27948-61-4

Basic information

• Product Name: (R)-(+)-1-(2-FURYL)ETHANOL
• Synonyms: R(+)-2-FURYL METHYL CARBINOL;(R)-(+)-ALPHA-METHYLFURAN-2-METHANOL;(R)-(+)-1-(2-FURYL)ETHANOL;(R)-1-(2-FURYL)ETHANOL;(R)-(+)-1-(2-FURYL)ETHANOL 98%;(R)-(+)-(2-Furyl)ethanol;(r)-(+)-α-methylfuran-2-methanol;(R)-1-(2-Furyl)ethanol(stabilized with hydroquinone)
• CAS NO: 27948-61-4
• Molecular Formula: C₆H₈O₂
• Molecular Weight: 112.13
• Product Categories: Alcohols, Hydroxy Esters and Derivatives;Chiral Compounds
• Mol File: 27948-61-4.mol
• Article Data: 218

Chemical Properties

• Boiling Point: 64-65 °C13 mm Hg(lit.)
• Flash Point: 110 °C
• Appearance: /
• Density: 1.078 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.479
• Storage Temp.: −20°C
• PKA: 14.09±0.20(Predicted)
• CAS DataBase Reference: (R)-(+)-1-(2-FURYL)ETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-1-(2-FURYL)ETHANOL(27948-61-4)
• EPA Substance Registry System: (R)-(+)-1-(2-FURYL)ETHANOL(27948-61-4)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 27948-61-4(Hazardous Substances Data)

Usage

Description

(R)-(+)-1-(2-FURYL)ETHANOL, also known as (R)-1-(Furan-2-yl)ethanol, is a clear light yellow to yellow liquid with unique chemical properties. It is a valuable compound in the field of organic synthesis due to its versatile reactivity and structural features.

Uses

Used in Organic Synthesis:
(R)-(+)-1-(2-FURYL)ETHANOL is used as a key reactant in organic synthesis for the development of various chemical compounds. Its unique structure allows it to participate in a wide range of reactions, making it a valuable building block for creating complex molecules with specific properties and applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (R)-(+)-1-(2-FURYL)ETHANOL is used as an intermediate in the synthesis of pharmaceutical compounds. Its ability to form diverse chemical structures makes it a promising candidate for the development of new drugs with improved efficacy and reduced side effects.
Used in Flavor and Fragrance Industry:
(R)-(+)-1-(2-FURYL)ETHANOL is also utilized in the flavor and fragrance industry as a component in the creation of various scents and flavors. Its distinct chemical properties contribute to the development of unique and appealing sensory experiences.
Used in Material Science:
In the field of material science, (R)-(+)-1-(2-FURYL)ETHANOL is employed as a component in the development of advanced materials with specific properties. Its versatility in chemical reactions allows for the creation of materials with tailored characteristics for various applications, such as electronics, coatings, and adhesives.
Overall, (R)-(+)-1-(2-FURYL)ETHANOL is a versatile and valuable compound with a wide range of applications across different industries, including organic synthesis, pharmaceuticals, flavor and fragrance, and material science. Its unique chemical properties and reactivity make it an essential component in the development of new and innovative products.

Upstream product

• 98-01-1 furfural 
• 544-97-8 dimethyl zinc(II) 
• 75-16-1 methylmagnesium bromide 
• 74-88-4 methyl iodide 
• 4208-64-4 1-(2-furyl)ethanol 
• 1192-62-7 1-(2-furyl)-1-ethanone 
• 113531-28-5 Octanoic acid 1-furan-2-yl-ethyl ester 
• 1487-18-9 (furan-2-yl)ethylene 
• 108-22-5 Isopropenyl acetate 
• 209682-89-3 1-ethoxyvinyl methyl fumarate 
• 638-11-9 isopropyl butyrate 
• 101-41-7 benzeneacetic acid methyl ester 
• 108-05-4 vinyl acetate 
• 117-34-0 2,2-diphenylacetic acid 

Downstream Products

• 33647-67-5 (S)-1-(2,5-dihydro-2,5-dimethoxy-2-furyl)ethanol 
• 113471-32-2 (R)-1-(furan-2-yl)ethyl acetate 
• 201279-57-4 (S)-benzoic acid 1-furan-2-yl-ethyl ester 
• 201279-54-1 (R)-(+)-2-(1-benzoyloxyethyl)furan 
• 266323-47-1 (S)-1-(2-furyl)-1-(4-methoxybenzyloxy)ethane 
• 862902-41-8 exo,exo-(1S)-1-((1R)-1-benzoyloxyethyl)-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride 
• 735315-15-8 Kaempferol-3-O-(2,3,4-tri-O-acetyl-alpha-L-rhamnopyranoside) 
• 910041-19-9 (2S,3R,4R,5S,6S)-2-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 916069-02-8 3-((2S,6S)-5,6-dihydro-6-methyl-5-oxo-2H-pyran-2-yloxy)-5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4H-chromen-4-one 
• 916069-03-9 3-((2S,5R,6S)-5,6-dihydro-5-hydroxy-6-methyl-2H-pyran-2-yloxy)-5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4H-chromen-4-one 
• 916069-05-1 6-(5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yloxy)-3,6-dihydro-2-methyl-2H-pyran-3-yl acetate 
• 916069-04-0 5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one 
• 916069-06-2 (2S,3R,4S,5R,6S)-6-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-4,5-dihydroxy-2-methyltetrahydro-2H-pyran-3-yl acetate 
• 916069-07-3 (2S,3R,4R,5R,6S)-2-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-4-hydroxy-6-methyltetrahydro-2H-pyran-3,5-diyl diacetate 

