50766-67-1

Basic information

• Product Name: 2-(3,4-DIMETHOXY-PHENYL)-[1,3]DITHIANE
• Synonyms: 2-(3,4-DIMETHOXY-PHENYL)-[1,3]DITHIANE
• CAS NO: 50766-67-1
• Molecular Formula: C₁₂H₁₆O₂S₂
• Molecular Weight: 256.38424
• Mol File: 50766-67-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(3,4-DIMETHOXY-PHENYL)-[1,3]DITHIANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,4-DIMETHOXY-PHENYL)-[1,3]DITHIANE(50766-67-1)
• EPA Substance Registry System: 2-(3,4-DIMETHOXY-PHENYL)-[1,3]DITHIANE(50766-67-1)

Safety Data

• Hazardous Substances Data: 50766-67-1(Hazardous Substances Data)

Upstream product

• 109-80-8 1.3-propanedithiol 
• 120-14-9 3,4-dimethoxy-benzaldehyde 

Downstream Products

• 99545-24-1 2-(2,2-dimethoxyethyl)-2-(3,4-dimethoxyphenyl)-1,3-dithiane 
• 88939-59-7 2<2-(1-tosyl-3,4,4-trimethylimidazolidinyl)>-3,4-dimethoxyphenyl-1,3-dithiane 
• 62096-77-9 4-[2-(3,4-Dimethoxy-phenyl)-[1,3]dithian-2-yl]-dihydro-furan-2-one 
• 1446846-73-6 (S)-1,5-bis((2-(3,4-dimethoxyphenyl)-1,3-dithian-2-yl)methyl)pyrrolidin-2-one 
• 1446846-74-7 (S)-1,2,8,8a-tetrahydro-6,7-bis(3,4-dimethoxyphenyl)-indolizin-3(5H)-one 
• 26503-67-3 (S)-1,2,3,5,8,8a-hexahydro-6,7-bis(3,4-dimethoxy-phenyl)indolizine 
• 138596-87-9 (2''S)-2-(3',4'-Dimethoxyphenyl)-2-(N-t-butoxycarbonyl-2''-methylenepyrrolidine)-1,3-dithiane 
• 106053-24-1 2-deutero-2-(3,4-dimethoxyphenyl)-1,3-dithiane 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 104072-34-6 2-(3,4-Dimethoxy-phenyl)-2-pent-4-enyl-[1,3]dithiane 
• 155855-91-7 2-(3,4-dimethoxyphenyl)-2-<4-<(tert-butyldimethylsilyl)oxy>-3-methoxybenzyl>-1,3-dithiane 
• 102349-11-1 2-hydroxy-1-(3,4-dimethoxyphenyl)-2-(2-<β-(N-ethoxycarbonyl-N-methyl)aminoethyl>-4,5-methylenedioxyphenyl)-ethanone 1,3-propylenedithioacetal 
• 25001-57-4 justicidin A 
• 442-33-1 (-)-(2S)-2-[2-(3,4-dimethoxyphenyl)ethyl]-1-methyl-1,2,3,4-tetrahydroquinoline 

Relevant articles and documents

Visible-light mediated facile dithiane deprotection under metal free conditions

Visible light mediated facile and selective dithiane deprotection under metal free conditions is developed. Eosin Y (1 mol%) proved to be an effective catalyst for the dithiane deprotection under the ambient photoredox conditions. The standard household compact fluorescent light source (CFL bulb) proved to be effective under open-air conditions in aqueous acetonitrile at room temperature. The protocol that exhibits a broad substrate scope and functional group tolerance has been shown to expand to a range of transformations for the electron-rich and -deficient thioacetals and thioketals. The synthetic utility of this protocol has also been demonstrated by gram-scale application.

Dehydrative Glycosylation Enabled by a Comproportionation Reaction of 2-Aryl-1,3-dithiane 1-Oxide?

A new dehydrative glycosylation reaction has been established by capitalizing on the comproportionation reaction of 2-aryl-1,3-dithiane 1-oxides promoted by triflic anhydride (Tf2O). By wedding the high potency of thiophilic promoter system with the step efficiency of dehydrative glycosylation, this reagent underwent facile intermolecular oxothio acetalization with C1-hemiacetal donor to install a temporary leaving group, rendering a transient electrophilic center at the remote site to the anomeric position. The sulfenyl triflate tethered at the terminus concomitantly activated the sulfide intramolecularly to afford the oxocarbenium ion, thereby facilitating the title glycosylation. Aside from accommodating broad range functional groups and inactive hemiacetal substrates, the present activation protocol also proved expedient for 1,3-diol protection. Most importantly, this method further provided a fresh perspective for the application of sulfur chemistry to carbohydrate chemistry.

