101979-45-7

Basic information

• Product Name: (S)-1-(4-isopropyl-2-thioxothiazolidin-3-yl)ethanone
• Synonyms: (S)-1-(4-isopropyl-2-thioxothiazolidin-3-yl)ethanone;(S)-3-Acetyl-4-isopropylthiazolidine-2-thione;1-[(4S)-4-(1-Methylethyl)-2-thioxo-3-thiazolidinyl]-ethanone
• CAS NO: 101979-45-7
• Molecular Formula: C₈H₁₃NOS₂
• Molecular Weight: 203.32492
• EINECS: -0
• Mol File: 101979-45-7.mol
• Article Data: 15

Chemical Properties

• Melting Point: 67-68℃ (dichloromethane )
• Boiling Point: 279.6±23.0 oC (760 Torr), Calc.*
• Flash Point: 122.9±22.6 oC, Calc.*
• Appearance: /
• Density: 1.22±0.1 g/cm3 (20 oC 760 Torr), Calc.*
• CAS DataBase Reference: (S)-1-(4-isopropyl-2-thioxothiazolidin-3-yl)ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-(4-isopropyl-2-thioxothiazolidin-3-yl)ethanone(101979-45-7)
• EPA Substance Registry System: (S)-1-(4-isopropyl-2-thioxothiazolidin-3-yl)ethanone(101979-45-7)

Safety Data

• Hazardous Substances Data: 101979-45-7(Hazardous Substances Data)

Usage

General Description

The chemical "(S)-1-(4-isopropyl-2-thioxothiazolidin-3-yl)ethanone" is a compound with the molecular formula C8H13NOS2. It is a thiazolidinone derivative with a chiral center and a ketone functional group. (S)-1-(4-isopropyl-2-thioxothiazolidin-3-yl)ethanone is commonly used in the synthesis of pharmaceuticals and agrochemicals due to its potential biological activities. Its molecular structure suggests that it may act as a thiazolidinone-based inhibitor for certain enzymes or receptors in biological systems. Additionally, its isopropyl group may provide steric hindrance or specific interactions in chemical reactions or binding interactions with target molecules. Further study is needed to fully understand the potential applications and impacts of this chemical compound.

Upstream product

• 76186-04-4 (S)-4-isopropylthiazolidine-2-thione 
• 75-36-5 acetyl chloride 
• 7137-32-8 acetic pivalic mixed anhydride 
• 2026-48-4 (S)-valinol 
• 72-18-4 L-valine 
• 75-15-0 carbon disulfide 

Downstream Products

• 101979-53-7 (E,S)-3-hydroxy-1-((S)-4-isopropyl-2-thioxothiazolidin-3-yl)-5-phenylpent-4-en-1-one 
• 101979-49-1 (E,R)-3-hydroxy-1-((S)-4-isopropyl-2-thioxothiazolidin-3-yl)-5-phenylpent-4-en-1-one 
• 117606-75-4 (S)-2-Methyl-3-oxo-2-phenyl-butyric acid tert-butyl ester 
• 194342-72-8 (S)-5-(2-Bromo-benzyloxy)-3-hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-pentan-1-one 
• 194342-94-4 (3S,5S)-7-(2-Bromo-benzyloxy)-3-hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-5-(tetrahydro-pyran-2-yloxy)-heptan-1-one 
• 194294-67-2 (3S,5R)-3-Hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-5-(4-methoxy-benzyloxy)-6-(2-trimethylsilanyl-ethoxymethoxy)-hexan-1-one 
• 264889-47-6 (E)-(3R,6S,9R)-9-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-6-methoxymethoxy-dec-4-en-1-one 
• 375826-94-1 (E)-(3R,6S,7S)-7-Benzyloxy-3-hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-6,8-dimethyl-non-4-en-1-one 
• 667419-28-5 (4S)-N-[(3R)-3-[3-((1S)-1-tert-butyldimethylsilyloxy-3-butynyl)phenyl]-3-hydroxypropanoyl]-4-isopropyl-1,3-thiazolidine-2-thione 

Relevant articles and documents

Synthetic studies towards lagunamide C: Polyketide assembly investigations

Lagunamide C is a depsipeptide natural product with low nM cytotoxicity towards numerous cancer cell lines. Synthetically, it is disconnected to a pentapeptide backbone and polyketide unit that possesses four stereogenic centers, of which two of centers are in question (C38 & 40). Our model system highlights a high-selective aldol addition via a Crimmin's auxiliary setting the C40 ester linkage, and a non-facially selective cyclopropanation with subsequent ring opening for the installation of the C38 methyl center.

Stereoselective synthesis of maresin 1

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Isolation, Structure Elucidation, Biosynthesis, and Synthesis of Antalid, a Secondary Metabolite from Polyangium species

The isolation, structure elucidation, and synthesis of antalid (1), a novel secondary metabolite from Polyangium sp., is described herein. The structure elucidation of 1 was performed with the aid of mass spectrometry, high field NMR experiments, and crystal structure analysis. The absolute configuration of antalid was confirmed through the Mosher ester method and ultimately by total synthesis. In addition, the biosynthetic origin of this hybrid PKS-NRPS natural product was unraveled by the in silico analysis of its biosynthetic gene cluster.

Total Enantioselective Synthesis of the Endophytic Fungal Polyketide Phomolide H and Its Structural Revision

A total synthesis of the proposed structure of the natural polyketide-macrolactone phomolide H 2 has been achieved following a bidirectional strategy from l-tartaric acid. The originally assigned structure of phomolide H displayed discordant NMR spectroscopic data in comparison with synthetic 2. The synthetic strategy was extended to prepare diastereomers and epimeric methyl-ethers of the natural product, structural analysis of which revealed a match of the natural product with diastereomer 27. The structural revision of phomolide H from 2 to the methanol solvate of compound 27 is presented.

Ambruticins: tetrahydropyran ring formation and total synthesis

The ambruticins are a family of polyketide natural products which exhibit potent antifungal activity. Gene knockout experiments are in accord with the proposal that the tetrahydropyran ring of the ambruticins is formedviathe AmbJ catalysed epoxidation of the unsaturated 3,5-dihydroxy acid, ambruticin J, followed by regioselective cyclisation to ambruticin F. Herein, a convergent approach to the total synthesis of ambruticin J is described as well as model studies involving epoxidation and cyclisations of unsaturated hydroxy esters to give tetrahydropyrans and tetrahydrofurans. The total synthesis involves preparation of three key fragments which were unitedviaa Suzuki-Miyaura cross-coupling and Julia-Kocienski olefination to generate the required carbon framework. Global deprotection to a triol and selective oxidation of the primary alcohol gave, after hydrolysis of the lactone, ambruticin J.