40456-51-7

Basic information

• Product Name: 2(3H)-Furanone, 4-(1,3-benzodioxol-5-ylmethyl)-3-((3,4-dimethoxyphenyl )methyl)dihydro-, (3R-trans)-
• Synonyms: 2(3H)-Furanone, 4-(1,3-benzodioxol-5-ylmethyl)-3-((3,4-dimethoxyphenyl )methyl)dihydro-, (3R-trans)-;bursehernin;(3R)-3α-(3,4-Dimethoxybenzyl)-4β-[(1,3-benzodioxole-5-yl)methyl]-4,5-dihydrofuran-2(3H)-one;(3R)-3α-(3,4-Dimethoxybenzyl)-4β-[3,4-(methylenedioxy)benzyl]dihydrofuran-2(3H)-one;(3R,4R)-3-(3,4-Dimethoxybenzyl)-4-(1,3-benzodioxole-5-ylmethyl)-4,5-dihydrofuran-2(3H)-one;(3R,4R)-4-[(1,3-Benzodioxole-5-yl)methyl]-4,5-dihydro-3-[(3,4-dimethoxyphenyl)methyl]furan-2(3H)-one;4,5-Dihydro-4β-[(1,3-benzodioxole-5-yl)methyl]-3α-(3,4-dimethoxybenzyl)furan-2(3H)-one
• CAS NO: 40456-51-7
• Molecular Formula: C₂₁H₂₂O₆
• Molecular Weight: 370.4
• Mol File: 40456-51-7.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 543.6°Cat760mmHg
• Flash Point: 238.5°C
• Appearance: /
• Density: 1.268g/cm³
• Vapor Pressure: 7.08E-12mmHg at 25°C
• Refractive Index: 1.586
• CAS DataBase Reference: 2(3H)-Furanone, 4-(1,3-benzodioxol-5-ylmethyl)-3-((3,4-dimethoxyphenyl )methyl)dihydro-, (3R-trans)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(3H)-Furanone, 4-(1,3-benzodioxol-5-ylmethyl)-3-((3,4-dimethoxyphenyl )methyl)dihydro-, (3R-trans)-(40456-51-7)
• EPA Substance Registry System: 2(3H)-Furanone, 4-(1,3-benzodioxol-5-ylmethyl)-3-((3,4-dimethoxyphenyl )methyl)dihydro-, (3R-trans)-(40456-51-7)

Safety Data

• Hazardous Substances Data: 40456-51-7(Hazardous Substances Data)

Usage

Furanone ring

A three-membered ring with an oxygen atom and a double bond between two of the members.

Benzodioxol moiety

A benzene ring with two oxygen atoms attached in a 1,3-dioxole configuration.

Cis-configuration

The spatial arrangement of the substituents on the furanone ring is on the same side.

Trans-configuration

The spatial arrangement of the substituents on the carbon atom on the furanone ring is on opposite sides.

Three aromatic rings

The compound has three benzene rings, which are characterized by their stability and aromaticity.

Two methoxy-substituted rings

Two of the aromatic rings are substituted with methoxy groups (-OCH3), which are electron-donating and can influence the chemical properties of the compound.

One phenylmethyl-substituted ring

One of the aromatic rings is substituted with a phenylmethyl group (-CH2C6H5), which can provide steric hindrance and affect the reactivity of the compound.

Dihydro compound

The compound has a saturated ring, meaning that it has two hydrogen atoms attached to each carbon atom in the ring.

Potential applications

The unique structure and properties of this chemical may make it useful in pharmaceuticals, fragrances, or as a flavoring agent.

InChI:InChI=1/C21H22O6/c1-23-17-5-3-14(9-19(17)24-2)8-16-15(11-25-21(16)22)7-13-4-6-18-20(10-13)27-12-26-18/h3-6,9-10,15-16H,7-8,11-12H2,1-2H3/t15-,16+/m0/s1

Upstream product

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• 17187-77-8 (R)-(+)-3-piperonyl-4-butanolide 
• 30830-55-8 3-(3,4-methylenedioxyphenyl)propionaldehyde 
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• 139501-40-9 (+/-) 1-(3,4-dimethoxyphenyl)-4-(3,4-methylenedioxyphenyl) butane 
• 120-57-0 piperonal 
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• 139501-44-3 (+/-) 1-(3,4-dimethoxyphenyl)-4-(3,4-methylenedioxyphenyl)-butane 2,3-dicarboxylic acid 
• 86926-69-4 (+/-) 1-(3,4-dimethoxyphenyl)-4-(3,4-methylenedioxyphenyl) butane 2,3-dicarboxylic acid dimethyl ester 

Relevant articles and documents

Intermolecular oxidative enolate heterocoupling

(Chemical Equation Presented) No priming necessary: The intermolecular oxidative heterocoupling of imides and oxindoles to esters, ketones, and lactones is shown for the first time to be synthetically viable. Strategic use of the initial oxidation state o

Modular synthesis and biological investigation of 5-hydroxymethyl dibenzyl butyrolactones and related lignans

Dibenzyl butyrolactone lignans are well known for their excellent biological properties, particularly for their notable anti-proliferative activities. Herein we report a novel, efficient, convergent synthesis of dibenzyl butyrolactone lignans utilizing the acyl-Claisen rearrangement to stereoselectively prepare a key intermediate. The reported synthetic route enables the modification of these lignans to give rise to 5-hydroxymethyl derivatives of these lignans. The biological activities of these analogues were assessed, with derivatives showing an excellent cytotoxic profile which resulted in programmed cell death of Jurkat T-leukemia cells with less than 2% of the incubated cells entering a necrotic cell death pathway.

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.