126434-64-8

Basic information

• Product Name: 2(3H)-Furanone, dihydro-4-(phenylmethyl)-, (4R)-
• CAS NO: 126434-64-8
• Molecular Formula: C11H12O2
• Molecular Weight: 176.215
• Mol File: 126434-64-8.mol
• Article Data: 19

Chemical Properties

• CAS DataBase Reference: 2(3H)-Furanone, dihydro-4-(phenylmethyl)-, (4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(3H)-Furanone, dihydro-4-(phenylmethyl)-, (4R)-(126434-64-8)
• EPA Substance Registry System: 2(3H)-Furanone, dihydro-4-(phenylmethyl)-, (4R)-(126434-64-8)

Safety Data

• Hazardous Substances Data: 126434-64-8(Hazardous Substances Data)

Usage

Structure

Dihydrofuranone derivative with a phenylmethyl substituent

Chirality

Chiral molecule with a specific 4R stereochemistry

Biological activities

Potential antimicrobial and antifungal properties

Synthesis

Used in the synthesis of various pharmaceuticals and organic compounds

Importance

Unique structure and potential applications make it an important compound in organic chemistry and pharmaceutical research

Upstream product

• 100-52-7 benzaldehyde 
• 19544-43-5 3-benzyldihydrofuran-2,5-dione 
• 171007-71-9 3-phenyl-1-propyl diazoacetate 
• 55262-02-7 3-benzyl-cyclobutanone 
• 104-53-0 3-phenyl-propionaldehyde 
• 61433-91-8 bromoacetic acid 2,2,2-trifluoroethyl ester 
• 1415610-21-7 4-phenyl-3-methylidenebutanoic acid tert-butyl ester 
• 60468-22-6 2-bromo-3-phenyl-propene 
• 100-58-3 phenylmagnesium bromide 
• 99267-71-7 O,O'-trans-cinnamylidene-L_g-tartaric acid diethyl ester 
• 133269-17-7 (1R,3S,4S,6R)-6-Benzyl-3-methyl-2,7-dioxa-bicyclo[2.2.1]heptane 
• 75332-40-0 C₂₇H₂₈O₈S₂ 
• 133179-00-7 [(4S,5S)-5-Hydroxymethyl-2-((E)-styryl)-[1,3]dioxolan-4-yl]-methanol 
• 133179-02-9 (4R,5R)-4,5-Bis-bromomethyl-2-((E)-styryl)-[1,3]dioxolane 

Relevant articles and documents

Method for preparing 4-chiral substituted gamma-butyrolactone

The invention discloses a method for preparing 4-chiral substituted gamma-butyrolactone. The method comprises the following steps: (a) performing chiral reduction on substituted succinic anhydride serving as a raw material to obtain a compound 2; (b) preparing a corresponding compound 3 from the compound 2 by a reaction of transforming hydroxyl into amino; (c) performing chiral resolution on the compound 3 through chiral solution acids to obtain a compound 4; and (d) performing a deamination reaction on the compound 4 to obtain a final product compound 5. The substituent group R is selected from C1-C8 straight-chain or branched alkyl, 3-8 component alicyclic group, aryl, heteroaryl, Ar(CH2)n-radical, wherein Ar represents aryl and heteroaryl, and n equals to 1-6. The invention provides a novel synthesizing route, raw materials are easily available, and conventional substituted succinic anhydride has bulk production; the operation steps are conventional chemical reactions, are simple and easy and have strong operability; and a final product has good chiral selectivity, has an ee value of between 85-99.5 percent, and has high purity.

Enantioselective α-Alkylation of Aldehydes by Photoredox Organocatalysis: Rapid Access to Pharmacophore Fragments from β-Cyanoaldehydes

The combination of photoredox catalysis and enamine catalysis has enabled the development of an enantioselective α-cyanoalkylation of aldehydes. This synergistic catalysis protocol allows for the coupling of two highly versatile yet orthogonal functionalities, allowing rapid diversification of the oxonitrile products to a wide array of medicinally relevant derivatives and heterocycles. This methodology has also been applied to the total synthesis of the lignan natural product (-)-bursehernin. A combination of photoredox catalysis and enamine catalysis has enabled the development of an enantioselective cyanoalkylation of aldehydes. This synergistic catalysis protocol makes possible the coupling of two highly versatile yet orthogonal functionalities.

Type II flavin-containing monooxygenases: A new class of biocatalysts that harbors baeyer-villiger monooxygenases with a relaxed coenzyme specificity

Within a newly identified set of flavin-containing monooxygenases (FMOs) from Rhodococcus jostii RHA1, we have identified three monooxygenases (FMO-E, FMO-F, and FMO-G) that are effective in catalyzing Baeyer-Villiger oxidations. These type II FMOs display relaxed coenzyme specificity by accepting both NADPH (reduced form of nicotinamide adenine dinucleotide phosphate) and NADH (reduced form of nicotinamide adenine dinucleotide), as a coenzyme, which is a novel and attractive feature among biocatalysts capable of conducting Baeyer-Villiger oxidations. We purified FMO-E and determined that the Michaelis constants for both coenzymes were in the micromolar range, whereas the activity was highest for NADH. By using the stopped-flow technique, formation of a peroxyflavin-enzyme intermediate was observed, which indicated that type II FMOs follow a catalytic mechanism similar to that of other class B flavoprotein monooxygenases. A set of cyclobutanones and cyclohexanones were used to probe the regio- and enantioselectivity of all three recombinant monooxygenases. The biocatalysts readily accepted small cyclic ketones, which enabled the conversion of previously poorly accepted substrates by other monooxygenases (especially norcamphor), and exhibited excellent and unique regio- and enantioselectivities. Sequence analysis revealed that type II FMOs that act as Baeyer-Villiger monooxygenases contain a unique N-terminal domain. Sequence conservation in this protein domain can be used to identify new NADH-dependent Baeyer-Villiger monooxygenases, which would facilitate future biocatalyst discovery efforts. New kid on the block: Members of a newly recognized group of sequence-related flavin-containing monooxygenases can perform Baeyer-Villiger oxidations. Their coenzyme indifference and unique specificity make them attractive biocatalysts.