Relevant articles and documents

A common synthetic route to homochiral tetracycles related to pillaromycinone and premithramycinone

Homochiral AB segments for (+)-and (-)-pillaromycinone were prepared in 11 steps from 2-acetylfuran. The synthesis featured an intramolecular Diels-Alder reaction of a 2,5-disubstituted furan and a hydroxyl-directed homogeneous hydrogenation of the tetrasubstituted alkene double bond of two enones. The CD segment was attached by a modified Staunton-Weinreb annulation to produce the desired homochiral tetracycle 21c related to (+)-pillaromycinone. An unusual acetonide migration enabled the synthesis of a tetracyclic model for premithramycinone.

2, 4, 5-Trideoxyhexopyranosides Derivatives of 4’-Demethylepipodophyllotoxin: De novo Synthesis and Anticancer Activity

Background: Podophyllotoxin is a natural lignan which possesses anticancer and antiviral activities. Etoposide and teniposide are semisynthetic glycoside derivatives of podophyllotoxin and are increasingly used in cancer medicine. Objective: The present work aimed to design and synthesize a series of 2, 4, 5-trideoxyhexopyrano-sides derivatives of 4’-demethylepipodophyllotoxin as novel anticancer agents. Methods: A divergent de novo synthesis of 2, 4, 5-trideoxyhexopyranosides derivatives of 4’-demethylepipodophyllotoxin has been established via palladium-catalyzed glycosylation. The abili-ties of synthesized glycosides to inhibit the growth of A549, HepG2, SH-SY5Y, KB/VCR and HeLa cancer cells were investigated by MTT assay. Flow cytometric analysis of cell cycle with propidium iodide DNA staining was employed to observe the effect of compound 5b on cancer cell cycle. Results: Twelve D and L monosaccharide derivatives 5a-5l have been efficiently synthesized in three steps from various pyranone building blocks employing de novo glycosylation strategy. D-monosaccharide 5b showed the highest cytotoxicity on five cancer cell lines with the IC50 values ranging from 0.9 to 6.7 μM. It caused HepG2 cycle arrest at G2/M phase in a concentration-dependent manner. Conclusion: The present work leads to the development of novel 2, 4, 5-trideoxyhexopyranosides derivatives of 4’-demethylepipodophyllotoxin. The biological results suggest that the replacement of the glucosyl moiety of etoposide with 2, 4, 5-trideoxyhexopyranosyl is favorable to their cytotoxic-ity. D-monosaccharide 5b was observed to cause HepG2 cycle arrest at the G2/M phase in a concen-tration-dependent manner.

Cinchona-Alkaloid-Derived NNP Ligand for Iridium-Catalyzed Asymmetric Hydrogenation of Ketones

Most ligands applied for asymmetric hydrogenation are synthesized via multistep reactions with expensive chemical reagents. Herein, a series of novel and easily accessed cinchona-alkaloid-based NNP ligands have been developed in two steps. By combining [Ir(COD)Cl]2, 39 ketones including aromatic, heteroaryl, and alkyl ketones have been hydrogenated, all affording valuable chiral alcohols with 96.0-99.9% ee. A plausible reaction mechanism was discussed by NMR, HRMS, and DFT, and an activating model involving trihydride was verified.

Phase Separation-Promoted Redox Deracemization of Secondary Alcohols over a Supported Dual Catalysts System

Unification of oxidation and reduction in a one-pot deracemization process has great significance in the preparation of enantioenriched organic molecules. However, the intrinsic mutual deactivation of oxidative and reductive catalysts and the extrinsic incompatible reaction conditions are unavoidable challenges in a single operation. To address these two issues, we develop a supported dual catalysts system to overcome these conflicts from incompatibility to compatibility, resulting in an efficient one-pot redox deracemization of secondary alcohols. During this transformation, the TEMPO species onto the outer surface of silica nanoparticles catalyze the oxidation of racemic alcohols to ketones, and the chiral Rh/diamine species in the nanochannels of the thermoresponsive polymer-coated hollow-shell mesoporous silica enable the asymmetric transfer hydrogenation (ATH) of ketones to chiral alcohols. To demonstrate the general feasibility, a series of orthogonal oxidation/ATH cascade reactions are compared to prove the compatible benefits in the elimination of their deactivations and the balance of the cascade directionality. As presented in this study, this redox deracemization process provides various chiral alcohols with enhanced yields and enantioselectivities relative to those from unsupported dual catalysts systems. Furthermore, the dual catalysts can be recycled continuously, making them an attractive feature in the application.