4892-34-6

Basic information

• Product Name: (5S)-5-(3,4-Dimethoxyphenyl)-5,6,7,8-tetrahydro-6β,7α-dimethylnaphtho[2,3-d]-1,3-dioxole
• Synonyms: (5S)-5-(3,4-Dimethoxyphenyl)-5,6,7,8-tetrahydro-6β,7α-dimethylnaphtho[2,3-d]-1,3-dioxole;Galcatin
• CAS NO: 4892-34-6
• Molecular Formula: C₂₁H₂₄O₄
• Molecular Weight: 340.41286
• Mol File: 4892-34-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 117-118 °C(Solv: methanol (67-56-1))
• Boiling Point: 444.3±45.0 °C(Predicted)
• Appearance: /
• Density: 1.136±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (5S)-5-(3,4-Dimethoxyphenyl)-5,6,7,8-tetrahydro-6β,7α-dimethylnaphtho[2,3-d]-1,3-dioxole(CAS DataBase Reference)
• NIST Chemistry Reference: (5S)-5-(3,4-Dimethoxyphenyl)-5,6,7,8-tetrahydro-6β,7α-dimethylnaphtho[2,3-d]-1,3-dioxole(4892-34-6)
• EPA Substance Registry System: (5S)-5-(3,4-Dimethoxyphenyl)-5,6,7,8-tetrahydro-6β,7α-dimethylnaphtho[2,3-d]-1,3-dioxole(4892-34-6)

Safety Data

• Hazardous Substances Data: 4892-34-6(Hazardous Substances Data)

Upstream product

• 78869-00-8 (7'R,8'S)-7'-(3',4'-dimethoxyphenyl)-8,8'-dimethyl-7',8'-dihydronaphtho[4,5-d][1,3]dioxole 
• 1595276-32-6 5-((1R,2S)-1-(3,4-dimethoxyphenyl)-2-(2-methoxycyclopropyl)propyl)benzo[d][1,3]dioxole 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 77516-01-9 (2S,3R)-3-(2-Benzo[1,3]dioxol-5-yl-[1,3]dithian-2-yl)-2-[(R)-(3,4-dimethoxy-phenyl)-hydroxy-methyl]-N,N-dimethyl-butyramide 
• 77516-03-1 (5S,6R,7S)-5-(3,4-Dimethoxy-phenyl)-7-methyl-8-oxo-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid dimethylamide 
• 77516-03-1 (5S,6R,7R)-5-(3,4-Dimethoxy-phenyl)-7-methyl-8-oxo-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid dimethylamide 
• 77516-02-0 C₂₆H₃₁NO₅S₂ 
• 77516-04-2 (5S,6S,7R)-5-(3,4-Dimethoxy-phenyl)-7-methyl-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid dimethylamide 
• 56579-86-3 2-(3,4-methylenedioxyphenyl)-1,3-dithiane 
• 77-78-1 dimethyl sulfate 
• 59985-35-2 4-((5R,6R,7S)-6,7-Dimethyl-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxol-5-yl)-2-methoxy-phenol 
• 78919-30-9 chicanine methyl ether 
• 78919-28-5 (+)-chicanine 

Relevant articles and documents

A sterically encumbered photoredox catalyst enables the unified synthesis of the classical lignan family of natural products

Herein, we detail a unified synthetic approach to the classical lignan family of natural products that hinges on divergence from a common intermediate that was strategically identified from nature's biosynthetic blueprints. Efforts toward accessing the common intermediate through a convergent and modular approach resulted in the discovery of a sterically encumbered photoredox catalyst that can selectively generate carbonyl ylides from electron-rich epoxides. These can undergo concerted [3 + 2] dipolar cycloadditions to afford tetrahydrofurans, which were advanced (2-4 steps) to at least one representative natural product or natural product scaffold within all six subtypes in classical lignans. The application of those synthetic blueprints to the synthesis of heterolignans bearing unnatural functionality was demonstrated, which establishes the potential of this strategy to accelerate structure-activity-relationship studies of these natural product frameworks and their rich biological activity.

ABSOLUTE CONFIGURATION OF THE LIGNAN OLEIFERINS FROM VIROLA OLEIFERA

The assignment of the absolute configuration for the lignan-7-ols, (7R,8S,8'R)-olieferins A-C, was established by acid catalysed Friedel-Crafts-type cyclization for the known 2,7'-cyclolignans and chemical analyses.

TANDEM CONJUGATE ADDITION-α-ALKYLATION OF UNSATURATED AMIDES. SYNTHESIS OF 1-ARYLTETRALIN LIGNANS

The amide alcohols 5,6, obtained in one step from the sequential reaction of N,N-dimethylcrotonamide with dithiane 3 anion and aryl aldehyde 4, were efficiently converted into the lignans galcatin (2a) and isogalcatin (2b).