatment, (R)-Tetrahydro-3-furancarboxylic acid is used as a precursor for the synthesis of EZH2 inhibitors that can potentially suppress tumor growth and progression by re-establishing the normal epigenetic landscape. These inhibitors may also enhance the effectiveness of conventional chemotherapy and radiotherapy, offering a promising avenue for combination therapies in oncology.
Furthermore, (R)-Tetrahydro-3-furancarboxylic acid may also find applications in other therapeutic areas, given its unique chemical properties and potential for further chemical modifications. Its chiral nature and reactivity make it a valuable component in the design and synthesis of novel drugs and drug candidates, with potential applications in various medical fields.

InChI:InChI=1/C5H8O3/c6-5(7)4-1-2-8-3-4/h4H,1-3H2,(H,6,7)/t4-/m1/s1

Upstream product

• 130193-89-4 (R)-tetrahydro-furan-3-carboxylic acid benzyl ester 
• 1445651-64-8 tetrahydro-furan-3-carboxylic acid benzyl ester 
• 89364-31-8 3-tetrahydrofuroic acid 
• 797038-34-7 tert-butyl 2,5-dihydrofuran-3-carboxylate 
• 797038-33-6 tert-butyl 4-hydroxytetrahydrofuran-3-carboxylate 
• 1002728-73-5 2,5-dihydrofuran-3-carboxylic acid 
• 191347-92-9 (R)-tetrahydrofuran-3-carboxaldehyde 

Downstream Products

• 165611-33-6 (R)-methyl tetrahydro-3-furoate 
• 124391-75-9 -(+)-3-hydroxymethyltetrahydrofuran 
• 1163126-58-6 4-(2-fluoro-4-(((R)-tetrahydrofuran-3-carbonyl)amino)phenyl)piperazine-1-carboxylic acid tert-butyl ester 
• 1220514-67-9 C₂₇H₃₄FN₅O₃ 
• 1220514-58-8 C₂₇H₃₄FN₅O₃*ClH 

Relevant articles and documents

Dihydro-Benzo-Oxazine and Dihydro-Pyrido-Oxazine Derivatives

The invention relates to dihydro-benzo-oxazine and dihydro-pyrido-oxazine compounds of the formula (I) and/or pharmaceutically acceptable salts and/or solvates thereof, wherein Y, V, W, U, Q, R1, R5, R7 and R30 are as defined in the description. Such compounds are suitable for the treatment of a disorder or disease which is mediated by the activity of the PI3K enzymes.

Asymmetric Hydroformylation of Heterocyclic Olefins Catalyzed by Chiral Phosphine-Phosphite-Rh(I) Complexes

Asymmetric hydroformylation of heterocyclic olefins catalyzed by phosphine-phosphite-Rh(I) complexes has been investigated. Hydroformylation of symmetrical heterocyclic olefins such as 2,5-dihydrofuran, 3-pyrroline derivatives, and 4,7-dihydro-1,3-dioxepin derivatives afforded the optically active aldehydes as single products in 64-76% ee. Unsymmetrical substrates such as 2,3-dihydrofuran and N-(tert-butoxycarbonyl)-2-pyrroline gave a mixture of regioisomers. From N-(tert-butoxycarbonyl)-2-pyrroline was obtained N-(tert-butoxycarbonyl)pyrrolidine-2-carbaldehyde in 97% ee. The hydroformylation products from 2,5-dihydrofuran and N-(tert-butoxycarbonyl)-3-pyrroline have the opposite configurations to those from 2,3-dihydrofuran and N-(tert-butoxycarbonyl)-2-pyrroline, respectively, with the same catalyst. The new phosphine-phosphite ligand (R,S)-3,3′-Me2-BINAPHOS [= (A)-2-(diphenylphosphino)-1,1′-binaphthalen-2′-yl (S)-3,3′-dimethyl-1,1′-binaphthalene-2,2′-diyl phosphite] was prepared and its hydridorhodium complex was characterized by NMR spectroscopy. Using (R,S)-3,3′-Me2-BINAPHOS as a ligand, the enantioselectivity was improved for some substrates. In addition, higher catalytic activity was observed with this ligand for most of the substrates employed.