101860-51-9

Basic information

• Product Name: (R)-3-(4-methoxybenzyl)-4-acetylthiazolidin-2-one
• Synonyms: (R)-3-(4-methoxybenzyl)-4-acetylthiazolidin-2-one;(R)-4-ACETYL-3-(4-METHOXYBENZYL)THIAZOLIDIN-2-ONE
• CAS NO: 101860-51-9
• Molecular Formula: C₁₃H₁₅NO₃S
• Molecular Weight: 265.08
• Product Categories: Heterocycles
• Mol File: 101860-51-9.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 430.4 °C at 760 mmHg
• Flash Point: 214.1 °C
• Appearance: /
• Density: 1.267 g/cm³
• CAS DataBase Reference: (R)-3-(4-methoxybenzyl)-4-acetylthiazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-(4-methoxybenzyl)-4-acetylthiazolidin-2-one(101860-51-9)
• EPA Substance Registry System: (R)-3-(4-methoxybenzyl)-4-acetylthiazolidin-2-one(101860-51-9)

Safety Data

• Hazardous Substances Data: 101860-51-9(Hazardous Substances Data)

Usage

Description

(R)-3-(4-methoxybenzyl)-4-acetylthiazolidin-2-one is a thiazolidinedione chemical compound characterized by a thiazolidine ring structure, an acetyl group, and a benzyl group with a methoxy substituent. As a member of the thiazolidinedione class, it is known for its potential role in treating type 2 diabetes mellitus by enhancing insulin sensitivity and reducing blood sugar levels. The specific presence of the methoxybenzyl and acetyl groups may impart unique pharmacological properties to this compound, making it a promising candidate for drug development and research. The (R)designation highlights its stereochemistry, which is crucial for understanding its three-dimensional structure and potential biological activity. Further investigation is required to fully explore the compound's capabilities and applications.

Uses

Used in Pharmaceutical Industry:
(R)-3-(4-methoxybenzyl)-4-acetylthiazolidin-2-one is used as a potential therapeutic agent for the treatment of type 2 diabetes mellitus. Its mechanism of action involves increasing the body's sensitivity to insulin, which helps in lowering blood sugar levels. The presence of the methoxybenzyl and acetyl groups may contribute to its efficacy and selectivity, offering a novel approach to diabetes management.
Used in Drug Development Research:
(R)-3-(4-methoxybenzyl)-4-acetylthiazolidin-2-one serves as a valuable subject for drug development research due to its unique structural features and potential pharmacological properties. The methoxybenzyl and acetyl groups may provide opportunities for optimizing the compound's activity, selectivity, and pharmacokinetic profile. Researchers can explore its potential applications in various therapeutic areas, including but not limited to diabetes treatment, by investigating its interactions with biological targets and evaluating its safety and efficacy in preclinical and clinical studies.
Used in Chemical Synthesis:
(R)-3-(4-methoxybenzyl)-4-acetylthiazolidin-2-one can be utilized as a key intermediate or building block in the synthesis of other complex organic molecules, particularly those with potential pharmaceutical or biological applications. Its unique structural features, including the thiazolidine ring and functional groups, make it a versatile component in organic synthesis, allowing for the development of novel compounds with diverse properties and applications.

Upstream product

• 911040-40-9 (R)-N-methoxy-3-(4-methoxybenzyl)-N-methyl-2-oxothiazolidine-4-carboxamide 
• 676-58-4 methylmagnesium chloride 
• 75-16-1 methylmagnesium bromide 
• 2746-25-0 p-Methoxybenzyl bromide 
• 824-94-2 p-methoxybenzyl chloride 
• 101860-50-8 (-)-3-(4-methoxybenzyl)-2-oxo-thiazolidine-4-carboxylic acid ethyl ester 
• 139944-38-0 (-)-3-(4-methoxybenzyl)-2-oxo-thiazolidine-4-carboxylic acid 
• 646994-31-2 (S)-3-(4-Methoxy-benzyl)-2-oxo-thiazolidine-4-carbonyl chloride 

