40456-51-7

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

• 78473-72-0 3-(3,4-dimethoxybenzyl)-4-<3,4-methylenedioxy-α,α-bis(phenylthio)behzyl>butyrolactone 
• 78473-66-2 C₂₀H₁₅O₂S₂^(1-) 
• 1432494-09-1 (E)-ethyl 4-(3',4'-dimethoxyphenyl)but-2-enoate 
• 5703-21-9 3,4-dimethoxyphenylacetaldehyde 
• 54844-36-9 3-(3,4-dimethoxyphenyl)propane-1,2-diol 
• 68996-81-6 3-benzo[1,3]dioxol-5-yl-propionyl chloride 
• 2815-95-4 3-(1,3 benzodioxol-5-yl)propionic acid 
• 93-15-2 1,2-dimethoxy-4-(2-propenyl)benzene 
• 7116-48-5 3-benzo[1,3]dioxol-5-yl-propionic acid ethyl ester 
• 24393-66-6 ethyl (E)-3-(benzo[d][1,3]dioxol-5-yl)acrylate 
• 166884-72-6 1-(1-(allyloxy)-2-iodoethoxy)butane 
• 1357013-37-6 3,4-methylenedioxyphenylzinc iodide 
• 80483-34-7 4-(1,3-benzodioxol-5-ylmethyl)-4,5-dihydrofuran-2(3H)-one 
• 21852-32-4 4-bromomethyl-1,2-dimethoxybenzene 

Relevant academic research and scientific papers

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

Asymmetric Chemoenzymatic Synthesis of (?)-Podophyllotoxin and Related Aryltetralin Lignans

(?)-Podophyllotoxin is one of the most potent microtubule depolymerizing agents and has served as an important lead compound in antineoplastic drug discovery. Reported here is a short chemoenzymatic total synthesis of (?)-podophyllotoxin and related aryltetralin lignans. Vital to this approach is the use of an enzymatic oxidative C?C coupling reaction to construct the tetracyclic core of the natural product in a diastereoselective fashion. This strategy allows gram-scale access to (?)-deoxypodophyllotoxin and is readily adaptable to the preparation of related aryltetralin lignans.

Ni-Catalyzed Regioselective Dicarbofunctionalization of Unactivated Olefins by Tandem Cyclization/Cross-Coupling and Application to the Concise Synthesis of Lignan Natural Products

We disclose a (terpy)NiBr2-catalyzed reaction protocol that regioselectively difunctionalizes unactivated olefins with tethered alkyl halides and arylzinc reagents. The reaction shows an excellent functional group tolerance (such as ketones, es

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.

Trypanocidal structure-activity relationship for cis- and trans-methylpluviatolide

The trypanocidal activity of racemic mixtures of cis- and trans-methylpluviatolides was evaluated in vitro against trypomastigote forms of two strains of Trypanosoma cruzi, and in the enzymatic assay of T. cruzi gGAPDH. The cytotoxicity of the compounds w

Intermolecular enolate heterocoupling: Scope, mechanism, and application

This full account presents the background on, discovery of, and extensive insight that has been gained into the oxidative intermolecular coupling of two different carbonyl species. Optimization of this process has culminated in reliable and scalable proto

PROCESS TO OBTAIN SYNTHETIC AND SEMI-SYNTHETIC LIGNAN DERIVATIVES, THEIR ANTIPARASITIC ACTIVITIES AND CORRESPONDING PHARMACEUTICAL FORMULATIONS, INCLUDING THE THERAPEUTIC METHOD USING SAID LIGNAN FOR THE TREATMENT OF PARASITOSIS

The invention refers to a process to obtain synthetic and semi-synthetic derivatives of lignans, especially dibenzylbutyrolactonic, tetrahydrofuranic, aryltetralynic, furofuranic and dibenzocyclooctanic lignans obtained by means of partial synthesis and/o

Isolation, structure and synthesis of new diarylbutane lignans from Phyllanthus niruri: Synthesis of 5'-desmethoxy niranthin and an antitumour extractive

The structures of three new lignans (1-3) and a phenolic lignan (4) isolated from Phyllanthus niruri have been determined. The structures (1-3) were confirmed by their total synthesis and that of (4) was by its conversion to (3). The synthesis of (±) 5'-d

Isokaerophyllin, a butyrolactone from Bupleurum salicifolium

From the leaves of Bupleurum salicifolium two benzylidene-benzyl-γ-butyrolactone-type lignans were isolated. One was identified as kaerophyllin, the other as its cis-isomer, hitherto unreported. The latter was characterized as 2(3,4-dimethoxy)-benzylidene