Design, synthesis, and evaluation of DNA topoisomerase II-targeted nucleosides

We developed novel nucleoside-based topoisomerase II selective inhibitors and showed that small structural units, such as catechols, are essential for DNA topoisomerase II inhibitory activity. Moreover, nucleoside analogues containing TBS and 1,3-dithian

Design and synthesis of novel arctigenin analogues for the amelioration of metabolic disorders

Analogues of the natural product (-)-arctigenin, an activator of adenosine monophosphate activated protein kinase, were prepared in order to evaluate their effects on 2-deoxyglucose uptake in L6 myotubes and possible use in ameliorating metabolic disorders. Racemic arctigenin 2a was found to display a similar uptake enhancement as does (-)-arctigenin. As a result, the SAR study was conducted utilizing racemic compounds. The structure-activity relationship study led to the discovery of key substitution patterns on the lactone motif that govern 2-deoxyglucose uptake activities. The results show that replacement of the para-hydroxyl group of the C-2 benzyl moiety of arctigenin by Cl has a pronounced effect on uptake activity. Specifically, analogue 2p, which contains the p-Cl substituent, stimulates glucose uptake and fatty acid oxidation in L6 myotubes.

Synthesis of chiral α-diarylacetic esters by stereospecific 1,2-aryl migration promoted by in situ generated acetals from benzoins

A simple protocol for the synthesis of α-diarylacetic esters from benzoins is described. In situ generated acetal assists rapid 1,2-aryl migration in a stereospecific manner, paving the way to make enantioenriched α-diarylacetic esters from easily accessi

Synthesis of (+)-septicine using intramolecular McMurry coupling: A Chiron approach

Total synthesis of secophenanthroindolizidine alkaloid (+)-septicine 1 was accomplished using the McMurry coupling for the construction of indolizidine ring, using L-glutamicacid as chiral source. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.

Silica-supported phosphorus pentoxide: A reusable catalyst for S,S-acetalization of carbonyl groups under ambient conditions

Phosphorus pentoxide supported on silica gel (P2O 5/SiO2) efficiently acts as a highly active and reusable catalyst for cyclic and non-cyclic S,S-acetalization of a variety of carbonyl compounds under mild, solvent-free an

Oxidative deprotection of 1,3-dithiane group using NaClO2 and NaH2PO4 in aqueous methanol

The 1,3-dithiane group was oxidatively deprotected under the conditions of sodium chlorite, sodium dihydrogenphosphate, and 2-methyl-2-butene in 3:1 methanol-water at room temperature in good yield.

Chemoselective thioacetalisation and transthioacetalisation of carbonyl compounds catalysed by tetrabutylammonium tribromide (TBATB)

Thioacetals and thioketals of various aldehydes and ketones were obtained directly from carbonyl compounds or by a transthioacetalisation process from cyclic O,O-acetals in the presence of dithiols and a catalytic amount of tetrabutylammonium tribromide (TBATB). Chemoselective thioacetalisation of aromatic aldehydes containing an electron-donating group in the presence of an aldehyde containing an electron-withdrawing group, aldehydes in the presence of ketones, aliphatic cyclic ketones in the presence of aromatic ketones and less hindered ketones in the presence of more hindered ketones have been achieved. A cyclic acetal containing an electron-donating group has been chemoselectively transthioacetalised in the presence of an acetal having an electron-withdrawing substituent. These selectivities are due to the intrinsic reactivity of the substrate themselves and are independent of the catalyst and reaction conditions, Shorter reaction times, mild reaction conditions, stability of acid sensitive protecting groups, high efficiencies, facile isolation of the desired products and the catalytic nature of the reagent are the attractive features of the present method.

Synthesis of acylsilanes via oxidative hydrolysis of 2-silyl-1,3-dithianes mediated by N-bromosuccinimide

The oxidative method for the hydrolysis of 1,3-dithianes was applied to 2-silyl-1,3-dithianes using N-bromosuccinimide providing acylsilanes with good yields under a short reaction period. The oxidation of aroylsilanes to carboxylic acid was prevented by