Downstream Products

• 101860-56-4 (R)-4-[3-Hydroxy-4-((2R,3R,7R,10S)-2,3,10-trimethyl-1,4,6-trioxa-spiro[4.5]dec-7-yl)-butyryl]-3-(4-methoxy-benzyl)-thiazolidin-2-one 
• 861821-49-0 (2Z,6E)-3-Methyl-deca-2,6-dien-8-ynoic acid (2R,4R,6R)-2-methoxy-2-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-6-((S)-3-methyl-hex-4-ynyl)-tetrahydro-pyran-4-yl ester 
• 928112-42-9 4-[2,4-dihydroxy-6-(3-methyl-hex-4-ynyl)-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyl)-thiazolidin-2-one 
• 646994-48-1 4-[2,4-dihydroxy-6-(3-methyl-hex-4-ynyl)-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyl)-thiazolidin-2-one 
• 76343-93-6 latrunculin A 
• 76343-94-7 latrunculin B 
• 101915-87-1 6,7-(Z)-N-PMB-15-OMe-Latrunculin B 
• 646994-49-2 (R)-4-[(2R,4S,6R)-4-Hydroxy-2-methoxy-6-((S)-3-methyl-hex-4-ynyl)-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyl)-thiazolidin-2-one 
• 1053714-70-7 Trifluoro-methanesulfonic acid (2R,4S,6R)-2-methoxy-2-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-6-((S)-3-methyl-hex-4-ynyl)-tetrahydro-pyran-4-yl ester 
• 646994-51-6 (R)-3-(4-Methoxy-benzyl)-4-((Z)-(1R,10S,13R,15R)-15-methoxy-5,10-dimethyl-3-oxo-2,14-dioxa-bicyclo[11.3.1]heptadec-4-en-8-yn-15-yl)-thiazolidin-2-one 
• 928112-44-1 (Z)-3-Methyl-oct-2-en-6-ynoic acid (2R,4R,6R)-2-methoxy-2-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-6-((S)-3-methyl-hex-4-ynyl)-tetrahydro-pyran-4-yl ester 
• 911040-45-4 (R)-4-((2R,4R,6R)-2,4-dihydroxy-6-(pent-4-enyl)-tetrahydro-2H-pyran-2-yl)-3-(4-methoxybenzyl)thiazolidin-2-one 
• 911040-46-5 (R)-4-((2R,4S,6R)-2,4-dihydroxy-6-(pent-4-enyl)-tetrahydro-2H-pyran-2-yl)-3-(4-methoxybenzyl)thiazolidin-2-one 
• 1056194-56-9 (R)-4-((2R,4S,6R)-2,4-dihydroxy-6-((S)-3-methylpent-4-enyl)-tetrahydro-2H-pyran-2-yl)-3-(4-methoxybenzyl)thiazolidin-2-one 

Relevant articles and documents

Divergent approach to building a latrunculin family derived hybrid macrocyclic toolbox

A divergent approach to obtain a latrunculin family based hybrid macrocyclic toolbox is developed. A practical, stereoselective synthesis of a common substructure present in latrunculin A and latrunculol A was achieved. This was further utilized in the ma

PROCESS FOR THE PREPARATION OF 3,4-DISUBSTITUTED-THIAZOLIDIN-2-ONES

The present invention is directed to practical high-yielding synthetic processes for preparing 3,4-disubstituted-thiazolidin-2-ones, which do not compromise the absolute stereochemical integrity of the compounds. The present invention is also directed to

Selective iron-catalyzed cross-coupling reactions of Grignard reagents with enol triflates, acid chlorides, and dichloroarenes

Cheap, readily available, air stable, nontoxic, and environmentally benign iron salts such as Fe(acac)3 are excellent precatalysts for the cross-coupling of Grignard reagents with alkenyl triflates and acid chlorides. Moreover, it is shown that dichloroarene and -heteroarene derivatives as the substrates can be selectively monoalkylated by this method. All cross-coupling reactions proceed very rapidly under notably mild conditions and turned out to be compatible with a variety of functional groups in both reaction partners. A detailed analysis of the preparative results suggests that iron-catalyzed C-C bond formations can occur via different pathways. Thus, it is likely that reactions of methylmagnesium halides involve iron-ate complexes as the active components, whereas reactions of Grignard reagents with two or more carbon atoms are effected by highly reduced iron-clusters of the formal composition [Fe(MgX)2]n generated in situ. Control experiments using the ate-complex [Me4Fe]Li2 corroborate this interpretation.