58311-20-9

Basic information

• Product Name: (3R,4R)-3-[(1,3-Benzodioxole-5-yl)methyl]-4-(3,4-dimethoxybenzyl)-4,5-dihydrofuran-2(3H)-one
• Synonyms: (-)-Kusunokinin;(3R,4R)-3-[(1,3-Benzodioxole-5-yl)methyl]-4-(3,4-dimethoxybenzyl)-4,5-dihydrofuran-2(3H)-one;[3R,(-)]-3α-(1,3-Benzodioxole-5-ylmethyl)-4β-(3,4-dimethoxybenzyl)-4,5-dihydrofuran-2(3H)-one;(3R,4R)-3-(1,3-Benzodioxol-5-ylmethyl)-4-[(3,4-dimethoxyphenyl)methyl]dihydro-2(3H)-furanone
• CAS NO: 58311-20-9
• Molecular Formula: C₂₁H₂₂O₆
• Molecular Weight: 370.39578
• Mol File: 58311-20-9.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3R,4R)-3-[(1,3-Benzodioxole-5-yl)methyl]-4-(3,4-dimethoxybenzyl)-4,5-dihydrofuran-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4R)-3-[(1,3-Benzodioxole-5-yl)methyl]-4-(3,4-dimethoxybenzyl)-4,5-dihydrofuran-2(3H)-one(58311-20-9)
• EPA Substance Registry System: (3R,4R)-3-[(1,3-Benzodioxole-5-yl)methyl]-4-(3,4-dimethoxybenzyl)-4,5-dihydrofuran-2(3H)-one(58311-20-9)

Safety Data

• Hazardous Substances Data: 58311-20-9(Hazardous Substances Data)

Usage

General Description

The chemical (3R,4R)-3-[(1,3-Benzodioxole-5-yl)methyl]-4-(3,4-dimethoxybenzyl)-4,5-dihydrofuran-2(3H)-one is a complex organic compound with a molecular structure containing a furan ring and various aromatic moieties. It is classified as a heterocyclic compound and has potential applications in pharmaceutical and medicinal chemistry due to its diverse structural features. The presence of benzodioxole and dimethoxybenzyl groups suggests potential biological activity, and further research may reveal its potential as a drug candidate or lead compound for the development of new therapeutic agents. Additionally, its unique structure and functional groups make it a valuable target for organic synthesis and chemical research.

Upstream product

• 2606-51-1 3,4-Methylenedioxybenzyl bromide 
• 108102-77-8 (R)-4-(3,4-dimethoxybenzyl)dihydrofuran-2(3H)-one 
• 140138-38-1 (3R,4R,5R)-3-Benzo[1,3]dioxol-5-ylmethyl-4-(3,4-dimethoxy-benzyl)-5-(2-isopropyl-5-methyl-cyclohexyloxy)-dihydro-furan-2-one 
• 140138-38-1 (-)-(3S,4R,5R)-3-(3',4'-methylenedioxybenzyl)-4-(3'',4''-dimethoxybenzyl)-5-(1-menthyloxy)butyrolactone 
• 60354-22-5 4-[Bis(phenylsulfanyl)methyl]-1,2-dimethoxybenzene 
• 157766-09-1 5-(iodomethyl)benzo[d][1,3]dioxole 
• 140138-36-9 (-)-(3S,4R,5R)-3-(3',4'-methylenedioxybenzyl)-4-<3'',4''-dimethoxy-α,α-bis(phenylthio)benzyl>-5-(1-menthyloxy)butyrolactone 
• 108102-79-0 (R)-(+)-α-(dimethoxy-3,4 benzyl)hemisuccinate de methyle 
• 78647-52-6 (+/-)-4-(3,4-dimethoxyphenyl)-3-methoxycarbonylbutanoic acid 
• 140138-36-9 (3R,4R,5R)-3-Benzo[1,3]dioxol-5-ylmethyl-4-[(3,4-dimethoxy-phenyl)-bis-phenylsulfanyl-methyl]-5-(2-isopropyl-5-methyl-cyclohexyloxy)-dihydro-furan-2-one 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 72430-92-3 4-[(3,4-dimethoxyphenyl)methyl]dihydrofuran-2-one 
• 72622-61-8 α-(trans-3',4'-methylenedioxybenzylidene)-β-(3,4-dimethoxybenzyl)-γ-butyrolactone 
• 78647-51-5 4-[3,4-dimethoxyphenyl]-3-(methoxycarbonyl)-3-butenoic acid 

Downstream Products

• 67533-86-2 (-)-dimethoxy-3',4' desmethylenedioxy-3',4' cubebine 
• 131318-42-8 (3S^*,4R^*)-3-ethyl-3-<3,4-(methylenedioxy)benzyl>-4-(3,4-dimethoxybenzyl)-γ-butyrolactone 
• 131318-42-8 (3R^*,4R^*)-3-ethyl-3-<3,4-(methylenedioxy)benzyl>-4-(3,4-dimethoxybenzyl)-γ-butyrolactone 
• 131318-40-6 (3S^*,4R^*)-3-methyl-3-<3,4-(methylenedioxy)benzyl>-4-(3,4-dimethoxybenzyl)-γ-butyrolactone 
• 131318-40-6 (3R^*,4R^*)-3-methyl-3-<3,4-(methylenedioxy)benzyl>-4-(3,4-dimethoxybenzyl)-γ-butyrolactone 

Relevant articles and documents

Discovery of stereospecific cytotoxicity of (8R,8′R)-trans-arctigenin against insect cells and structure-activity relationship on aromatic ring

One of the arctigenin stereoisomers, (8R,8′R)-trans-form 1, showed stereospecific cytotoxicity against insect cells, Sf9 and NIAS-AeAl-2 cells. By the comparison with other stereoisomers, the most importance of the 8′R stereochemistry for the higher activities was clarified. On the other hand, the wider range of activity level among stereoisomers against cancer cells, HL-60, was not observed. The structure-activity relationship research using derivatives bearing (8R,8′R)-trans-form was performed to show the same level of activities of 3-iodo, 4-iodo, and 3,4-methylenedioxy derivatives 28, 29, and 36 as (8R,8′R)-trans-arctigenin 1. In the examination of thiono derivatives, 4-iodo thiono and 3,4-methylenedioxy thiono derivatives 66, 67 showed similar level of activities to that of (8R,8′R)-trans-arctigenin 1. The expression of ribosomal 28S rRNA gene of Sf9 cells was increased by (8R,8′R)-trans-arctigenin 1, whereas a degradation of DNA was not observed.

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.

Simple synthesis of trans-α,β-dibenzyl-γ-butyrolactone lignans by diastereoselective reduction of α-benzylidene-β-benzyl-γ-butyralactones using NaBH4-NiCl2

trans-α,β-Dibenzyl-γ-butyrolactone lignans were synthesized by stereoselective reduction of α-benzylidene-β-benzyl-γ-butyrolactones using NaBH4-NiCl2. The reduction is found to proceed via conjugate addition of a hydride to an α-benz